4 Stylists Answer All Your Shorts Questions
Skwad Photography / BLAUBLUT EDITION
With spring’s slow (and stubborn) approach, the promise of lighter dressing is right on the horizon. After a brutal winter, we’re ready to free our legs from wool trousers and oppressive boots. Calves, meet fresh air! It’s been awhile. That said, though we’re gleefully stocking up on skirts and sandals, shorts—always tricky to style—inspire a bit more trepidation: How to choose the right pair? How to style them? On matters of length, proportion, and material, we have questions. Luckily our Rolodex is full of women who solve fashion riddles all day. We turned to four of them—the stylists Dione Davis, Laura Stoloff, Alexis Badiyi, and Patricia Lagmay—for answers to our most pressing queries.
How do you decide on the right shorts length?
There’s no single rule, but proportion and personal comfort are key. Davis emphasizes that “whatever length feels comfortable” is the right starting point, though she’s especially drawn to longer Bermuda shorts for their ability to balance more-feminine pieces. Stoloff agrees: “I find that both tall and petite body types can wear long and short lengths. It's more about how they are tailored and the width of the shorts.”
Badiyi frames it in terms of proportion. “Shorts are not a one-length-fits-all category,” she says. You want to focus on where shorts hit the leg and the height of the shoe they’re paired with. “Ultimately, you don’t want a pair of shorts to shorten your silhouette or create an optical illusion that works against you,” she explains. Lagmay notes that the width of the leg opening matters just as much as the length: “Openings that are super tight and slim to the circumference of your leg are always tricky because it will feel like your legs can't breathe and move. Whereas something with a slightly wider opening is more flattering.”
How do you choose the right shorts for your body type?
“People should wear whatever length they want as long as it’s appropriate for the setting they are going to,” says Davis. Stoloff agrees: “It’s more about style preference,” she says, though she recommends more-tailored styles for petites. “If you’re taller, you can opt for an oversize look.”
Are there any universally flattering styles?
Not exactly. While Stoloff points to a mid-thigh or slightly longer tailored short as a reliable option, the idea of universality is elusive. “It depends on comfort and body type,” says Lagmay. The least flattering style? “Short shorts with a cuff,” according to Davis. “That’s a great way to look like a potato.”
How do you approach shoe pairing?
All four women agree that shoes set the tone. Badiyi follows a simple formula: “The shorter the short, the lower the heel. The longer the short, the higher the heel. Adding a bit of lift to longer styles can help elongate the leg line.” Davis agrees: “Short shorts with a tall heel are generally not my favorite. A kitten heel and a 2.5 inch are the only acceptable options—otherwise you look like the girl at college night at the bar.”
Lagmay tends toward ease. “I really only wear loafers, flats, or flip-flops,” she says, especially when balancing looser silhouettes up top.
How would you style culottes?
“Culottes can be particularly tricky,” says Badiyi. “They often create an optical shortening effect if the proportions aren’t considered carefully.” She gravitates toward pairs that sit lower on the waist, with a relaxed, natural leg. “To offset the volume, I keep the top more fitted,” she says. “And footwear is key. I’ll almost always pair culottes with a heeled sandal or mule to add height and maintain a sense of lift.”
Stoloff echoes this sentiment. “Since culottes can feel heavy and sometimes have an awkward length, I recommend pairing them with light shoes,” she explains, “I would also pair them with a simple top—a T-shirt, knit, or button-down—with clean lines.”
How can you make shorts feel more refined?
A few strategic tweaks make all the difference. Davis suggests belting them for structure, while Stoloff leans into longer, tailored styles styled with button-downs or blazers. “I love a short suit,” she says.
What materials work best?
Natural fabrics are the clear winner here. Davis suggests linen, cotton, and tropical wool, and Stoloff avoids synthetics altogether. “I don’t like how they feel, especially in the heat,” she says. Lagmay prefers poplin and tends to steer clear of linen due to its tendency to wrinkle, “with a garment that small, it’s hard to get away with.”
What would you say to someone who thinks they can’t wear shorts?
“You can wear whatever you want if you have the right foundational pieces to support it,” says Davis. Stoloff echoes that it’s all about tailoring and fit. And Lagmay offers the most succinct advice: If your hesitation stems from perceived rules, “maybe just say f*ck ’em.”
Wear Them With
