The 25 Most Influential Shoes and Bags

After debating the most impactful women’s and men’s fashion since World War II as part of our T 25 series, we decided to ask five members of the American fashion community to each nominate 10 accessories they felt were worthy of being on a list of the 25 most influential shoes and handbags of the past 100 years. Our group of panelists spanned over four decades of experience in the industry and included the stylist and T contributing editor Ian Bradley; the author and former creative director of Barneys New York Simon Doonan; the creative director and founder of the accessories label Brother Vellies, Aurora James; the senior vice president for creative merchandising of Nordstrom, Olivia Kim; and the founder and designer of the fashion brand Luar, Raul Lopez.

On a cold evening last December, the jury convened on a video call — which ended up lasting two-and-a-half hours — to wrangle over the 50 shoes and handbags they’d put forth. Some nominations were rejected, either because the group felt a piece hadn’t substantially informed what came after it or because it didn’t meet the list’s two criteria: the accessory must have been designed after 1925 and sold in stores. That latter rule disqualified Alexander McQueen’s nearly 12-inch-high Armadillo platform heels; although they challenged the standards of shoe shape and height at the time (some models reportedly refused to wear them on the runway in 2009, for fear of injury), they were never available to the public. Other propositions were met with unanimous approval, such as Fendi’s 1997 Baguette bag. The 2001 Le City bag and a pair of 2007 “Lego” heels from Nicolas Ghesquière’s 15-year tenure at Balenciaga took two spots, making him the only designer with multiple items on the list.

The 25 selected pieces, which appear not ranked by their importance but in the rough order they were discussed, come from almost every decade since the 1930s (excepting the 1940s and 2020s). Discussed with particular enthusiasm were the picks from the 1990s and early aughts, which made sense, the group concluded: the ’90s were when the idea of the It bag was born, ushering in an era in which status-symbol accessories would permeate pop culture, with Real Housewives and Kardashians wearing Louboutins and carrying Hermès Birkins on TV.

But though we still live in that age, the hysteria around shoes and handbags may have peaked in a 2000 episode of the HBO series “Sex and the City,” in which Sarah Jessica Parker’s character, Carrie Bradshaw, wearing a pair of towering heels and a purple sequin-encrusted Fendi purse, is mugged at gunpoint. When told to hand over her “bag,” she corrects the thief: “It’s a Baguette.” — Alexa Brazilian

This conversation has been edited and condensed. Though numbered, the entries below aren’t ranked; their order reflects the course of the panelists’ conversation.

Before Martin Margiela made clothes, he designed shoes for a boutique in Antwerp, Belgium. So when he staged his first ready-to-wear runway show in Paris, in 1988, at age 31, he paired the deconstructed garments for which he would become known — like jackets and vests made inside out so their seams became graphic design details — with equally conceptual footwear. Inspired by the image of a bare foot resting atop a high heel, he looked to the Japanese tabi (“foot bag”). The style, which separates the wearer’s big toe from the other four — the division is thought to improve balance — evolved from traditional socks often worn with thong sandals. To achieve his desired “naked” look, Margiela crafted booties, some flesh-colored, in slightly crinkled leather and suede, and affixed them to rounded, stacked-wood heels. To economize, he reused the same samples for several seasons, until they eventually became a signature — and a best seller. For the next two decades, Margiela regularly reinterpreted the style, presenting split-toed ballet flats, sneakers and pumps. In 2023, 35 years after its introduction, the tabi was at the center of a social media scandal when a woman accused her Tinder date of stealing her pair and giving them to his girlfriend. Commenters were outraged. — Jameson Montgomery

Aurora James: It might be among the 25 most beloved shoes, but I don’t know that it’s been that influential. You guys can argue with me.

Ian Bradley: It’s definitely the most recognizable fashion shoe.

Raul Lopez: But it’s also a Japanese shoe that’s been around for hundreds of years. We all get inspiration from everywhere, but let’s be honest: The tabi is a Japanese worker’s garden shoe.

Simon Doonan: I think it’s one of those shoes, like the [Alexander McQueen] Armadillo, that just raises the bar on what’s possible. It’s influential that way.

Alexa Brazilian: I agree that while someone might not be copying this silhouette, it really paved the way for someone like Phoebe Philo and all her ugly-pretty shoe designs.

Bradley: Especially that round heel.

Brazilian: It did open the door for others.

James: But did it? Or was it the original Japanese shoe [that did]?

Considered by many to be the prototypical canvas carryall, the L.L. Bean Boat and Tote was introduced by the Maine-based outfitter in 1965 as a relaunch of a 1944 design. The Ice Carrier, as the bag was originally known, was designed with a double-layer bottom for transporting block ice before the rise of home freezers. Still made from the same undyed, oatmeal-hued canvas, the slimmer Boat and Tote retains its two-tone design (straps and bottom panels were originally available in either red or blue) and handles that can be slung over a shoulder. Though modestly priced (it sold for $4.75 in 1965 and costs less than $50 today), it became associated with wealthy East Coast summer destinations like Nantucket and the Hamptons. Endless iterations — some zipper-topped, others with longer straps or interior pouches — have since come out in a range of colors and sizes. Monogramming was once as far as preppier clients would go to personalize their totes, but tongue-in-cheek embroidery (“Birkin,” “Oy Vey,” “Full of It”) has now become a trend with its own Instagram account (@ironicboatandtote). The core design, however, is unchanged, and the bags are still, according to the company, “handcrafted, one tote at a time, by a small team of stitchers in Maine.” — J.M.

