There’s a science to the seemingly laissez-faire act of sporting an oversize shirt. As someone who veers oversize in every clothing category, I’ve had my fair share of misses. Too oversize can read sloppy. Not big enough, and the entire look feels off in an impossible-to-identify way.

Throwing out any ideas of sizing is a good place to start. So is shopping in sections you might normally skip, namely the men’s section. Balance is great, but have you ever tried balloon trousers with a billowing top? It’s kind of brilliant, not too serious, and the antidote to tailored silhouette fatigue.

Mélanie Masarin, founder and CEO of Ghia, who happens to write a fantastic newsletter on fashion, among other things, votes that oversize should be defined as stolen from your boyfriend, not your dad. “I realize that at 32, that’s a funny thing to say as these two individuals are very likely to be the same height, but if the shirt is way too long and makes you look like a child, then it’s too big!”

Masarin uses oversize shirts to imbue an otherwise formal outfit with a little casualness. Sandwiching an oversize button-down between a top and jacket is a signature move of hers. So is adding a sequin skirt or metallic pants on the bottom half. And the founder suggests showing some skin, even if it’s just your wrists or ankles. “For instance, if worn with long and wide pants, I would tuck or leave open over a slim top,” she says. “If a little leg is showing, with a tapered cut pant or a short skirt, then I like to leave it long.” Shopping on eBay? Mélanie loves to search “Ralph Lauren button-ups” for that classic Americana feel. Size up, of course.

Given that I’m over six feet tall, my POV on what constitutes as oversize, isn’t, let’s say, universal. I decided to tap one of my oldest friends, a fellow FIT graduate, and a very chic dresser, for more advice. Whoever said everyone in PR wears black hasn’t met Danielle Triano of Autumn Communications. Her style leans neutral, but at roughly a foot shorter than me, she’s mastered the oversize shirt look with lots of insights for the petite crowd—starting with notes on necklines.

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.