A higher neckline and thicker material are a good start, according to Triano. These factors ensure that a shirt goes from coincidental to architectural. She loves the details, especially the shoulders. “You can easily adjust the length and drape with a belt or pleat, so choose something that frames your body well around the neck and shoulders,” she says. Pair an oversized shirt with mid-rise boyfriend jeans, she adds, or wear a long belt without pants.
D’Ara Nazaryanartist and founder of Aris, only one button is pressed. “Whether it’s around my neck or belly button, I pick one and stick with it,” she says. She’s known for pairing a long, powder blue button-down with baggy, low-rise black jeans and vintage Prada kitten heels, or a cropped oversized shirt with basketball shorts and ruffled socks, plus loafers. She suggests sticking with something fresh, simple and boxy. As evidenced by her outfits, a plain, well-worn button-down can be an ideal canvas for creative expression.
D’Ara worried that men’s clothing would overwhelm her. Now she knows that life is too short not to wear what you want. “I’ve discovered that dressing for the male gaze can quickly suck the originality out of a look,” she says. “I have found my own way to embrace it. The best looks aren’t always the most complex or loud. I love it when I see someone’s point of view reflected in what he or she wants to adorn themselves with.”
Olivia Villantifounder of Chava Studio, knows substance. It is part of the calling card of her clothing line. And when it comes to oversized shirts, she’s an expert too. A great oversized shirt starts with fabric that moves with you, according to the professional. “In general, a nice cotton shirt can maintain volume without overloading your body,” she says. “It will also have a much more flattering fit, compared to lower quality cotton, which can warp and bunch the more you wash and wear it.”
Villanti’s custom designs read like a love letter to the tomboyish dressers among us. Inverted back pleats, tailored sleeves and shoulders adjusted for smaller frames are just the beginning. Collaborating with Olivia to create Chava pieces myself convinced me that the secret to an oversized shirt is tailoring. Refined details and fit ensure that a shirt doesn’t just feel good, but becomes a statement piece you reach for during investor dinners, late dates, and on Fridays when you shut down the laptop early to take a lap around the Whitney. And remember: in most cases, bigger is better.
If in doubt, try your tailor.