Olivia Kim: This has been a template for lots of other brands and designers. It’s simple, easy and affordable — which I appreciate.

Doonan: I came to Barneys in 1985. Other than a bag like this, there was nothing for girls to carry their stuff to work in. That was before the era of bag mania. All the groovy chicks came to work with a canvas tote.

Lopez: I thought it was a status symbol. People from all these urban dystopias weren’t looking at it, but the man who traveled or lived a life of leisure, or the woman on the go, had a canvas tote bag.

Bradley: It was WASPy. Like, you’d have a [Hermès] Kelly inside your tote.

3. Birkenstock’s Arizona Sandal, 1973

Birkenstock can trace its history to Johannes Birkenstock, an 18th-century cobbler in the village of Langen-Bergheim, Germany. But it wasn’t until 1925 that his great-grandson Konrad had the then-radical idea of contouring insoles to the shape of feet — an innovation he patented under the name fußbett (“footbed”). Almost immediately, Birkenstocks were embraced by podiatrists, and in the 1960s the company started mass-producing the styles we know today. First released in 1973, the Arizona, Birkenstock’s most enduring model, is a genderless sandal with two adjustable, buckled straps attached to a jute, cork and latex sole. Although they were initially seen as an anti-fashion accessory, associated with hippies and retirees, two decades later they became a style statement: Marc Jacobs incorporated them into his spring 1993 Perry Ellis show, and actresses like Gwyneth Paltrow were often photographed wearing them. The Arizona has resurfaced lately, in collaborations with brands such as Manolo Blahnik and Valentino and in the 2023 film “Barbie,” in which the sandal is posited as the antidote to the pink high heel. — J.M.

James: I’d just die if these shoes didn’t make the list. There was never a day that my mom and my godmother weren’t wearing them. They’re so evocative to me of everything I hated about my mom and her hippie friends: the smell of cannabis and gardening. This is the shoe of people who’ve never had a pedicure. And the fact that nearly everyone has made their own version of this — myself included? I was literally wearing a version this morning that I did. I might hate putting them on sometimes, but I still put them on.

Kim: I appreciate their approachability. You can find them on Zappos or at Nordstrom. There are all these designers who’ve done their own versions and those who’ve done partnerships with [Birkenstock], whether it’s Manolo [Blahnik] or Rick Owens. I also appreciate their democratic-ness — people wear them lots of different ways. There are really crunchy people with crusty heels wearing these shoes who’ve actually climbed Mount Everest. Birkenstock celebrated its 250th anniversary last year — there aren’t many companies with that type of heritage that have created something accessible and influential.

Doonan: It’s interesting that the epitome of anti-fashion counterculture can be re-embraced in a postmodern way and done in a thousand iterations, including pink fur. That’s what’s so magical about fashion: things go round and round.

Telfar Clemens has been running his Brooklyn-based brand for 20 years, at first often selling his reworked cardigans, hoodies and sweatpants to New York artists and club kids. But the label attracted a broader fan base as a result of the 2014 introduction of its now-ubiquitous Shopping Bag. As the name suggests, the all-purpose, affordable, unisex tote was influenced by the silhouette of Bloomingdale’s paper carryalls, which made their debut in the 1970s and include sans-serif text indicating their sizes: “little,” “medium” or “big.” Telfar’s totes are also rectangular, but with a longer, cross-body strap and two top handles. Like their inspiration, they originally came in three sizes; there’s now a fourth option: “shmedium.” Made from a twill-lined polyurethane blend (a more expensive leather version also exists), the bag has been referred to as the “Bushwick Birkin” because of its popularity among Brooklyn creative types. But Clemens has made it clear that he’s not interested in catering to any one group: “It’s not for you,” says the Telfar slogan. “It’s for everyone.” — J.M.

James: As someone who’s done a ton of development on plant-based substitutes and spent most of my life being vegan, I applaud Telfar for making the first mainstream vegan [leather] bag.

Lopez: A fun fact: When Telfar received his first sample back in the day, I was the first person to see this bag. He wanted to make a leather bag, and the factory sent him what’s now called vegan leather. I was like, “Girl, this is PVC.” And he was like, “Are you sure?” And I said, “Yes, girl. This is a plastic bag. I think you should run with it.” Fast-forward, he’s literally where he is now because of a tote bag, which is so crazy.

James: When I first saw it, I was like, “Whoa. This is horrible.” But obviously I was wrong. Half the girls don’t even know it’s faux.

Kim: These things sell out. People wait in line and are refreshing their browsers for them. And the people I see on the subway with these — there’s no stereotype about the person carrying it. Some are fashion people, some look corporate.

Lopez: Moms on my block. White moms on my block.

Brazilian: It’s the only accessory by a Black designer on our list. I think we should talk about why that is.

James: It costs so much money to [make] an It bag. The majority of [fashion or design] businesses are founded by people with multigenerational wealth, or are funded by partners XYZ, so it takes a lot of money or a lot of social capital. And that just hasn’t been accessible for a community that hasn’t had a lot of generational wealth.

Bradley: For the Black consumer, it was nice to have a designer bag that was for us and by us.

