The Most Comfortable Shoes To Wear With Baggy Jeans

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Influencer and Instagram content creator Amaka Hamelijnck wearing baggy jeans from Closed Official w...

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 fix: the key to wearing baggy jeans is finding the best shoes to go with them. Frankly, it's not all that surprising because a pair of loose-fitted jeans is a bonafide look and an ordinary shoe simply won't do. Suffice it to say, the footwear you pair with them matters even more than, say, your everyday skinnies or straights.

Because baggy jeans are no doubt here to stay for 2021, 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 and thrive in all your baggy, loose-fitting glory.

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Hiking Boots

Baggy jeans and hiking boots might seem like a strange pairing if you aren’t out on the trails, but according to influencer Anaa Saber, it’s worth a try. Finish off the look with a crop top or fitted tee to balance out proportions.

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 mom 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 ultra-relaxed. You can even make clogs the centerpiece of your outfit by opting for a pair in a fun, eye-catching color.


This unfussy shoe is a great option for those who don’t feel like spending extra time on laces, straps, and such. 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 somehow the two add up to a very cool combination. Balance the duo with a slimmer silhouette up top to give the ensemble an air of insouciance.

Combat Boots

Team your baggies with of-the-moment combat boots for a streetwear-inspired look. To finish, consider a slim top tucked in and colorful accessories, like square-frame sunnies and statement earrings.

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: baggy jeans. If it's too cold to go barefoot, accessorize with a pretty sheer sock in an eye-grabbing pattern.

Pointy Boots

Give the western trend a go and wear the baggy jeans trend with a pair of pointy boots. The two look especially polished when worn 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. Instead, 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.


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.

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