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

Shop away.

Originally Published: 
Christian Vierig/Getty Images
Baggy jeans with strappy sandals in street style.

It wasn't so long ago that baggy jeans were people’s go-to denim pick. Winona Ryder wore them everywhere she went in the '90s. TLC changed fashion forever when they wore undone overalls to a press call. And Aaliyah was the queen of making baggy jeans look cool. But as fashion skewed towards the super-skinny jean, looser fits fell out of favor — that is, until recently. Despite its sartorial comeback though, roomier denim can still seem tricky to pull off. But there's a quick fix: you have to choose the right shoes to wear with baggy jeans. Frankly, it's not all that surprising because a pair of loose-fitted jeans is a bonafide look and ordinary footwear simply won't do. Suffice it to say, the boot or sneaker you pair with your bottoms matters even more than, say, with your everyday skinnies or straights.

Because baggy jeans no doubt will remain a trend for the fall/winter 2021 season and beyond, it's the perfect excuse to turn to your favorite influencers and street style trendsetters for ideas. Below you'll find 11 shoe styles to wear with your baggy jeans, all of which are not only effortlessly cool but also most likely already in your closet (joy!). If they're not, shop the coinciding picks to fill the gaps.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.


Preppy wardrobe items are trending, so there’s no better time to add a collegiate touch to your baggy jean look. Finish off your OOTD with a sweater in a bold, maximalist print. Or, opt for an equally baggy sweater for an oversized look.

Kitten Heels

Give a loose pair of denim pants a ladylike touch with a kitten heel. For the office, try out the style with a sleek slingback silhouette, and on the weekends, opt for a strappy sandal with the mini heel.

Square-Toe Silhouette

Couple your roomy low-slung jeans with square-toe sandals for a ‘90s-inspired ensemble. Add on a baguette bag and you have yourself a whole outfit influenced by the trendy decade.


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


This unfussy, simple shoe is 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.

Chunky Sneakers

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.

Cowboy Boots

Edward Berthelot/Getty Images Entertainment/Getty Images

Team your baggies with a pair of trendy cowboy boots for a Western-inspired look. To finish, consider a classic button-down, or take style cues from Bella Hadid and throw on a jean jacket for a full denim-on-denim ensemble.

Strappy Sandals

Christian Vierig/Getty Images

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

Pointy Boots

Give the western trend a go and wear baggy jeans with a pair of pointy-toe boots. The two look especially polished when styled with an oversized pullover layered over a crisp white shirt and some stacked necklaces.


If chunky sneakers (or dad sneakers, as some might say) aren't your thing, there are still plenty of stylish options available on the sneaker market. Try a pair of trainers that will give your baggy jeans a cool, laid-back vibe. If you're feeling especially adventurous, opt for a colorful version to add a stylish pop of excitement.


Perhaps the biggest concern you may have surrounding the baggy jeans trend is whether or not it will come across as sloppy. The quickest way to quell these anxieties is by choosing a pair of shoes that can quickly counteract that. A pair of pumps (slingback, low-heel, or otherwise) is a no-brainer choice to wear with slouchier jeans. Complement the two with a fitted blouse and a roomy bag for a trend-forward ensemble.

This article was originally published on