5. Balenciaga’s “Lego” Heel, 2007

Though the fashion industry is more inclusive than it used to be, luxury clothing is still often geared toward the tall and the thin. This was particularly true in the late aughts, when prevailing silhouettes were unforgivingly tight. Likely because most shoppers couldn’t wear those clothes, designers increasingly turned their attention to footwear, striving to invent the next hit shoe. No style captures that phenomenon as clearly as Balenciaga’s closed-toe cage sandal, which debuted in the fall 2007 runway show. Conceived by Nicolas Ghesquière, the brand’s creative director at the time, in collaboration with the shoe and accessories designer Pierre Hardy, the so-called Lego heels were made of vividly hued plastic components that formed a detachable cage around their wearer’s foot. Belted pads at the toe and ankle were inspired by adjustable snowboard bindings. The sandals helped popularize flashy, high-concept heels and drew their share of imitators: In 2009, Balenciaga filed a lawsuit against the New York-based retailer Steve Madden for alleged copyright infringement, eventually arriving at an undisclosed settlement. — J.M.

Lopez: This reminded me of what Balenciaga tried to do with those [fall 2021] silver boots put together with screws. For me, both felt like a knight’s armor. I think this one influenced so many other shoe brands to step it up — and then it got knocked off by everybody. I love everything Nicolas did in that era, but this was such an aha moment, like, “I’m going to show you that I can make a nasty toe.”

Kim: This shoe was clearly ahead of its time. It looks like it was 3D printed.

Lopez: But it wasn’t. That’s why it’s so cool.

Kim: I’m a huge Ghesquière fan, too. And I remember seeing them styled with a bohemian floral shirt and crazy cargo pants with the silk pockets that everyone died for.

Lopez: Everybody wanted this shoe. It didn’t matter if you were white, Black, Asian, Latino. It didn’t matter what social class you came from. For my cousins in Long Island to want to wear a shoe like this — that says a lot.

6. Chanel’s Slingback Pump, 1957

In 1954, at age 71, Gabrielle “Coco” Chanel made one of the most remarkable comebacks in fashion history, reopening her Paris couture house 15 years after closing it at the beginning of World War II. (And after eluding any sanctions for her secret collaboration with the Nazis.) Before the war, her little black dresses and jersey sportswear had already changed the way women dressed; afterward, she introduced the hallmarks most associated with the brand today: quilted handbags, tweed suits and the two-toned slingback pump. The shoe, which debuted in 1957, was creamy beige and had a black toe cap to protect the paler leather from scuffs. After Karl Lagerfeld joined the maison as creative director in 1983, he made the cap toe, which had been embraced by everyone from Park Avenue socialites to actresses like Catherine Deneuve and Jane Fonda, a Chanel signature, reinterpreting the look with ballet flats, boots, sandals and even sneakers over the course of his 36-year tenure. But for his fall 2015 Chanel show, Lagerfeld went back to basics, putting each model in a block-heeled version of the buff-and-black original. — Megan O’Sullivan

James: Although it’s not necessarily something I’d wear, for a whole set of women, if they’re going to spend money on something, this is the first expensive shoe they get.

Brazilian: It was the first real It slingback. And revolutionary for its combination of practicality and beauty.

James: This Chanel shoe, whether it’s the flat or the slingback, inspired the Tory Burch flat and a lot of other shoes that have surpassed hundreds of millions of dollars in revenue. It’s a hyper-recognizable, easy-to-wear everyday shoe, and an office shoe. This was and still is that shoe for many people.

7. Gucci’s Horse-Bit Loafer, 1953

In 1953, weeks after the death of Gucci’s founder, Guccio Gucci, who’d started the company in 1921, three of his sons — Aldo, Vasco and Rodolfo — traveled to Manhattan for the opening of the brand’s first store outside of Italy. While abroad, Aldo noticed the popularity of the penny loafer among American men and decided that Gucci should make its own version. Rather than having a coin slot, Gucci’s leather slip-ons — which were cut, sewn and hammered by hand — featured a horse bit, a motif introduced a few years earlier by Guccio, who had an interest in equestrian style. Francis Ford Coppola wore them while directing the first two “Godfather” movies in the 1970s, New York’s Metropolitan Museum of Art added them to its permanent collection in the ’80s, and by the ’90s they were so ubiquitous on Wall Street that they were known as “deal sleds.” When Tom Ford took artistic control of the brand in 1994, the loafer underwent a series of makeovers, emerging with a square toe one season and a logo print the next. Future creative directors followed his lead, with Alessandro Michele reinterpreting the shoe for fall 2015 as a shearling-lined slide and Sabato De Sarno, who stepped down earlier this month, adding platform heels to his spring 2024 version. — M.O.

Bradley: I’d say that Alessandro’s greatest achievement at Gucci was doing the horse-bit loafer slide. He brought a classic into the modern age by making it a fur-lined slide.

Doonan: When Alessandro was working his magic at Gucci, I was in heaven. It was so orgasmic and fabulous. Anything felt possible.

Brazilian: But since the shoe was first designed in 1953, I think we should do the original.

Doonan: I agree.

8. Manolo Blahnik’s BB Pump, 2008

Even as a child, Manolo Blahnik was obsessed with footwear: Growing up in the Canary Islands, he’d make tinfoil booties for garden lizards. In his 20s, he studied to be a set designer, but a 1969 meeting with the fashion editor Diana Vreeland put him on a different path; three years later, he was presenting his first shoe collection in London as part of an Ossie Clark fashion show. For the half-century since, “Manolos” have been a red-carpet mainstay. The best-selling BB style, created in 2008, is a pointed-toe court pump with a low-cut top line and a wrapped stiletto heel inspired by, Blahnik has said, the 1950s and ’60s style of Brigitte Bardot. As Madonna once noted, “Manolo Blahnik’s shoes are as good as sex. And they last longer.” — Kin Woo

Bradley: A suede BB pump is what my mom’s best friend comes to New York to buy.

