12 Jean Shorts Outfits That Are Actually Super Chic

Why mess with a classic? The key to making this combination look as chic as possible is to choose a T-shirt with a fit that’s loose but not so oversized that it overwhelms your frame or drops below the hem of your shorts. Finish the look with sleek sneakers or sandals (save the platform soles or funky high-tops for another day) for a chic and easy ensemble.

Shop similar styles: Abercrombie & Fitch Curve Love '90s Jean Shorts ($59; $35); Parks Project Pocket T-Shirt ($40); Allbirds Tree Pipers Sneakers ($105)

Wearing multiple denim pieces at once can be somewhat tricky to pull off. But one foolproof method is to choose two completely different washes—i.e. bright white and medium blue or deep blue and sunwashed gray but not light blue and dark blue. Add a pop of color in there as well to further differentiate between your jacket and your shorts.

Shop similar styles: GAP Stride Jean Shorts ($60); Old Navy Relaxed Denim Jacket ($40; $30); Bandier Willow Tank Top ($48)

For really hot days, swap your beloved cotton tank top for a dressier silk cami to give your shorts a more elevated feel. (Cotton or linen is great for casual wear, but if you’re dressing to impress, a luxe fabric—that’s just as breathable—is the way to go.) Add in some minimalist accessories, like simple strappy sandals and a single chain necklace to keep things light but chic.

Shop similar styles: Agolde Parker Jean Shorts ($138); Banana Republic Silk Cami ($50; $27); Monica Vinader Alta Link Necklace ($625); Amazon Prime Saddle Bag ($40); Reformation Meena Sandals ($198)

Both raw-hem shorts and tie-dye prints are classic summer staples we love to wear. But if you want to look more Manhattan and less Woodstock, you absolutely can. Just stick with dark-wash denim that has minimal distressing (i.e., no holes, just a raw hem) and tie-dye pieces that aren’t your typical T-shirt. We’re talking silky button-downs, Polo shirts, puff-sleeve blouses or a simple fitted long-sleeve tee. Complete your look with a few bright pops of color by way of luxe-looking accessories.

Shop similar styles: J.Crew High-Rise Jean Shorts ($80); Raqual Allegra Simone Shirt ($295); Mark & Graham Crossbody Bag ($119); Franco Sarto Caven Sandals ($99; $74)

We’ve found Bermuda-length shorts (aka, those that hit right at the knee) look best when paired with dressier pieces, like crisp button-up shirts or silk blouses and sleek sandals or heels. In fact, wearing a heel, however small, can help make sure all that denim doesn’t make your legs look shorter, so be sure to break out the pointy-toe kitten heels or wedding guest sandals.

Shop similar styles: GAP Bermuda Jean Shorts ($60); & Other Stories Classic Cotton Shirt ($89); Vince Camuto Brelanie Heels ($99; $50)

The best way to make denim shorts feel truly posh is to opt for non-distressed denim in either a bright white or deep black wash and pair it with a nice blouse and simple sandals. Denim will always feel pretty casual, but in a neutral hue it can look much more elevated and therefor go better with the fancier tops in your wardrobe.

Shop similar styles: Reformation Alyssa Jean Shorts ($98); Lauren Ralph Lauren Gingham Blouse ($125; $95); Ganni Pillow Shoulder Bag ($295)

A lightweight linen or cotton blazer can be a great summer jacket alternative to heavier materials, like leather or more denim. (We think light neutral hues like beige or off-white work better than darker shades or vibrant patterns.) Also, be sure to choose a blazer with a looser fit and that hits somewhere between mid-hip and the hem of your shorts—any lower and it might look sloppy, and higher will likely throw your proportions totally out of whack.

Shop similar styles: American Eagle Stretch Mom Jean Shorts ($50; $45); Madewell Cotton Bandana ($15; $8); Susana Monaco Crop Top ($78); Madewell Breezewoven Larsen Blazer ($148; $100); Gorjana Lou Link Necklace ($125)

For those with petite frames or short torsos, tucking a white shirt into matching white jean shorts (or blue with blue, black with black, etc.) can help lengthen your proportions to make you appear taller.

Shop similar styles: Madewell Relaxed Jean Shorts ($78); Everlane The Relaxed Oxford Shirt($80); Tony Bianco Corso Sandals ($170)

A short, tight Daisy Duke-style silhouette may be a classic, but shorts featuring wider legs and longer hems are swiftly growing in popularity. Play around with different lengths that hit anywhere between mid-knee and mid-thigh to see what flatters your leg shape best. Then revel in the improved comfort by pairing them with an oversize Polo or Hawaiian shirt.

Shop similar styles: Rag & Bone Maya Jean Shorts ($195; $135); Tory Sport Piqué Heart Shirt ($138; $109); Rothys The Point Flats($145)

Think of this as a sort of upgrade on your favorite T-shirt-and-shorts combination. If you’re not one for a full tuck, you can always opt for a French tuck or even knotting the loose ends of your shirt at your waist.

Shop similar styles: Frame Rolled Hem Jean Shorts ($210); FARA Silk Shirt ($253); L’Academie Amiyah Belt ($98; $60)

Colorful denim is having a moment again and we find it’s actually easier to pull off green, pink or orange shorts than it is full-length jeans. And our favorite way to wear them is with more bright hues for a supremely summery effect.

Shop similar styles: One Teaspoon Rollers Jean Shorts ($108); Maeve Linen Button-Up Shirt ($98)

The official start of fall doesn’t automatically mean fall weather, so don’t put those shorts into storage just yet. Instead, style them with some backless loafers or ballet flats and a cropped jacket that hips right at your waistband for an outfit that feels autumnal but won’t have you overheating.

Shop similar styles: Reformation Cowboy Jean Shorts ($78); Eileen Fisher Organic Cotton Jacket ($198; $102): Athleta Midtown Shirt ($98); Coach Sienna Slide Loafers ($119)