6 Flattering Denim Shorts and How to Style Them

Ira T. Martin

If there’s one item that gets the most use throughout the summer months, it’s unquestionably a pair of denim shorts. The ultimate weekend staple, denim shorts are our go-to summer saviors—most often thrown on with a striped tee and sandals for an easy, effortless daytime look. But finding a pair of great-fitting and flattering denim shorts is not always an easy feat. Like most denim, it takes trial and error to procure a pair you feel comfortable in that suits your style and body type. Luckily we did some digging and discovered the most flattering silhouettes guaranteed to suit every taste. Plus, we turned to our favorite fashion muses for endless inspiration on how to keep them looking fresh and stylish for every summer occasion. Scroll below for our favorite denim short outfits.

Sometimes the simplest outfit formulas work best. Wear your casual mid-rise denim shorts with an easy loose-fitting sleeveless white shirt, and finish the look with a pop of red—a cool bandana around your neck or tied in your hair looks unquestionably chic.

Madewell The Perfect Jean Short ($70)

A flattering mid- to high-rise waist with a lightly frayed hem give these shorts a cool, lived-in look.

Madewell Bandana ($13)

A pop of red is always a great complement to denim.

Mango Sleeveless Shirt ($50)

A crisp white sleeveless shirt never fails to look chic with denim shorts.

Hat Attack Small Round Handle Bag ($105)

A neutral tote will ground your look.

Elegant pearls and sophisticated tweed add a luxe touch to distressed denim shorts.

Free People Makai Cutoff Jean Shorts ($68)

Frayed shorts exude a laid-back, lived-in look.

Zara Slide Sandals with Pearls ($60)

The easiest way to add an elegant touch to your denim shorts outfit.

Mango Pocket Tweed Jacket ($80)

Tweed jackets continue to be a fashion-girl favorite.

Mango Braided Design Bag ($42)

Elevate your look with a luxe woven leather handbag.

Crisp white denim shorts pair beautifully with classic nautical stripes. Perfect for summer weekends.

Madewell The Momjean Short in Tile White ($60)

Tuck all your summer tops into a cool high-waisted pair.

Boohoo Striped Cross Over Bardot Tee ($13)

From day to night in style.

Janessa Leone Klint Hat ($188)

A favorite amongst the Insta set.

Le Specs Rapture Cat-Eye Acetate Sunglasses ($60)

Guaranteed you’ll be wearing these chic shades all summer.

Denim paper-bag shorts that tie at the waist add interest to your ensemble and a flattering silhouette. Pair with a crisp white top and combat boots for a summer look with edge.

H&M Denim Paper Bag Shorts ($30)

H&M Ribbed Jersey Top ($13)

A ribbed texture makes every top look more expensive.

Dr. Martens 1460 8 Eye Boots ($150)

Add a cool-girl edge to your ensembles with white Dr. Martens.

Distressed denim looks altogether chic when paired with a longline blazer (preferably in white), a neutral tee, and luxurious accessories.

Madewell The Momjean Short in Jeffries Wash ($60)

The perfect weekend shorts.

Madewell Acetate Buckle Leather Belt ($29)

A tan belt adds polish to frayed denim.

Cinq a Sept Crepe Khloe Blazer ($395)

Offset the distressed denim with this sophisticated white blazer.

Topshop Core Blue Zip Top Pouch Clutch Bag ($20)

Chic for day and night.

Wear clean denim with pops of bright, bold color this summer.

Topshop Premium Blue Denim Mom Shorts ($51)

These have a comfortable stretch to them.

H&M Creped Chiffon Blouse ($18)

Now here’s how to make a summer statement.

Caterina Bertini Woven Bucket Bag ($121)

A warm-weather must.

H&M Sandals ($35)

Because who wants boring shoes?

ZeroUV Horned Rim Keyhole Horn Rimmed Sunglasses ($10)

Complete your outfit with pretty pink frames.

Add a romantic touch to your long shorts with a pretty milkmaid style blouse.

Agolde ’90s Distressed Denim Shorts ($138)

Nail this season’s bermuda shorts trend with these cool-girl Agolde pair.

Majorelle Waldorf Top ($158)

So pretty.

Free People Sant Antoni Slide ($58)

These will work with everything in your closet.

A timeless oversize button-down adds a chic French-girl touch to light-wash denim shorts. Tie your look together with a black leather belt.

Madewell Relaxed Denim Shorts in Dunwoody Wash ($70)

These have a great flattering fit.

H&M Narrow Belt ($6)

A sophisticated addition.

H&M Cotton Shirt ($25)

Easy and effortless.

The easiest way to add polish to denim shorts is with a chic blazer and sophisticated sandals.

Agolde 90s Shorts ($148)

Trendy meets comfy. 

Violeta by Mango Gingham Blazer ($91)

This will take you into fall in style.

Madewell Northside Vintage Tee ($16)

You can never have too many.

Mango Interwoven Cord Sandals ($91)

They’re on sale, friends!

Voluminous sleeves are trending this season and they happen to look seriously cool with a pair of high-waisted denim shorts.

Madewell High Waist Denim Shorts ($42)

Reformation Lua Top ($148)

This post was published at an earlier date and has since been updated.

Up next, shorts are the new skirts—see the proof and shop my favorite pairs.

This article originally appeared on Who What Wear

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