Kim: I’m not a Manolo person, but women talk about how incredibly comfortable they are.

Doonan: They’re classically beautiful and have that wonderful enduring simplicity. I love the playful madness of fashion, the surprise and the explosive creativity. But there’s also room for a drumbeat of elegance.

Though Salvatore Ferragamo was only 25 when he opened the Hollywood Boot Shop, his second American store, in 1923, he was already a veteran shoemaker. At age 9, he’d created his first pair of shoes — for his sister’s first communion — and by 12, he began selling shoes out of his parents’ home in the small southern Italian town of Bonito. After moving to California with some of his 12 brothers in 1915, he befriended actresses like Mary Pickford, and in 1938, he designed the shoe that solidified his own stardom: a wedge sandal with a three-and-a-half-inch cork platform covered in rainbow-hued suede stripes, for Judy Garland. As one of the first Western designers to popularize the towering silhouette, Ferragamo inspired countless iterations including the platform go-go boots of the 1960s, the flamboyant disco shoes of the ’70s and ’80s and Vivienne Westwood’s 1993 Ghillie lace-ups. The original, complete with multicolored stitching and gold straps, remains in production. — M.O.

James: The Ferragamo platform was a fun, sexy, feminine shoe — and I feel like so many shoe designers are constantly referencing it.

Bradley: It shows what’s possible in an extreme way.

Doonan: And it’s an exquisite piece of design, especially the way the edges bevel. It’s really a masterpiece.

10. Kate Spade’s Sam Tote, 1993

In the early 1990s, Kate Spade, a young accessories editor at Mademoiselle magazine in New York, was on the hunt for a functional, everyday shoulder bag. Having come up short, she built a maquette from construction paper and Scotch tape and named her creation Sam, then produced it in black nylon and introduced it to the industry at a trade show in 1993. Barneys New York placed the first order, and, before long, seemingly every fashionable young Manhattanite owned one. Box-shaped with simple shoulder straps, the bag captured the era’s minimalist aesthetic: Its most identifiable feature was its rectangular, white-on-black Kate Spade label, which the designer stitched on the front rather than the inside. Early adopters included Mary-Kate and Ashley Olsen, but the tote’s legacy has less to do with celebrities than with women like Spade herself, who’d left her native Missouri in her youth with dreams of making it in New York. For many ambitious Generation Xers, buying a Sam was an important token of adulthood, a sign that they’d arrived. — M.O.

Bradley: When I was 10, it was the bag every girl carried. It was formal yet casual; a seventh grader could have it, but so could a grown woman.

Doonan: I remember when we launched them at Barneys in the ’90s. Kate [who died in 2018] was there. I know it’s hard to imagine now, but the idea of putting her name on the bag — not a wildly romantic name like Balenciaga — was quite daring. It was the beginning of companies starting to recognize the power of accessories, in the same way that perfume had become a point of access for a broader clientele.

Kim: I can’t not think about the ad campaigns and the way they made the working mom the focus, which was really different back then.

11. Comme des Garçons’ SA5100 Pouch, 1994

Sometime after founding Comme des Garçons in 1969, Rei Kawakubo started adding more affordable and slightly less experimental lines for those too timid to wear, say, a humpbacked top or a suit without armholes. Among those offerings was Comme des Garçons Wallet, a small collection of leather goods. In 1994, as part of that line, Kawakubo released a simple, rectangular pouch, which — at just over eight inches wide and six inches tall, with a zippered top — was possibly the most functional item she’d ever designed. The perfect size for a comb and a tube of lipstick or a passport and cash, it slid easily into a tote and could double as a clutch. The style caught on in Kawakubo’s corner of the fashion world, and a smaller version was later added to the collection. Both have been reimagined in various patterns, colors and materials, including polka dots, plaid, fluorescents and holographic silver leather. More than 30 years after its debut, it remains a symbol of erudite style. — M.O.

Kim: Rei Kawakubo is a god to me. We can’t have a conversation about influential fashion without thinking about her. This is the most simple, boring thing that she’s ever created, and yet it can be for everything. In a pinch, I’ve used it as a clutch. I also throw my toiletries in here. My young daughter uses it to store her Calico Critters.

Doonan: I have about five of their cross-body airline bags, and I carry all my tchotchkes in them everywhere I go.

Lopez: It’s such an understated bag because it’s so simple and doesn’t have a statement handle. But I’m one of those who’d wear it as an evening bag. I love that you can dress it up and down in your own way.

Introduced in 1978 by the Long Island-based shoe manufacturer Charles Cole, Candie’s targeted young female shoppers with campaigns featuring teen idols and commercials that looked and sounded like music videos. The brand’s defining style, the Candie slide was a wood-soled, open-toed sandal that came in a range of bright colors and — with a roughly four-inch, arched heel — transformed what had been an orthopedic silhouette into something to wear with a jean skirt and a going-out top. At the peak of the label’s popularity in the mid-80s, the company went so far as to assert that 1 in 4 American women owned a pair. In 1993, Candie’s was acquired by the brand management company Iconix International, which would bring in a succession of Y2K stars as spokespeople, including Destiny’s Child, Hilary Duff and Britney Spears. Today, with the re-emergence of ribbed tank tops, cargo pants and other archetypes of that era, Generation Z is discovering the slide anew. — Emilia Petrarca

Doonan: I used to live up the street from Frederick’s of Hollywood when they were making those stripper shoes. Hip girls would go buy them because they were dirt-cheap. And then fashion people discovered Candie’s. I believe Stevie Nicks used to come into [the L.A. boutique] Maxfield wearing the style. It was a way of being hotsy-totsy when you went out to a bar on a Friday night. They weren’t just trashy girls’ shoes.

