Each year as summer rolls around, there are certain fashion rituals that must be maintained: Fish your sandals out of storage, plan your rotation of breezy dresses, and prepare for the annual return of the jean short. Some iteration of this cropped denim staple is en vogue every year, but wearing it can feel intimidating if you buy into society's ideas about "dressing for your age." In truth, you don't have to stop wearing jean shorts once you hit a certain age -- just ask Erin Stoll, personal stylist and creator of Style Thief Fashion.

"I always encourage women to not let their numbers (age and size especially!) determine what they can and cannot wear," she shares exclusively with Glam. "That goes for shorts in general, but especially with jean shorts." The biggest tip Stoll has when it comes to wearing jean shorts is reframing your perspective on them. "Jean shorts ... are jeans," the stylist confirms. "Everything you wear with jeans, you can wear with jean shorts." She adds that this includes all of your favorite denim pairings, whether that's casual white sneakers (they are, after all, the one shoe that works with every pair of jeans), a low-key tank top, or even a more elegant blouse.

"You can also wear jean shorts for a date night or any time you want to dress them up a bit," Stoll notes. "If your go-to going-out look is a silk tank, heels and jeans, wear that exact combo with denim shorts." Accessories like belts and jewelry can further elevate this piece until your jean shorts are date-night ready. But before you experiment with styling, it's important to find the right pair of denim shorts for you, and that starts with looking at the length. While you don't need to exclusively wear longer, Bermuda-style shorts as you get older, being comfortable in what you're wearing is the key to looking good at any age.