What Type Of Shoes Should You Wear With Flare Jeans? These Are The Most Stylish Options

It is time to come to terms with an unavoidable truth: Flared jeans, like many other once-outdated trends, are back with a vengeance in 2025. It feels like it was yesterday when many Millennials traded in their flares for skinny jeans during the latter's heightened popularity in the late 2000s and 2010s. Though many stores never stopped selling flared jeans, it was easy to walk past them without giving it a second thought. But with younger Gen-Zers making '90s and Y2K fashion trend again, and with Kendrick Lamar having a viral moment with the denim at the 2025 Super Bowl, the relaxed denim is officially on trend again.

Something that we have to give the flared jeans credit for it the fact that they provide a more comfortable fit compared their skinny counterparts. Plus, they are known for working well on different body types. That said, figuring out what shoes to wear with them can be a challenge. Opting for regular flats, loafers, and sneakers will result in the fabric dragging against the floor, causing your hems to become frayed and dirty.
Thankfully, when it comes to styling these trendy jeans, the possibilities are endless, especially when it comes to shoes.  

If the name Mudd rings any bells, you may just be a Millennial. Just like the flare jeans themselves, wedge sandals have found themselves thrust back into our consciousness. With the way flares elongate the legs, adding a few more inches with some cute wedge sandals will continue to accentuate the illusion, while still giving you some stability. Opting for a wooden style will make your look even more fashion-forward for spring. 

If you have been dreaming of your own "The Devil Wears Prada" style moment, look no further. Pointed-toe heels have been having a comeback in the 2020s. The shoes are great for adding a chic touch to the groovy denim style. While you can never go wrong with a classic black pair, you can easily elevate your look by sporting a style with beautiful patterns and colors that make you stand out. Best of all, there are so many styles to choose from: sling-backs, kitten heels, pumps and more!

You don't necessarily need to wear heels to make flare jeans work. Seeing a nice chunky sneaker pop out from under the wide hem can provide an aire of effortless style that makes those monotonous errands look like a fashion statement.

Though any shade could work, if you're wearing light denim for spring, it's best to stick with lighter shades. You can wear white sneakers with everything and they truly stand out while you are wearing your flared jeans.

Whether metallic, western, or suede, ankle boots will have you channeling your inner '90s and Y2K baddie. Though we love a style with a chunky heel, we still cannot get over the classic stiletto heel boot. It offers sophistication and height to further elongate your legs in your flares; keeping the fabric from dragging on the floor, while making you look like THAT girl. Next time you hit your favorite shoe store, consider reaching for a pair of ankle boots to add a little something extra to your flared jeans outfit.

Open-toe heels go with flared jeans like peanut butter and jelly: Both are good without the other, but when they get together, it truly creates something special. The contrast of the dressy, stappy heels and the relaxed hem makes an otherwise casual look appear even more stylish. These Ankis Black 2.5 inch Heels in deep black will really pop against a pair of light wash flares, making them ideal for a spring time brunch outfit. Add in a black PINKMSTYLE Stretchy Bodysuit and your favorite spring time jacket to complete the look.