Yes, Baggy Jeans Are Still Trending—These 10 Shoes Make Them Peak Cool

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Collage of street style photos of women's baggy jeans outfits.
(Image credit: @thecarolinelin; @nlmarilyn; @sarahlouiseblythe)
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Hot take coming at you in three, two, one: Slouchy denim will always be superior to slim silhouettes in this household. Don't get me wrong; I'm not delusional enough to deny that some might still feel drawn to skinny jeans. However, despite all the evidence pointing to the return of cigarette-inspired jeans, you could not pay me to put on a pair at this point. In fact, you'll have to pry my baggy denim out of my cold, dead hands. Dramatic? Probably, but let me explain my perspective. Unlike other denim silhouettes, loose-fit, baggy jeans are among the few denim styles that are actually universally flattering for every body type. Let's be honest. Skinny jeans are harder to shop for and wear when you're curvier or petite or have sensory issues! Even if you don't share a deep disdain for slim-fitting denim, there's no denying how baggier shapes have been deeply ingrained in fashion history. The nostalgic denim silhouette can conjure some of the most iconic images from the '90s of stars such as Aaliyah, Cher, and even Beyoncé.

One could argue that those prolific moments in pop culture prove slouchy shapes' staying power alone, but that doesn't mean that their continued relevance doesn't come with some caveats—mainly the challenge of finding a way to prevent this denim silhouette from feeling, well, dated. After all, how do you style jeans that have been around for decades in a way that feels modern? The solution to styling slouchy denim in a contemporary way is quite simple: Start from the ground up. Ultimately, deciding what shoes to wear with your baggy jeans is half the battle of making this dated denim trend feel cool again. But what are the best shoes to wear with baggy jeans? Luckily for you, that's where my slight fixation comes in handy, as I've spent hours researching which shoe trends pair well with this denim silhouette. Ahead, you'll find 10 shoe-and-denim styling combos that are sure to dissuade you from ever believing the propaganda that skinnies are, in fact, better than baggy jeans.

Polished Oxfords + Baggy Jeans

A woman walking down the sidewalk in London wearing black oval sunglasses, silver hoops, a long herringbone black and gray coat over a white T-shirt and light wash baggy jeans styled with black oxfords and a black bowler bag.

(Image credit: @sobalera)

Styling notes: One of the most common hurdles the fashion crowd faces when styling baggier denim is the shape itself. The looser fit can come off as too casual or not chic enough for others. The best way to offset a slouchier denim silhouette is to pair it with polished footwear. While there are plenty of shoes you can wear with this denim, try starting with one of spring's biggest footwear trends: oxfords. Frankly, there's no better way to make baggy jeans feel a bit more buttoned up than by styling them with menswear-inspired separates and accessories.

Pointed-Toe Pumps + Baggy Jeans

A woman in London leaning against a concrete building rail outside wearing oversized two-tone sunglasses, a black leather bomber jacket layered over a white t-shirt styled with a baggy wide-leg jeans, a black belt, a black bowler bag, a black necklace, and black pointed heels.

(Image credit: @nlmarilyn)

Styling notes: Another hurdle that may keep some people from testing out slouchy denim? The fact that it can sometimes feel tomboy coded, which isn't everyone's cup of tea. After all, when you've grown accustomed to wearing formfitting jeans, a baggy shape isn't always going to make you feel beautiful. Trust me when I say that you'll be surprised by how a little height can beautifully balance the proportions of a baggier pair of jeans. While any pair of heels can soften this androgynous shape, pointed-toe pump in a neutral shade will elevate your slouchy denim even further.

Minimalist Loafers + Baggy Jeans

A woman standing in the middle of the street in London wearing oversize two-tone aviator sunglasses with a long black fur coat layered over a white T-shirt, baggy wide-leg jeans, black ruched loafers, and a black Bottega Veneta Andiamo Bag.

(Image credit: @sarahlouiseblythe)

Styling notes: When you don't want to wear anything remotely uncomfortable but still want to dress up your baggier denim, it's essential to pick a pair of shoes that lean a bit more formal—enter, minimalist loafers into the chat. This preppy footwear can make any pair of jeans look just as polished as pointed heels without the pain of walking in pumps. Of course, if you're worried that loafers will make this slouchy silhouette a little too relaxed, consider incorporating other fancier accessories to seal the deal.

Square-Toe Ankle Boots + Baggy Jeans

A woman crossing the sidewalk in New York city wearing a black headband, black rectangular sunglasses, silver earrings, a black turtleneck sweater, a brown belt, black baggy wide-leg jeans, black square toe ankle boots, and a black barrel-shaped bag.

(Image credit: @cassdimicco)

Styling notes: Besides prioritizing comfort, consider the climate when choosing a denim-and-shoe combo. The last thing you want in the wintertime is to get caught outside walking around in flat shoes with no traction and a pair of super-baggy jeans grazing the salt-covered sidewalks. The secret to avoiding this mishap lies in wearing the right shoes with your jeans, specifically square-toe ankle boots. While you really can't go wrong pairing any type of boots with baggy jeans, the benefit of these boots is that their height will keep the hemline of your jeans from getting dirty. Plus, you'll elevate even the slouchiest denim silhouette with the trend-forward square-toe boots.

