The Best Shoes to Wear With Baggy Jeans, Because This Denim Trend Isn't Going Anywhere


Lest you forget, it wasn't so long ago that baggy jeans were the go-to denim of top trendsetters. Winona Ryder wore them basically everywhere she went in the '90s. TLC changed fashion forever when they wore undone overalls to a press call. And of course, Aaliyah, the queen of making baggy jeans look cool, made every oversized denim outfit look, well, perfect. 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 simple 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 2019, it's the perfect excuse to turn to your favorite influencers and street style trendsetters for ideas. Below you'll find six 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.

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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2019 is most certainly going to be a good year for strappy sandals, so grab yourself a pair and style them with something slightly unexpected: baggy jeans. If it's too cold to go barefoot right now, 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 a blazer, lived-in white tee, and everyone's favorite everyday jewelry piece: the pendant necklace.



If chunky sneakers (or "dad sneakers" as some might say) aren't your thing there are still options. Instead, try a pair of trainers that will give your baggy jeans a cool, laidback vibe. If you're feeling especially adventurous, opt for a colorful version to add a stylish pop.



Perhaps the biggest fear 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 mini bag for a trend-forward ensemble.