Bradley: It’s kind of like what Sandy from “Grease” wore.

Brazilian: Oh yeah, when she has her makeover.

Bradley: They’re the ultimate bad-girl shoe.

13. Adidas’s Stan Smith Tennis Shoe, 1973

In 1972, Adidas asked the American athlete Stan Smith, then the world’s top tennis player, to endorse its first leather tennis shoe. Developed in the mid-60s — and known as the Haillet, after the French champion Robert Haillet; from 1973 to 1978, it was called the Stan Smith-Haillet — the sneaker was “considered high-tech,” as Smith told the Times in 2015, with better support, airflow and traction than its canvas predecessors. Smith’s agent negotiated to have his client’s face on the tongue, and Smith’s name replaced Haillet’s completely in 1978. By 1989, the shoe, with its white leather body, green accents and small perforations where the Adidas stripes would usually be, had sold some 22 million pairs worldwide. It even threatened to eclipse Smith’s sports legacy; his 2018 memoir is titled “Some People Think I’m a Shoe.” In 2001, a Jay-Z lyric suggested that Stan Smiths were synonymous with the country club set (the rapper also name-checked Gucci flip-flops and Izod bucket hats), but they were also embraced by fashion designers such as Marc Jacobs and Phoebe Philo (who made them a part of their personal uniforms) and Pharrell Williams (who collaborated on a pair in 2015). — E.P.

Doonan: This was the shoe that got women to wear sneakers in a fashion context.

Bradley: As a stylist, I think about how every brand does a generic Stan Smith shape. Phoebe Philo wore them.

Doonan: Even now, when my girlfriends say to me, “My boyfriend needs some groovy sneakers, what should he get?” I say, “Just get Stan Smiths.”

14. Prada’s Nylon Backpack, 1984

In 1975, when Miuccia Prada joined her grandfather Mario’s leather-goods business, one of her first ideas was a backpack — an accessory more closely associated with schoolchildren and hikers than with luxury fashion. With a degree in political science, Prada was more of a thinker than a designer, and her feminist politics influenced her aesthetics, too. “Any bourgeois subject that I approached, I always wanted to destroy it,” she told T in 2023. And so her backpack, which became available in 1984, wasn’t made of leather or exotic skins but of military-grade black nylon, a material best known for its use in parachutes. Often called the “Vela,” or “sail” in Italian, it had a single silver buckle attached to its front flap, where the brand’s triangular logo was prominently displayed. A minimalist statement, the pack, which now sells for about $2,300, became as covetable as any leather handbag, proving that the jolie-laide, or “pretty-ugly,” a term often applied to Prada’s style, could draw customers. The Vela has enjoyed remarkable staying power; today, there’s also a more sustainable recycled nylon version. — E.P.

Bradley: The idea of a designer backpack was very foreign then. Now, everyone makes one.

James: It was the beginning of a conversation: “If you just stick a logo on something, does it then have value?” And the answer seems to be yes. Is this a great bag? And do I own this bag? Yes and yes. I also think that it symbolized the power of brand identity in a way that reverberates to this day. You can just attach a campaign and a sense of identity to a product, regardless of material sourcing. I’m not dragging this bag, but I don’t know that the time, work and labor substantiated its price point as much as the logo did.

Introduced by Hermès in 1984, the Birkin might be the world’s most in-demand handbag, with an origin story that’s fashion legend. Earlier that year Jean-Louis Dumas, the French luxury house’s executive chairman, was seated next to the actress and singer Jane Birkin on a flight from Paris to London and witnessed her straw basket bag tumble to the floor, its contents scattering everywhere. Birkin complained about how hard it was to find a good, practical weekend bag; the two began exchanging ideas, and her namesake was born. Its briefcase-like design looks simple enough, but it can take Hermès artisans from 15 to 20 hours to hand-stitch each one. And although it was originally priced at $2,000, current styles — which vary in size (from about 8 to just under 16 inches), color (from classic saddle brown to bright orange) and material (from ostrich to alligator) — can cost hundreds of thousands of dollars, and, famously, there have been waiting lists just for the opportunity to buy one. Last year, a similar bag showed up on the Walmart website for less than $100. Dubbed the “Wirkin,” it sold out in no time. — E.P.

Doonan: The Birkin was an exclusive item that not many people knew about until the ’90s, when it became the signifier of glamour. Suddenly, this bag, which was relatively obscure, started showing up on every celebrity and fashion maven who entered every room purse-first.

Bradley: Yeah, it used to be, like, an undercover bag — the type a model would get after having a good season. And then it was everywhere.

Doonan: It’s interesting to note that prior to this bag’s existence, Jane Birkin carried everything in a rudimentary, rustic basket, which is what girls used to do. Before the handbag revolution, which happened in the ’90s and into the aughts, hip girls used to carry their stuff in a paper bag or shopping bag. A designer bag was [seen as too] conventional.

Kim: Its evolution is interesting, too. Jane wore it with all those charms and ribbons on it; that’s how that trend came about. The “purse-first” thing is so funny because women at the time were always carrying such big bags. They preceded you. Now it’s all about how small it can get.