Flat Sock Boots + Baggy Jeans

A woman standing outside in front of a building wearing black sunglasses with a black leather cape coat, white baggy wide-leg jeans, and black leather sock boots.

(Image credit: @indiraci)

Styling notes: For those winter days when it's far too frigid outside to be caught in any type of heeled footwear, it's important to have at least one pair of flat boots in the back of your closet that can be effortlessly paired with your baggy jeans—sock boots are up for that task. It may come as a surprise, but I've slowly seen this dated footwear trend make a comeback, making it the perfect way to make any pair of slouchy denim feel contemporary again. The sleek shape of these boots will subtly let everyone know you keep up with shoe trends while still being practical enough to walk around in the snow or rain in the winter.

Ballet Flats + Baggy Jeans

A woman drinking coffee standing on a sidewalk in New York City in front of a bike wearing a navy cardigan tied around the shoulder, a light blue button-down shirt layered over a white tank-top, a black belt, baggy wide-leg jeans, black Tabi ballet flats, and a black tote bag.

(Image credit: @thecarolinelin)

Styling notes: Like clockwork, there comes a point at the end of every winter (and even summer) when you suddenly cannot spend another second wearing the staples typically associated with that season. Sure, nothing beats pairing leggings with boots or a dress with sandals, but no one is immune to growing tired of their favorite pieces and outfit formulas. In those moments, it's imperative to have a few styling combos in one's back pocket to break out of their fashion-related rut, and ballet flats and baggy jeans will surely put a little pep in your step while transitioning your closet from one season to the next.

Retro Sneakers + Baggy Jeans

A woman standing on the sidewalk in front of a restaurant in London wearing a black funnel neck bomber jacket, black baggy wide leg jeans, a brown plaid flannel tied around the waist, a burgundy clutch bag, and white retro sneakers.

(Image credit: @monikh)

Styling notes: No matter the season, there will always be occasions that call for a laid-back look. Whether you're simply running errands or meeting friends, you'll want a styling combo that's equal parts comfy and cool. Enter baggy jeans and retro sneakers into the chat. Although you really can't go wrong with any type of denim for casual plans, there's something about a slouchy denim silhouette that screams "cool girl" without even trying. It's amplified when you add a pair of trendy sneakers featuring retro-inspired details. Think low-top silhouettes and supple suede finishes.

Boat Shoes + Baggy Jeans

A woman standing in front of a home entrance wearing a black leather jacket over a white tank top, baggy white jeans, white boat shoes, a black bowler bag, and brown sunglasses.

(Image credit: @anoukyve)

Styling notes: Although sneakers paired with jeans will always be a cool styling combo, sometimes you might want to rock the boat by selecting a more controversial pair of shoes that will make you stand out from the crowd. Boat shoes will do just that. Over the last few seasons, we've seen a tidal wave of luxury houses, including Miu Miu, Hermès, and Tory Burch, release boat shoes to some people's delight and others' chagrin. Love or hate them, there's no denying that boat shoes are among the few types of footwear that can evoke as many, if not more, strong sentiments as ultra-slouchy jeans—making the idea of pairing the two all the more interesting.

Strappy Sandals + Baggy Jeans

A woman standing on a sidewalk wearing a white t-shirt tucked into a pair of baggy jeans styled with a pair of strappy sandals and a brown bowler bag.

(Image credit: @iliridakrasniqi )

Styling notes: Not all denim-and-shoe combos are universal crowd-pleasers, but then again, few other combos can fluently speak to different fashion languages quite like strappy sandals and slouchy jeans. If there were ever a shoe-and-denim styling combo that was going to give Duolingo a run for its money, you better believe it would be this one. There's something incredibly striking about the juxtaposition of slinky sandals and a pair of oversize jeans because it draws attention to the denim's dramatic shape without being ostentatious. It's no wonder, then, that we've seen maximalists and minimalists use this tried-and-true styling combo to make this denim silhouette suit their lifestyles.

Flip-Flops + Baggy Jeans

A woman standing outside in front of a concrete wall wearing a navy blue tank top with baggy white wide-leg jeans, black flip-flops, black sunglasses, and a black large barrel bag.

(Image credit: @deborabrosa)

Styling notes: The final type of footwear the style set is wearing with their slouchy denim is flip-flops. Yes, really. It might seem like a surprising styling combo, but given the rise of sought-after designer thong sandals and seasonless outfit ideas, it's really not all that shocking. Flip-flops have reached a new level of popularity over the last few seasons in a way that's on par with relaxed jeans, so of course, people have found ways to wear them together. It's further proof that the best way to revitalize your dated baggy denim is to pair it with the pieces giving you life at the moment, even if that's a pair of jelly flip-flops.

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Jasmine Fox-Suliaman
Jasmine Fox-Suliaman
Freelance Fashion Editor

Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.