9 Long Shorts Outfits That Will Ease You Into Summer

Sometimes the short shorts need a break.

Printed shorts outfit collage

Design by Tiana Crispino

Spring is an interesting season for dressing as the weather changes almost hourly. One moment you’re in tank tops and shorts, and the next, it’s sweater weather. During those in-between months before summer, we need attire that can be as versatile as the weather. Enter: Long shorts. 

While millennials may internally cringe at the thought of Bermuda or other long shorts, fear not. Longer shorts are trending and can be styled in many ways—you can try a tailored pair of long trouser shorts with a blazer or denim Bermuda shorts with a bold top. If you’re still on the fence about long shorts, here are nine versatile outfits to help you make the look your own. 

Classic Look With a Twist 

Black denim shorts outfit collage

Design by Tiana Crispino

You can never go wrong with an oversize button-down and a pair of jeans. Give the classic look a twist by switching those jeans with a pair of long black shorts. It's a look that's great for running errands or taking a work Zoom call.

Princess Di-Inspired 

Bike shorts outfit collage

Design by Tiana Crispino

With movies and TV shows like Spencer and The Crown, a new generation is learning what a style icon Princess Diana was. Bring one of her signature looks back with a longer pair of bike shorts, an oversize crewneck, and white sneakers.

Summer Whites

White shorts outfit collage

Design by Tiana Crispino

Keep your look crisp and clean with a monochrome white outfit. Relaxed fitted long shorts, a simple muscle tee, and a pair of white mules create a simple outfit that looks effortlessly chic. Perfect for a hot summer day to keep you looking cool.

Business Casual 

Blazer and long shorts outfit collage

Design by Tiana Crispino

When in doubt, throw a blazer on. A brightly colored pair of long tailored shorts and a unique blazer create the perfect casual work outfit. Add a matching purse to complete the look. It can also easily transition to the perfect date night look for a bit of glam.

Regency Ready 

Regency outfit collage

Design by Tiana Crispino

If you’ve been obsessed with Regency romances, take the royal look into the spring with a corset top and a pair of cut-off long shorts. Perfect for when you want the Bridgerton look, but don't want to melt in the heat with those long dresses.

Cottagecore Inspired 

Cottagecore outfit collage

Design by Tiana Crispino

Cottagecore brought long shorts back to popularity. Indulge in Instagram’s favorite trend with a gingham blouse, long high-waisted shorts, and some cute oxfords. Perfect for adding a touch of romance and whimsy on a warm spring day.

Vacation Vibes 

Printed shorts outfit collage

Design by Tiana Crispino

Warm weather and summer vacations are just around the corner, so get ready with some playful looks. Long shorts are an easy, versatile item to add to your suitcase as you can easily dress them up or down and fits almost any dress code. Pair a bold print short with a neutral bodysuit and sunglasses for a beach-ready look.

Going Out 

Paperbag shorts outfit collage

Design by Tiana Crispino

Need an outfit for a night out? Take a pair of high-waisted long shorts and pair them with a cute bralette and jewelry. An ideal outfit for going to an outdoor bar or just having fun with your friends.

Early Spring 

Sweater and jean shorts outfit collage

Design by Tiana Crispino

For days when the mornings are cold but the afternoons are warm, grab a cropped cardigan and a long pair of denim shorts. This simple but stylish outfit is ideal for running errands or relaxing.

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