What to Wear with High-Waisted Shorts

by Emily Tozer

What to Wear with High-Waisted Shorts

They’re back! Sit-at-the-bellybutton shorts, pants, and skirts are back in style, but just how do best wear high-waisted styles? We styled five of our favorite pairs of this season’s shorts so you’ll know how to wear this cute spring trend.

It was only a matter of time before high-waisted skirts and high-waisted pants gave way to good old high-waisted shorts. And they’ve caught on in a big way. Whether you’re looking for retro and striped, ripped and vintage, or cute and tailored, there’s a pair that will satisfy your style craving. Plus, high-waisted shorts flatter nearly any body type. They can hide a slightly squishy belly and even add the illusion of curves to women who are stick-straight. A word of caution, however: Don’t don high-waisted anything if you already have a short torso. It will only make it look shorter by chopping you nearly in half. But once you’ve found a pair you love, just how do you wear them? We styled five different pairs to answer the question. Now what are you waiting for?


1. Ideal for a summer cocktail party or casual bridal shower, high-waisted sequin shorts are a fun alternative in a sea of cute cocktail dresses. Pair them with a white silk blouse, similar-tone strappy sandals, and a couple of gold bracelets for an effortlessly dressed up look. They can also be dressed down with a simple T-shirt and fun flats.

2. Play up the nautical vibe of these navy-and-white retro high-waisted shorts with a red top and espadrille wedges. We love the painter stripes and button-accented hem. Grab a pair of aviators and you’ll be ready to set sail!

3. These high-waisted denim shorts are perfect for summer. The subtle washed print gives them just enough detail to be interesting without being hard to wear. Tuck in a cream lace tank, grab a woven cross-body bag, and slip on a pair of orange ankle booties for just the right pop of color.

4. Tailored high-waisted shorts are a spring fashion must-have. These black-and-white striped shorts are made from a thick fabric and have a great flared shape that makes them more professional than your average shorts. Wear them with a black blouse and blazer to work, or with a cute graphic T-shirt after hours. Add pops of red in accessories, like a statement necklace and chic wedges.

5. The detail on these brocade high-waisted shorts is to die for. You’ll love the woven fabric, blend of colors, and flattering pockets. Wear them with a silky tee in a rich royal blue, long gold necklace, and perforated loafers.