Settling This Once And For All - What Kind Of Shoes Are You Supposed To Wear With Baggy Denim?

After more than a decade as the world's go-to jeans, skinnies are out, and baggier cuts are the trend of the moment. Just one question: what shoes are we wearing with them?

Part of what made skinny jeans so versatile was how they lent themselves to a variety of footwear options. From ballerina pumps and sandals to heels, and pretty much any type of boot, skinnies had our backs. The truth is, while baggy denim has presented many of us with a challenge, making the switch just takes some getting used to. Plus, it may come as a surprise to many that the shoes we've rocked with skinnies pair just as well with their roomier cousins. Of course, there are some more 2023-esque updates to be made here and there, but the point is, finding a new home for our hoofs doesn't need to be stressful. So, with that in mind, just what are we wearing with bigger jeans?


Sneakers are the easiest way to get started

As intimidating as the thought of styling baggy jeans may be, there's a super easy way in, using footwear you're likely to have in your closet, already. Enter, the sneaker, in all its varieties. 

Classic sneaker styles, like Supergas, Converse, or Adidas Stan Smiths fit with everything from shorts and a t-shirt to midi dresses. So, it's not exactly surprising that when it comes to baggy jeans, they're probably the most natural way to get in on the trend. As a bonus, classic sneakers are essentially the neutral of the shoe world. That means just about any top will do, from fitted to baggy, and accessories can range from pared back to out there. 


For those wanting to make more of a statement, there's also the sportier route. Go for full-on 90s dad vibes for a fun take on the trend, like Instagrammer Natalie Alysa. Or, if you're somewhere in the middle, between sporty and classic, follow Jessey Turney's lead and go for the happy medium, with a style like the Adidas Samba OG. Classic, sporty, retro, yet super current. The bottom line is, sneakers are your friend, with the baggy jeans trend.

Ballet flats are back with a bang

Baggy jeans aren't the only throwback trend we're seeing, of late. Far from it, we're in the midst of a ballet flat renaissance — and the great thing is, both trends pair well together. 

For a very 2023 take, square-toed flats (like those seen on Instagrammers Ceriseamusante and Agnes Wlodarek) are a great bet. However, if square toes and baggy jeans feel a little too edgy, there's also a super classic alternative. Round-toe flats are just as on-trend as their more angular counterparts and make for the perfect Princess Diana street style-esque look. Take cues from the late princess herself — or, for some more contemporary inspo, peruse television personality Morgan Stewart's Instagram. Above all, if the elegant aesthetic is more your speed, balance out the bulkiness of the jeans with a delicate top, like a cardigan or well-fitted button-down shirt, a la Instagrammer Katryna Ton


And, if neither square nor round-toe flats float your boat, there's also always the pointed option. Still on trend — and paired with a high-waisted pair of baggy jeans, a great way to create the illusion of super long legs. Why did ballet flats ever go out of style, again?  

Chunky sandals keep things fun

Depending on what you're comfortable with when it comes to toe-bearing shoe offerings, there's no reason why baggier jeans mean sticking to closed shoes. Au contraire, for anyone hoping for a breezier summer, baggy jeans are just part of what's about to make that a reality. As for the shoes, themselves, chunky sandals up the fun factor. 


Chunky sandals make for a playful, youthful look, so there's never been a better time to play around with them painted with crop tops and bold colors. Think blogger Karina Eliana Ixta, pairing baggy jeans and chunky sandals with Y2K hair clips, and a bright blue button-down cardigan. Having said that, it's also worth noting that there are no hard-and-fast rules, here. As seen on Chanidra and Emma Streams, with the right top and accessories, even chunky slides can be glammed up for a sleeker look. 

As for those still dipping their toes into the maximalist sandals trend, who might not be ready to commit just yet, chunky doesn't always mean full-out flatforms. Think Blake Swanner in Birkenstock-inspired black mules. Sleek, simple, chunky without going overboard — and paired with a black crop top, a standout look that's equal parts playful and sophisticated. 


... and when in doubt, reach for a heel

So, sneakers, ballet flats, and sandals all work with baggy jeans — but what happens when we introduce a little more height into the mix? As it happens, heels and roomy denim are a match made in fashion heaven. Plus, they happen to be a perfect way to take your baggy jeans look from day to night.


Similar to how pointed pumps paired with baggy jeans elongate the leg, a pair of pointed pumps takes a denim look into a decidedly chic territory. As seen on Naomi Boyer, it's also a great way to play up those classic 90s and Y2K vibes. Speaking of which, it probably goes without saying that kitten heels are welcome, here. These elevate your loose denim look while still giving you a comfortable option. Pump and slingback styles are also a fun way to try the trend (we're looking at you, Julia Kammerer).