A little black dress and heels, a tee and jeans, shorts and sandals…some combos will always be classic, but that doesn’t mean they can’t occasionally feel a little stale and uninspiring. Now that we’re in the heart of summer and inching toward fall, we’re taking a moment to focus on the latter—and turn that narrative on its head.
The trick to making shorts and sandals feel fresh again comes down to two no-fail approaches: reinventing the familiar with cool colourblocking, an interesting silhouette, or striking textures (of course, flip-flop heels have been cropping up in some of the coolest au courant outfits lately), or centering a look around a bold choice (animal prints and vibrant patterns are certainly not off the table this season). From celebrities like Hailey Bieber to the stylish attendees at this month’s Copenhagen Fashion Week, the looks we unearthed below highlight just how nuanced—and nearly endless—the possibilities are.
Without further ado, here are nine inventive ways to style sandals with shorts that you’ll want to wear on repeat in the coming months.
Brown Heeled Mules and Bermudas
For a switch-up from black, try an equally versatile brown heeled mule that can be styled with practically everything in your closet. The silhouette is perfect for elongating the look of some oversized cotton Bermudas and a rugged plaid button-down—an ensemble that’s even office-appropriate.
Subtle Animal Print Infusion
Animal-print shoes have been everywhere this season and show no signs of disappearing this fall. À la Monica Barbaro, keep things simple yet sophisticated with a subtle flip-flop heel, paired with a silky brown button-down (expertly cuffed at the elbow) and tailored black shorts.
Track Shorts and Peep-Toe Sandals
Ruched and gathered shoe styles are also quietly sliding into the spotlight. Saint Laurent’s Hailey Bieber-approved Babylone peep-toe mules, famously sported by the star last September, are a prime example. A cropped white tee and trendy athletic shorts keep things comfy and laid-back, while an oversized leather bomber jacket adds an extra layer of warmth as temperatures drop.
Mood-Boosting Hues
In line with the resurgence of serotonin-fueling shoe styles, what could be more fun than a splashy rainbow-print block heel or printed wedge sandal? Today’s interpretations, like Larroudé’s multicoloured raffia platform sandals, read less kitschy and juvenile and more elevated and whimsical—especially when coordinated with a pair of silky cobalt-blue shorts and a petite fuchsia shoulder bag. Keep the palette neutral up top with a white crewneck tank and light-wash barn jacket, save for a few accessories, if you so desire, like a colorful pendant necklace and slim tinted sunglasses.
A Brown and Gray Medley
Here’s further evidence that brown sandals and grey pieces work beautifully together. A faded denim groutfit feels effortlessly cool, while chocolate-brown flip-flops and a matching handbag soften the look in the best way.
The Lazy Girl Hack
We all know and love the timeless black leather flip-flop heel, but have you tried pairing yours with longline sweat shorts and a blazer? Keep it unbuttoned with a bralette peeking out from underneath for a sultry spin, and add a gold herringbone necklace to keep the look from veering too casual.
The Black and White Palette
Already inherently sleek and elegant, a black barely-there T-strap somehow feels even more refined paired with pleated white shorts and a matching off-the-shoulder knit top. A slim black belt, classic Ray-Bans, and interlocking hoop earrings only add to its Hamptons, CBK-coded appeal.
Butter Yellow Flip-Flops and a Chestnut Suede Set
Also worth filing under interesting color combos: butter yellow, chestnut brown, and a touch of blue. A padded pair of flip-flops in the sunny hue along with a matching tote—styled with an unexpected suede short set and a jewel-toned silk scarf tied around the waist—can easily become one of the most eye-catching everyday fits in your transitional and early-fall wardrobe.
Red, White, and Black
Another fashion insider-approved way to style your black flip-flop heels is with crisp white denim Bermuda shorts and a punchy red jacket—a trio that might just become one of the buzziest looks this autumn. While viral versions like Polo Ralph Lauren’s Dua Lipa-worn track jacket and Hailey Bieber x Mango’s style are now sold out, we’re seeing retailers like Zara drop equally covetable styles you can still get your hands on.
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