16. Fendi’s Baguette Bag, 1997

Although Silvia Venturini Fendi, a granddaughter of the founders of the Rome-based fashion house, is Italian, her most famous handbag was inspired by the French. In 1997, after noticing Parisian women carrying bread under their arms, she created the Baguette, a slender purse with a short handle and Fendi’s signature double-F logo on the clasp. The bag has now been produced in over a thousand iterations: covered with sequins, embroidery, animal prints and logos. If Hermès’s Birkin became known for being hard to get, ample production of the Baguette allowed it to become one of the first true It bags. In 2022, 25 years after the bag’s release, Venturini Fendi said she considered the Baguette to be “a manifesto of identity and individuality, because it is always the same but always different.” — E.P.

Lopez: I have so many of these — with shells and crystals, the whole thing.

Brazilian: How many do you have?

Lopez: Twelve.

Doonan: Fendi found a groove with this bag shape. And then came the embroidered ones, beaded ones and artists’ collaborations. It was a whole thing. As a guy, I’m fascinated by how something like this can take off — women are coughing up thousands and thousands of dollars for these things. I always think about Sigmund Freud, who said something like “If you dream about handbags, those are vaginal symbols.” And if you think about it, it’s true — you don’t get to see inside your mother’s handbag, because it’s private and always held close to the body. When I see the Baguette, it’s always carried under the arm, almost like a secret.

Kim: Growing up in New York in the ’90s— it’s impossible to not think of the Fendi Baguette and hip-hop. You think about Lil’ Kim or Foxy Brown, who’d wear Fendi out at the clubs. I remember the first time I bought this bag, when I was in college. I’d saved all my money. I went straight to a club and felt so much a part of that scene.

Balenciaga’s very first handbag almost didn’t happen. Around 2000, after other labels started launching their best-selling bags, Balenciaga’s then-creative director, Nicolas Ghesquière, says he was instructed by the French conglomerate Groupe Jacques Bogart, which owned the brand at the time, to design one, too. What he came up with was a soft, patinated lambskin handbag with no logo, a slouchy structure and vintage-looking hardware — the opposite of the instantly recognizable, straightforwardly luxurious styles that were popular at the time. Convinced that the purse wouldn’t sell, the company decided not to produce it. But things changed after Kate Moss was seen with a rare prototype, and Le Dix Motorcycle Lariat, eventually known as Le City bag, came out in 2001. “It was a new, fresh thing, but it looked like an old, good, friendly thing,” Ghesquière said in 2011. — Tahirah Hairston

Bradley: It’s my number one. In the almost 25 years it’s been around, it’s never fallen out of style. It’s been done a million ways, but it still looks cool. I don’t think it ever became tacky.

Lopez: Actually, I think it fell off for a while after Nicolas left. I used to have a bunch of them, but I sold them all. Clearly, I didn’t think it was going to have a resurgence.

James: The idea that I could just throw it around and not be precious with it was so important to me. It felt like an expensive thing I’d splurged on, but also an accessory that I didn’t have to be gentle with — I hate being gentle with expensive things.

In Tommy Tucker’s 1964 song “Hi-Heel Sneakers,” the blues singer tells his lover to put on a pair of unusual shoes to “knock ’em dead” — both with her appearance and in case there’s a fight. Nineteen years later, the American designer Norma Kamali alluded to the song with a round-toe sneaker with prominent laces, a rubber toe cap and a tapered three-inch heel, somewhere between a stiletto and a Converse Chuck Taylor. Available in canvas or suede and in shades of red, yellow, green, blue, black and white, the shoes were released to go with Kamali’s 1980 Sweats collection, which also included sporty tops, dresses and pants. Looking back, Kamali seems to have anticipated the athleisure trend. “For the first time, casual clothing was worn to work, travel and on dates. The sneaker, to me, was a natural fit,” says Kamali, who patented the design in 1986. Other elevated athletic shoes followed — Isabel Marant’s Bekett wedges in 2011; Rihanna’s spike-heeled Fenty x Puma collaboration in 2017 — and in 2024, Sara Blakely, the founder of Spanx, debuted stiletto sneakers called Sneex. — T.H.

Lopez: Damn, I didn’t think about this one. It’s a good one.

Doonan: When everyone was buying their Kamali sweatsuits with shoulder pads, she also sold extraordinary, campy shoes that went with them. It was a very L.A. look. This shoe always stuck in my memory because it was such a postmodern mash-up of function and glamour and humor.

Kim: I think the high-low of it is interesting. It’s casual but dressy.

Bradley: And it basically predates all other sneaker heels. It’s a trailblazer.

19. Judith Leiber’s Chatelaine Clutch, 1967

A Hungarian-born Holocaust survivor, Judith Leiber married an American Army Signal Corps sergeant in 1946 and moved to the United States the following year. She started her own brand in 1963, after working on the assembly line for several handbag manufacturers. Determined to sell an affordable version of the small, gem-studded evening bags carried by royalty and aristocrats, in 1967 she designed a brass clutch, plated in gold or silver. But “when the samples came in,” she said, “it looked awful.” Her solution was to add Swarovski crystals to hide the bag’s flaws. She named the small, kiss-lock clutch the Chatelaine, and it became Leiber’s most popular creation. The success of that bag led her to create other whimsical, Swarovski-crystal-studded minaudières — small, formal clutches for holding makeup — shaped like animals, fruits or bunches of asparagus. “What she did was groundbreaking,” Harold Koda, the former head curator of the Costume Institute at the Metropolitan Museum of Art, said in 2017, a year before Leiber’s death. “She gave bags and purses a narrative.” — T.H.

