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