13 Shoes to Wear With Shorts

If you find yourself reaching for the same pair of bike shorts and sneakers, summer Friday after summer Friday, you've come to the right place. This year, steer clear of summer fashion fatigue by reinventing your go-to shorts outfits from the ground up, starting with our picks for the best and most fashion-forward shoes to wear with shorts.

Whether you're looking for the right pair of comfy, casual shoes for a laid-back vacay or hoping to level up your office-approved shorts outfit rotation, the 13 pairs of flats, boots, and heels ahead will have you counting down the days 'til the forecast calls for bare legs. Ahead, you'll find the perfect shoes to wear with every style of shorts, from tiny cut-offs to knee-crazing cargoes, plus tips on how to style them.

Ballet Flats

If you're going for an effortless, cool girl vibe, you can't go wrong with wearing ballet flats with shorts this summer. We recommend going minimal with this style of shoe to wear with shorts; a simple pair in black worn with slouchy crew socks feels most fresh.

Loafers

We recommend stepping into a pair of sleek and supple loafers for a quietly luxurious vibe. A somewhat unexpected choice, loafers are both trendy and timeless, making them an excellent choice for a casual but still elevated shorts outfit.

Platform Sandals

This one's for the fashion girlies who dare to wear socks with sandals. Platform sandals deliver comfort and style in equal measure. The extra inches on this shoe, worn with shorts, give the effect of a pair of sky-high stilettos minus the risk of losing your balance and create a "legs for days" look regardless of your actual height.

Sling-Backs

Slingbacks have been spotted up and down recent runways, and we love the vampy vibe they bring when worn with a chic shorts and suit combo. To level up this work-place-approved shoe and shorts pairing, choose a pair in a vivid spring shade and an eye-catching fabric like satin.

Sporty Sandals

Since chunky normcore sandals won't stop trending, we're working that energy into our summer shorts outfits. A pair of sporty hiking sandals worn with patterned shorts and a sharp blazer creates a conscious aesthetic clash that draws the eye.

Over-the-Knee Boots

Wearing over-the-knee boots with shorts is the ultimate fashion-forward power move. We recommend luxury separates, light colors, and timeless prints for daywear. The perfect 'fit for this style of shoe? A cashmere sweater, checked high-waisted shorts and cream-colored over-the-knee boots. 

Cowboy Boots

You don't have to be a proud worker bee in the Beyhive to know that cowboy boots will reign supreme as this summer's trending shoe of choice. Go full coastal cowgirl, or incorporate this classic boot style into your go-to shorts outfits by swapping them for your usual sneakers, flats, or sandals.

Classic Pumps

Whether worn subversively chic with denim cut-offs or elevated and upscale with paper bag shorts, classic pumps deserve a spot in your shorts outfit footwear rotation simply because they're so darn versatile. Worried about getting sweaty feet in a pair of leather heels? Embrace your inner street style star and add a pair of sheer statement socks.

Block Heels

Block heel sandals are another shoe to wear with shorts that deliver elegance and fashion-forward energy without sacrificing comfort. To ensure this pairing feels cohesive and intentional, we recommend taking the time to color-match your shoes to either your outerwear or accessories.

Oxfords

While menswear-inspired looks are more accessible to style in cooler temps that call for layers, you can still capture that vibe in warmer weather by wearing oxfords and a blazer with your favorite pair of slouchy shorts.

Combat Boots

Create a rugged, casual shorts outfit with hints of rock n' roll energy by wearing your favorite pair of combat boots with black denim shorts. A plain white t-shirt and oversized, lightweight jacket keep this look low-key, but you can amp it up with statement accessories.

Elevated Flip-Flops

No shade to flip-flops, but we prefer their more elevated, well-heeled cousin: the high-heel flip-flop. This style of shoe is ideal for adding considerable fashion energy to even the most casual of bike shorts outfits.

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