How To Wear Jean Shorts At Any Age And Look Amazing

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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.

Investing in a pair of denim shorts that don't ride up as you walk will make all the difference in your confidence, Erin Stoll explains. "This will vary for everyone, but I find that a 4 to 5-inch inseam will clear that uncomfortable spot and make it easier to walk and have enough thigh coverage," she tells Glam exclusively, noting that the length of the inseam tends to be the most significant factor turning older women away from jean shorts. "I know the super short 2-inch inseam isn't doable for most of us."

Don't be afraid to shop around with different brands to find the most comfortable pair of shorts that also speak to your personal style. "Brands like Old Navy and Gap have several styles and lengths," Stoll reveals. "You can find any wash, too. Some will have raw hems and distressing, but you'll also find options with finished hems that will look more polished." A-line jean shorts are the perfect mix of comfort and style if you don't like ultra-tight shorts but also don't want them too baggy. Stoll advises against sticking exclusively to blue denim (unless, of course, that's what you feel comfortable with): "This season we're seeing jeans and jean shorts in black, white, prints and colorful denim ... " Meanwhile, the Bermuda silhouette is taking over 2025, and Stoll recommends pairing it with ultra-chic blazers and tailored button-downs. 

After you've bought your jean shorts (or brought them out of winter storage), Stoll advocates for wearing them around the house before you show them off to the world. "Seriously, it sounds strange, but it really helps [with the shock of wearing shorts for the first time after winter]," she says. "We have to just desensitize seeing parts of our bodies that have been covered up for months." Once you've accepted that you look amazing in your shorts, it's time to style them.

Jean shorts return with a vengeance every year because they can be worked into practically any outfit. Say you want to create a look that's a little dressier than your standard denim shorts and tank top combo. Erin Stoll suggests teaming up your shorts with a blazer. "I prefer the relaxed, slightly oversized blazers with denim shorts," she says. "The blazer adds polish and structure, but the relaxed silhouette combined with the shorts makes the whole outfit feel approachable."

By the same token, you can add pieces that are more feminine to your ensemble, as they'll soften the look. "Pair a floral blouse with jean shorts and a pair of metallic sandals," Stoll advises in our exclusive chat. If you want more of a casual look, consider tank tops, bodysuits, and open knit sweaters and shirts, or perhaps layer a few of those options. "Wear that combo with a pair of flats or woven sandals and your favorite summer bag," the stylist adds. "I also love a solid white or black tee with a black belt, slingbacks, and some jewelry for a classic, polished look." Stoll loves belts, in particular, for completing a denim-shorts look. Something simple, like the Glamorstar Skinny Belt, can make your outfit seem put together without stealing the show. You could reach for a bolder style if you lean toward more maximalist fashion or something with more prominent hardware, like the Risantry Black Belt with its ring-shaped gold buckle. And, if after all of that, you still don't think jean shorts are for you, then you might like to consider cropped denim, the jeans trend that's taking over summer 2025.