Denim Shorts
12 Ways to Dress Up Denim Shorts This Summer

Style Your Jean Shorts to Look Classy

Denim shorts are a summertime go-to for the beach and backyard — but you may not know how to dress up this warm weather staple. We’re here to show you that jean shorts can look classy enough for dates, shopping with friends and even some offices. Don’t believe us? Browse our gallery of dressed-up denim shorts outfits and get inspired to wear your cut-offs in new and fashionable ways this year.

Wear Jean Shorts and a Bomber Jacket

Wear Jean Shorts
Layer a go-to bomber jacket over your jean shorts this summer.

Here’s a look you can wear everywhere on casual days this summer, from lunch and shopping to taking the kids to camp. Simply layer a lightweight, hip-length bomber-style jacket over a simple tee and cut-off jean shorts, such as this classic, dark wash pair from Joe’s Jeans. Add a hobo-style bag and fashionable sandals in neutral tones for effortless chic. An aqua scarf with a biker motif is a cool addition.

Colorful Summer Outfit in Jean Shorts

Colorful Summer Outfit
Create a colorful palette to dress up jean shorts.

Are you a woman who loves what wearing color does for her complexion? Here’s how to create a bright, colorful summer outfit that looks stylish and fun, without veering into clown territory. Start with distressed denim shorts, such as the denim short pictured here by Dsquared2. Then bring in the color with a red short sleeve blouse and a medium-blue summer blazer. Add a blue statement necklace to pull the pieces together and finish your outfit with leg-lengthening nude high heel shoes.

Date Outfit with Denim Shorts

Date Outfit with Denim Shorts
Date Outfit with Denim Shorts. Photo Credit: Levi’s

Here’s how to wear denim shorts on a date and still look dressed up enough for cocktails and beyond. The trick here is staying covered on top, so the focus is on your legs and adding expensive-looking accessories to glam things up. You’ll never go wrong with a black-and-gold color palette. Kick-off your outfit with a pair of classic, cuffed denim shorts, such as this lightly-distressed pair from Levi’s.

Match them with a silky, long-sleeved blacktop, then add fierce black heeled sandals and a gold-tone clutch purse and jewelry. Wearing sunglasses? Choose golden-toned frames to complement your other accents.

Black and Blue Outfit with Denim Shorts

Black and Blue Outfit with Denim Shorts
Black and Blue Outfit with Denim Shorts. Photo Credit: Topshop

Mixing black and blue in your outfit gives you an instant update. Take on this trendy and easy-to-wear color palette in a dressed-up denim shorts outfit that’s perfect for city strolls or shopping. Pair high-waisted denim shorts, such as these from retailer Topshop, with a sleeveless black blouse, then layer a perfect-fitting navy blazer on top. Flip-up the cuffs of both the shorts and jacket for a fashionable touch.

Menswear-inspired flat shoes, a gold pendant necklace, and colorful sunglasses complete this effortlessly chic look.

Get more fashionable inspiration for wearing black and blue together.

Hipster Outfit with Denim Shorts and Hat

Hipster Outfit with Denim Shorts
Hipster Outfit with Denim Shorts and Hat. Photo Credit: Levi’s

Want to look trendy and fashionable in denim shorts, while still keeping your vibe young? Instead of your usual tank top, try wearing a sleeveless black blouse untucked over frayed-hem denim shorts (these are Levi’s). Then add funky accessories that give you tons of style, such as a straw fedora (also doubles as sunscreen), statement earrings, and sunglasses in a funky pattern. Finish your outfit with a chain-strap purse and notice-me sandals — we love this detailed shoe from House of Harlow.

Linen Blazer with Denim Shorts

Linen Blazer with Denim Shorts
Linen Blazer with Denim Shorts. Photo Credit: Chloe

Most offices don’t welcome denim shorts — but this ensemble might change some minds. You could certainly wear this chic denim shorts outfit and look dressed up for shopping, gallery-hopping, or lunch with friends. Pair denim shorts with a classic white shirt (tucked-in) and top with a fitted white blazer. Look for a jacket with structured shoulders that nips in at the waist, such as the one pictured here by Chloe, for a slimming effect.

Then add high-quality, lady-like accessories that take your look to the next level and give your shorts outfit a distinctly grown-up feel.

Kimono Top and Denim Shorts

Sometimes, fashion magic can happen when you mix together unexpected items. We love the surprise factor of a silky, dressed-up kimono-style top when worn with denim shorts. A patterned kimono can make your bohemian style clothes perfect for backyard parties and cottage weekends with your favorite jean cut-offs. Keep accessories simple and bright, such as the cobalt sandals and Milly bag pictured here.

Edgy Date Night Outfit in Denim Shorts and a Blazer

Edgy Date Night Outfit
A tuxedo jacket looks cool over distressed jean shorts. Photo Credit: DSquared2

Do you want to keep cool for summer, while maintaining your edgy, confident vibe? You can’t go wrong in this stylish outfit of distressed denim cut-offs (these are by DSquared2), paired with a perfect-fitting black blazer. Wear with chunky ankle boots for a stand-out look.

White Top and Denim Shorts Outfit

Denim Shorts Outfit
White Top and Denim Shorts Outfit. Photo Credit: Topshop

You already know that denim shorts and a white top are a classic fashion combination. Rather than pulling on the same old white t-shirt, though, why not try something a little more grown-up? You’ll look stylish — not student-like — when you match denim shorts with a lady-like white blouse, such as this bib-front style by Topshop. Then edge things up with toeless ankle boots, a bright clutch, and earrings for a pop of color.

White sunglasses are trendy and help draw attention upward on your body, which helps balance your look in shorts.

Striped Shirt and Denim Shorts

Striped Shirt and Denim Shorts
Striped Shirt and Denim Shorts. Photo Credit: Citizens of Humanity

If you’re a preppy at heart, here’s a go-to summer look that’s classic, cool, and stylish. Start with classic jean shorts, such as this Ava style by the Citizens of Humanity brand. Then add a crisp, striped button-down shirt, doing the buttons upright to the top. (You can tuck in the blouse or not, depending on your mood and style). Pull your outfit together by layering a major statement necklace in blue over your shirt.

A red clutch adds another welcome pop of color, while nude shoes help elongate your leg line right down to toes.

Summer Outfit with Leopard Print and Denim Shorts

Leopard Print and Denim Shorts
Summer Outfit with Leopard Print and Denim Shorts. Photo Credit: H&M

Here’s an easy, sexy outfit that’s perfect for lounging at a beach-side patio, or walking with a date on a warm summer day or evening. Start with comfortable white denim shorts, such as this classic pair from H&M. Layer on an exotic leopard-print blouse (pop a camisole underneath if it’s too sheer), then add one big gold-tone accessory — our choice is a cuff bracelet. Aviator sunglasses and chunky-heeled sandals are summer classics that keep this look effortlessly cool.

City Outfit With Distressed Shorts and a Moto Jacket

City Outfit With Distressed Shorts
Strike a cool pose in a moto jacket and ripped jean shorts. Photo Credit: Current/Elliott

You don’t have to retire your trendy leather jacket in the warmer months. A moto-style jacket looks edgy and unexpected when layered over distressed jean shorts (these are from the Current Elliott brand) and a basic tee-shirt. This is a great outfit to wear shopping in the city, on a date, or meeting the girls for cocktails on summer evenings. Wear high-heeled black sandals with this outfit to dress it up and lengthen the look of legs.

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