What Shoes Can You Wear With Flare And Bootcut Jeans?

Millennials, I think we can all admit that skinny jeans have had us in an absolute chokehold for the last 10 years. So now that flare and bootcut jeans are showing up more and more in our Instagram feeds and in stores, it can feel a little foreign when you get them home and put them on. Styling them can feel especially complicated when it comes to one thing: shoes.
If you used to rock flared jeans back in the day, you know exactly how they look with crusty old Converse or metallic gladiator sandals (and chances are you’re not trying to re-create that aesthetic). But what shoes should you wear with flare and bootcut jeans?
First things first: You don’t actually need different shoes for skinny jeans and flares. Your old faves may just look off because you’re not used to seeing them with pants of this style.
“I often get told by people that they don’t like the way that wide-leg pants or flares or bootcuts look on them initially,” said Cate Kittlitz, a content creator and fashion influencer. “And my first response is always like, ‘How long have you tried them for? Was it just throwing them on in a changing room?’ It does take your eyes some time to adjust to the new silhouette, especially after wearing skinny jeans for so many years.”
Once you’ve given yourself some time to get used to the look of flares — and the sudden draft around your ankles — Marie Denee, a plus-size fashion and style blogger and creator and founder of The Curvy Fashionista, recommends pairing flares with something pointy.
“If you are more hippy, more pear-shaped, or if you carry most of your weight down in your booty and your thighs, a bootcut’s going to give a fun little balance. It’s a visual thing. And so, when it comes to the shoes, you want to keep that line, you want to keep it going, and that is what a pointed-toe shoe allows.”
Kittlitz said if you’re totally lost on what footwear works with flares that the best rule of thumb is to create balance.
“With wide-leg pants in general, a narrow shoe is going to pair really nicely because it’s creating that balance,” she said. “Just like if you’re wearing like a really, really slim-legged pant, going for a chunkier shoe is going to create balance. Especially since skinny jeans are often paired with ballet flats or something very slim as well, we’re just used to seeing a very narrow silhouette on the bottom.”
Part of the struggle with wearing flares is that if you’re above or below average height, they’re either way too short or pooling around your feet. Whether you’re on the tall or petite side, Kittlitz recommends flares fall about one inch off the ground in order to look their best and properly showcase your shoes.
“We have more benefits in the sense that there are more denim companies that are catering to the variety of types of bodies,” Denee said. “So we have brands, especially denim brands, that are more sensitive to give longer inseams, shorter inseams, because here’s the thing, with a bootcut, you can’t just chop it off if you’re petite.”
(Yeah, that’s definitely one point for skinny jeans.)
Whether you go full force into flares or stick to skinnies, both women agree that no shoe is outright wrong. It’s just about creating the silhouette and style you want.
“This is what I always tell people: It’s all about personal style with shoes. Like, yes, I have that kind of rule of thumb of balancing the silhouette, but shoes are where you can really let your personality shine through. Just roll with it,” Kittlitz said.
“This is the time to kind of have fun and experiment because you’re at home,” Denee said, giving props to anyone who’s jean shopping at all during a pandemic. “Try them on and experiment with shoes you already have to see what kind of leg line you’re giving yourself. It’s going to be different than the skinnies.”
If you’re wondering what these experts wear with their flares, here are their favorite footwear pairings.
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Macy’s

A colorful, pointed-toe flat

“I immediately go to that peek of a toe, peek of color, because you’re going to want to bring some joy to your clothes,” Denee said.
Get them at Macy’s for $69.50.

Dr. Martens

Classic combat boots

“A personal preference would be Docs or platform boots. That’s almost kind of giving you a more Gen Z feel to the outfit,” Kittlitz said.
Get them at Dr. Martens for $150.

Steve Madden

A slimmer, more modern option

Macy’s

Elevated tennis shoes

Shoes.com

Throwback sneakers

“For my personal style, I love a good, chunky dad shoe,” Kittlitz said. “I know they’re not to most people’s tastes, but I really love my Filas as they’re super comfortable. I love that they give a little bit of height, too.”
Get them at Shoes.com for $64.95.