James: I don’t have a strong emotional connection to this bag, but I think its influence runs deep. Everyone has tried to make their own version of it. And when I think of red carpets, I think of Judith Leiber.

Lopez: It’s the bag that you’d always think to wear to a gala. Everyone knows what this is. I have family members who know, and they’re not even in fashion. This shows the influence of TV shows like [the 2010-17 series] “Fashion Police.” I used to die for a Judith Leiber bag when I was growing up.

20. Carlos Falchi’s Butterfly Bag, 1979

In the 1970s, the Brazilian-born, New York-based designer Carlos Falchi took a relaxed approach to luxury handbags, which at the time were quite rigid and structured. “I didn’t really know how to make [one],” he said in 2008. “So I broke the rule[s].” The most iconic style he came up with was the Butterfly, a shoulder bag, sewn together with only two seams and gathered in the front to resemble an abstract butterfly, that came to be known as the Buffalo after its original material, buffalo hide. “It was soft and unstructured, had a long strap that allowed it to be slung around the body or over the arm — rather than carried like an object — and introduced a freedom and ease that mirrored the spirit of the era,” said Mellissa Huber, a curator at The Costume Institute at the Metropolitan Museum of Art. The Buffalo, which would come in a variety of exotic animal skins over the years and which, according to Women’s Wear Daily, was among the most imitated of the era, was inspired by Falchi’s time as an art student in Japan. With it, Falchi offered a new way of thinking about the handbag itself: although it was far from basic — some iterations had fringe and beading — he considered it an all-purpose, everyday accessory. — T.H.

Lopez: I mean, the simplicity. My mom had a fake version of it. It reminded me of, like, a thief’s bag from a different era.

Doonan: In the 1970s and early ’80s, the groovy customer didn’t have a bag and didn’t really seem to want one, and then this came along. There were obviously Chanel bags before this, but in terms of the customer who was buying Alaïa or Claude Montana, this was kind of the first.

Kim: How much were these?

Doonan: I think we’d be staggered if we saw the price. The idea that you could charge thousands of dollars for a bag hadn’t arrived yet.

21. Timberland’s Yellow Boot, 1973

In 1973, Nathan Swartz, the Odessa-born, New Hampshire-based owner of Timberland (which was called the Abington Shoe Company at the time), introduced a waterproof nubuck boot made by fusing leather uppers to rubber soles without stitching. Initially worn by construction workers, Timberlands, as they became known, soon transcended their rugged origins and were embraced, beginning in the late ’70s, by everyone from the Milanese jet set to British ravers. But it wasn’t until the ’90s, with the mainstream rise of R&B and hip-hop, that Timbs, as they subsequently became known, grew into a cultural phenomenon. Rappers like Tupac, the Notorious B.I.G. and members of the Wu-Tang Clan paired them with baggy pants; in 1994, Nas mentioned them on the track “The World Is Yours.” Soon, female artists including Aaliyah, Missy Elliott and Mary J. Blige were also wearing the clunky lace-ups, leading fashion at large to embrace the boots, too. Even Manolo Blahnik approved: In 2002, he released a high-heeled lace-up homage called the Oklamod. In a 2023 documentary celebrating the boot’s 50th anniversary, the New York rapper Rakim explained its appeal. “It’s more than just a boot, man,” he said. “It’s like a way of style.” — K.W.

Bradley: I guess this is the most influential workwear boot.

Kim: Remember Jennifer Lopez in those shoes?

Bradley: Of course!

Kim: Not only has it been completely feminized with that Manolo homage, but it clearly influenced how hip-hop intersected with fashion.

22. Nike’s Air Jordan 1 Basketball Shoe, 1985

It wouldn’t be an exaggeration to say that modern sneaker culture was born on April 1, 1985: the day Nike released the Air Jordan 1. Created as part of a five-year, $2.5 million endorsement deal with Michael Jordan, then a 21-year-old Chicago Bulls rookie, the shoe was designed by the Nike creative director Peter Moore, with innovative details including a padded ankle collar and fixed straps on the forefoot for extra stability. Its name alluded to both Jordan’s dunking skills and the high-tech pocket of compressed air added to the sole to cushion impact. Its bold black-and-red colorway violated the NBA’s dress code, which at the time required footwear to be 51 percent white, and the league fined the Bulls $1,000 the first time Jordan wore them on the court — threatening the team with greater fines and additional penalties should he wear them again — which only made them more covetable. Nike expected to sell 100,000 pairs in the shoe’s first year; instead, it shipped 1.5 million in the first six weeks. Although the Air Jordan 1 wasn’t the first sneaker created for a basketball player — Walt Frazier-branded Pumas and Adidas shoes with Kareem Abdul-Jabbar’s likeness on the tongue both came out in the ’70s — the deal between Nike and Jordan, in which Jordan received royalties on every sale, was revolutionary. — K.W.

Kim: He was sponsored by not only fashion brands but also Gatorade [and Coke]. It became such a status symbol. I remember going to the Fulton Mall [in Downtown Brooklyn] as a kid and loving these shoes — they didn’t come in girls’ sizes, but it didn’t matter.

James: And him being a Black businessperson, I just think it’s really special.

