The Best Shoes To Wear With Baggy Jeans & How To Style Them

Dilemma solved.

by Laura Lajiness Kaupke and Anna Traver
Originally Published: 
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While looser denim fits fell out of favor in the mid-2010s, when silhouettes skewed toward super-skinnies and straight legs, slouchy designs are back in full force as Y2K fashion continues to guide dressing habits in 2023. A trip down memory lane will prove how appealing the look can be: Winona Ryder wore it everywhere she went in the ’90s. TLC changed fashion forever when they all slipped into undone overalls for a press call. And Aaliyah, of course, was the queen of making relaxed dungarees look cool. Another key to pulling off the style? Choosing the right shoes to wear with baggy jeans.

Keep in mind that roomy jeans are a bona fide look, so ordinary footwear simply won’t do. The right heeled sandal, for example, can make you look instantly taller in the bottoms while a flat shoe coupled with extra lengthy pants may drown your petite frame. (And this is why having a trusted tailor for hemming is so important!) Suffice it to say, whatever slides, boots, or sneakers you pair with your baggy bottoms matters even more than, say, with your everyday skinnies or straight-legs.

Scroll on for your guide to the best shoes for the job, from timeless styles like ballerina flats to a pair of chunky loafers.

Ballet Flats

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To achieve the popular coastal grandmother aesthetic, style your favorite baggy jeans with an elegant pair of ballet flats. Team the pairing with a neutral-colored oversized sweater, a cohesive accessory color (in this case, a matching black purse and sunglasses really elevates the look), and of course a fresh out of the salon blowout. (Hello, Carolyn Bessette-Kennedy vibes!)


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Preppy wardrobe items are on trend, so there’s no better time to add a collegiate touch to your outfit than right now. Finish off your OOTD with a bralette and blazer or opt for an oversized sweater come fall/winter.

Strappy Sandals

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Strappy sandals are definitely having a moment, so grab yourself a pair and style them with something slightly unexpected: slouchy denim. And if it’s too cold to go barefoot, accessorize with a sheer sock in an eye-grabbing pattern.



It may seem counterintuitive to pair something bulky with another bulky piece, but the two can add up to a very cool combination. Balance the look with a slimmer silhouette up top to give the ensemble an air of insouciance.



This unfussy, simple shoe is one of summer’s biggest trends and a great option for those who don’t feel like spending extra time on laces and straps. Pair your favorite comfy slides and baggy blues with a basic white tee and a tote bag for a no-frills weekend look.



Think of it as a closed-toe interpretation of the sock-and-sandal pairing — a combo that provides a casual, model-off-duty look that’s both cool and relaxed. (FYI, Gigi Hadid is a big fan of this vibe.) You can even make clogs the centerpiece of your outfit by opting for a pair in a fun, eye-catching color.

Kitten Heels

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Give oversized denim pants a ladylike touch with a kitten heel. For the office, try out a sleek mule or slingback silhouette, and on the weekends, opt for a strappy sandal with the mini heel.

Square-Toe Silhouette


Couple your roomy blues with square-toe sandals for a ’90s-inspired ensemble. Add on a baguette bag, and you have yourself a whole outfit influenced by the decade.

Cowboy Boots

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Team your baggy denim with a pair of cowboy boots for a Western-inspired look. To finish, consider a classic button-down shirt, or take style cues from Meghan Markle and throw on a denim shirt for a Canadian tux-inspired outfit.

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