A higher neckline and thicker material are a great place to start, according to Triano. These factors take a shirt from accidental to architectural. She loves the details, particularly the shoulders. “You can easily adjust the length and draping with a belt, or tuck, so go for something that frames your body well around the neck and shoulder area,” she says. Try pairing an oversize shirt with mid-waisted boyfriend jeans, she adds, or belt a long one without pants.
D’Ara Nazaryan, artist and founder of Aris, only ever buttons one button. “Whether it’s at my neck or navel, I pick one and stick to it,” she says. She’s known to style a long powder-blue button down with baggy low-rise black jeans and vintage Prada kitten heels, or a cropped oversize shirt with basketball shorts and frilly socks, plus loafers. She suggests sticking with something crisp, simple, and boxy. As evidenced by her outfits, a plain button-down worn well can be an ideal canvas for creative expression.
Worried menswear would overpower her, D’Ara used to shy away. Now, she knows life’s too short not to wear what you want. “I’ve found that dressing for the male gaze can suck the originality out of a look real quick anyway,” she says. “I’ve found my own way to embrace it. The best looks aren’t always the most complex or loud ones. I love it when I see someone’s point of view radiate through what they choose to adorn themselves with.”
Olivia Villanti, founder of Chava Studio, knows fabric. It’s part of her clothing line’s calling card. And when it comes to oversized shirts, she’s also an expert. A great oversize shirt begins with fabric that moves with you, according to the pro.“Generally speaking, a beautiful shirting cotton can hold volume without overwhelming your frame,” she says. “It’ll also just fall in a much more flattering way, versus a lower quality cotton which can warp and bubble the more you wash and wear it.”
Villanti’s made-to-measure designs read as a love letter to the tomboyish dressers among us. Inverted back pleats, custom-fit sleeves, and shoulders adjusted for smaller frames are just the beginning. In fact, working with Olivia to create Chava pieces of my own has convinced me that the secret to an oversize shirt is custom tailoring. Refined details and fit transport a shirt from feeling just okay into the statement piece you reach for for investor dinners, late-night dates, and Fridays when you shut the laptop early to make a lap around the Whitney. And remember, in most cases, bigger is better.
When in doubt, try your tailor.