From python boots for Rudolf Nureyev to ankle-strapped pumps for Tim Curry in “The Rocky Horror Picture Show” (1975), Terry de Havilland made some of the most rock ’n’ roll footwear of the 1970s — he once told the Guardian that he’d “designed most of my shoes on acid.” At age 5, the British cobbler started working in his parents’ shop, Waverley Shoes, which catered to West End ladies in the postwar era. In 1960, after a brief spell as an actor (around which time he changed his name from Terrence Higgins), de Havilland, then 22, officially joined the family business and began reinventing his father’s 1940s platform styles in iridescent snakeskin. While platform shoes have been around since the 1930s, de Havilland’s psychedelic, five-inch-tall versions were especially popular during the glam rock era. In 2004, a BBC documentary revealed that Miu Miu had produced a near exact copy of his signature style. (The Italian brand reportedly agreed to pay him a settlement.) “I think they empower women,” de Havilland, who died in 2019, told T about his shoes. “They give you your own little stage to stand on.” — K.W.

Doonan: I’m going to demand that these Terry de Havillands get a spot, and I’ll tell you why. The Woodstock generation with its hippie style — a lot of it’s very influential now, but it was very earnest. What’s funny about Birkenstocks is how serious they are. Cut to 1972: [David Bowie’s] Ziggy Stardust album is released. It’s the birth of glam rock. Everything suddenly took on a shimmering, theatrical feel that was playful and camp. And what were girls going to wear with their satin hot pants? Not only are these platform shoes, which is a nod to the 1940s, but they’re snakeskin, which is so decadent and glamorous. To today’s eyes, they probably don’t seem like that big a deal, but oh my God, it was so brash and tarty and fun.

Bradley: When I see this shape, I picture Diana Ross boogieing. And then it was replicated by Miu Miu, Fendi and even [Christian] Louboutin. I feel like this is what women still wear with their bridesmaid dresses.

24. Launer’s Jubilee Bag, 1972

Over the course of her seven-decade reign, Queen Elizabeth II of Britain was known for her strict uniform: brightly colored dresses and coats accessorized with a three-strand pearl necklace, a jeweled brooch, block-heeled shoes and a variety of custom box-shaped bags with top handles from the British leather-goods maker Launer. Founded in 1941 by Sam Launer and owned since 1981 by Gerald Bodmer, the West Midlands-based brand was awarded a royal warrant in 1968 — which meant having permission to display the royal arms on its products — but its history with the House of Windsor dates to the 1950s, when, legend has it, the Queen Mother first acquired a Launer purse and gave one to her daughter. From the ’60s on, whether it was the Eleanor bag, made specially for the royal wedding of Prince William to Catherine Middleton in 2011, or the Jubilee, a popular 1972 style reintroduced in 2022 to celebrate the queen’s Platinum Jubilee, Queen Elizabeth II was rarely seen without one tucked under her arm — much to the reported dismay of Sir Hardy Amies, one of her longtime dressmakers, who felt it ruined the flow of his garments. Formal and structured, with a gold clasp in the shape of the brand’s emblem, a twisted rope, the bag epitomized the queen’s practical approach to fashion: She occasionally commissioned bespoke touches like a coin purse and longer handles for easier handshaking. She’s also rumored to have used the bag as a secret signaling device; according to the royal historian Hugo Vickers, she’d switch it from her left arm to her right to indicate that she’d grown tired of a conversation. — K.W.

Doonan: Respectable women wanted to look like this. Then the cultural revolution of the 1960s was about not having a bag. Everyone I know used to drag up and imitate the queen back in the day — it was a whole thing. All you had to do was buy a cheap white purse.

Bradley: My grandmother carried one like this to church. It’s like an Easter purse to me. You wear this with a pastel suit.

Doonan: We underestimate how important it was to project respectability in a chaotic world. The queen represented that.

25. Christian Louboutin’s Daffodile Heel, 2011

In the early 2010s, tabloids were constantly publishing stories about famous women’s bodies — who’d gained weight, who’d lost it and how. So perhaps it was no accident that Christian Louboutin’s Daffodiles became the celebrity shoe of choice: The six-and-a-half-inch platform heels, which came out in 2011, lengthened the legs and lifted the backside. Like a luxury version of the stripper’s Pleaser, they were a sexy rebuttal to the more ladylike single-sole stiletto. Daffodiles came in many styles and colors, including bright pinks and greens, leopard and graffiti motifs and Mary Janes and boots. Beyoncé sat courtside at the 2011 NBA All-Star Game in skinny jeans and a bedazzled version; Kim Kardashian said in 2017 that she had been “obsessed with them.” In 2011, Louboutin noted that he considers the entire body when designing a shoe. “When a woman buys a pair of shoes, she never looks at the shoe,” he said. “She stands up and looks in the mirror, she looks at the breast, the ass, from the front, from the side, blah blah blah. If she likes herself, then she considers the shoe.” — T.H.

Bradley: This was a game changer for a lot of women. You couldn’t escape it between 2010 to … Well, even now I sometimes see them in the Meatpacking District.

Doonan: Prior to this, a short heel was quite normal, but then we entered an era where no pornographic heel was high enough.

Kim: There are so many hip-hop songs about these red bottoms. I think he’s sued people over the trademark red too. But in that way, it also transcended cultures. I think Raul was saying something similar about the Balenciaga shoe: This one appealed to rich women, from the Real Housewives of Beverly Hills to basketball wives. It made no difference if you were Black, Asian, white — everybody has wanted a red-bottom shoe at some point.

Doonan: Fashion can’t all be about quiet luxury. It needs swagger, too, and that’s what this is.