9 Outfits That Flex the Versatility of Paperbag Shorts

Paperbag shorts don’t have the sexiest name, but these are one of the most versatile and classy summer styles for bottoms. Fitted at the waist and then flaring out in pleats (hence the name), these aren’t just any high-waisted shorts. Their design and structure creates a looser fit around the hips and thighs that naturally accentuates the waist while creating an hourglass silhouette. If you enjoy comfort in your clothes and like to accentuate your waist, then paperbag shorts should be your priority this summer.

Not only are these shorts naturally flattering, but they are ridiculously versatile in how they can be worn. Because they come in various fabrics, it’s very easy to dress these up or dress them down.

I love wearing paperbag shorts with simple and snug tops paired with wedges or sneakers, but everyone’s style is different. When thinking about how to work these into your wardrobe, consider line and silhouette. While the fabric and color of the shorts may change, the shape is the distinctive characteristic that remains the same. Try sleek tops that let the silhouette of the shorts get all the attention, or look to dramatic tops that add volume to your overall outfit.

Below, you’ll find nine outfits that flaunt the many ways you can style paperbag shorts, from elevated brunch to vintage-inspired.

Cruise Chic

When I think of cruise, I think of effortlessness and ease. This look is all about those cruise-inspired sentiments of chic and relaxation. Lulus' paperbag shorts stand out because of their stylish bow detail at the waist. Tuck a simple and flowy silk shirt under the shorts to create an elegant and comfortable outfit. Then, choose your favorite boat shoes, and wear a waterproof necklace that won’t tarnish from a day by the shore.

Laid Back at Brunch

About 50% of the reason we go to brunch is to hang out and catch up with our friends over good food. The other 50% is about dressing up and showing out. If you love a laid-back and classy brunch look, then pair your paperbag shorts with a button-up and elevated sandals. The Dali Raffia Wedge Sandal from Veronica Beard is made of a monochromatic deep brown raffia that’s perfect to wear all summer long, from brunch to the beach.

Comfy Neutrals

Exploring a new city? Running errands? This is a go-to outfit on summer days where you have a long list of things to do but want to look stylish. With the right crossbody, drawstring paperbag shorts, and a relaxed T-shirt, you’ll be ready to face anything while looking fashionable the entire time. Bonus points if you wear cool shades.

Cutout Galore

These super-high waisted shorts give the perfect opportunity to flaunt a cool top. Cutouts, which allow for the deconstructing of a garment, are going to be one of summer 2022’s biggest trends. Add flair to this outfit with a beautifully symmetric cutout top from LA-based LNA. Wear this with your favorite sneaker, like the classic Nike Huarache.

Refined and Elegant

These shorts get their elegance from well-structured pleats and belt details around the waist. Add to the overall geometry of the look with an origami-inspired bag that complements the lines of the shorts. Tie it all together with a simple top that lets the shorts and bag shine.

Casual in Denim

Go for the ultimate summer casual look with basic denim paperbag shorts and a mix of styles through other elements. Off-White's Vulcanized Low-Top Sneakers add a touch of streetwear inspiration that beautifully complement the cropped rugby top from Rowing Blazers, a clothing brand known for creating designs simultaneously inspired by streetwear and prep.

Vintage Inspired

It’s easy to dress up paperbag shorts with button-ups and flowy blouses, but the shorts style is also great to use in a retro-inspired look. These black acid wash denim paperbag shorts nail the vintage aesthetic. Pair them with some classic high-top Converse, which are a sneaker classic, and a graphic T-shirt to achieve the old-school look.

Denim Daze

Denim is one of the most versatile fabrics that’s in-season year round. It dips in and out of various trends, breathing endless life into every new style and shape it takes. Try an all-denim look this summer with bow-detail paperbag shorts, a crop top, and Birkenstock sandals.

Color Craze

After gray winter months, one of the most fun parts of summer is bringing color back into your clothes again. Paperbag shorts are easy to find in timeless neutrals, but if you’re feeling bold, try the bright colors. This color-craze look combines a patch shirt with lemon yellow shorts and equally bright wedges.