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8 Boots + Shoes I Wear with Flare Jeans & Bell Bottoms in Fall/Winter

8 Boots + Shoes I Wear with Flare Jeans & Bell Bottoms in Fall/Winter

From slight bootcut styles to fully flared-out bell bottoms, flare jeans are still in style for winter 2024

Finding the right shoes to wear with flare jeans and bell bottoms is important, as shoes can make or break your flare jeans outfit!

Before looking at the best shoe styles for flares, let's define what these jeans are–as there seems to be some confusion about them online.

Flare jeans fit slim and straight through the thighs, then flare out down from the knees. The leg opening for flare jeans is over 20″, while bell bottom jeans have a more exaggerated “bell” flare, with a 26″+ opening.

Flare styles today come in ankle, full, or cropped lengths (these shorter ones are called kick flares). With their wider opening, these jeans fit most slim to chunkier shoes & boots.

I'll be grouping flares and bell bottoms in this guide, as similar shoe styles flatter both. If shoes to pair with a more subtle flare are what you're after, check out my article on the best shoes for bootcut jeans.

8 Best Shoes to Wear with Flare Jeans in 2024

To illustrate the best shoes for flare and bell bottom jeans, I'm wearing full length high rise 70s denim flares from GAP in this post. They have a 22″ leg opening, and regular 32″ inseam.

My kick flares high rise are also from GAP, with a 17″ leg opening and a regular 26.25″ inseam. I'm wearing a size 27.

1. Flare Jeans & Ankle Boots

Ankle boots are my go-to shoes for flare jeans or bell bottoms. These are the perfect match from Fall to Spring. The hot ankle boot of the moment has a higher vamp, a square toe and a block heel, like the cream-colored ones I'm wearing above.

These make great boots to wear with flare jeans since they balance out the wider-bottomed proportions and are perfect casual outfits. They have a 3-inch heel, and you can see that I would have had room for a longer flared leg.

I like how the hem rests on the mid-vamp on the boot for a clean look where the bottoms don't buckle over the boots.

Woman wearing flare jeans with pointed toe ankle boots for fall/winter.

You can also opt for a pointed toe or more rounded/almond shape for a softer flare jeans look with your boots.

Whether you choose a classic leather ankle style, sock bootie or platform ankle boot, that is entirely up to you!

I love block heels, but pointed-toe stiletto booties are the perfect pairing for elevated flare jeans outfits, as long as your jeans aren't too long.

If you choose ankle boots with a shaft 5.25 inches or higher (especially with this boot and jean combo) they will look great with all flare lengths.

With cropped, aka kick flares, the current way to style ankle boots is having the jeans cover the boot shaft without exposing any ankle, like the image below. Apparently, ankles are out. I don't make the rules!

Close of up woman wearing blue cropped flared jeans with snake print ankle boots with block heel.

Make sure your ankle boots have a tighter leg opening, so they don't bulge under your jeans. I suggest the jean base to have 2-4 inches of room at the width. This way, the boot tapers inside the jeans, adding shape to the ankle.

Ankle Boots We Love:

Dolce Vita
Sam Edelman

2. Sneakers & Flares for Off-Duty Days

Woman wearing flare jeans with white sneakers outfit for fall/winter.
Gap Flare Jeans // Saucony Sneakers

If you're opting for a sporty & more casual look with your flare jeans, sneakers are the way to go.

I remember wearing my flares with sneakers in high school, right through university & there was nothing more comfortable and cool!

You can play around with different sneaker styles and lengths of flare jeans, even longer ones that bunch at the ankles for a more laid-back look. For a cleaner aesthetic, opt a white sneaker with a slightly lower than ankle hem. This due can be paired easily with any top or sweater.

Retro or classic white sneakers, like Nike Air Force 1s, will work great, but any white sneaker will do!

White Lace-up Sneakers We Love:

White leather lace up sneaker on white background.
TAOs Plim Soul
White leather lace up sneaker on white background.
VEJA Esplar
White with gold heel tab lace up sneaker on white background.
Adidas Stan Smith

My favorite sneaker and flare jeans pairing at the moment is with platforms. Mostly, because I love the lift they give me! Mine are high tops, but you can find low and high versions from many brands.

I prefer to keep the back bottom edge of the jeans aligned with the top of the sneaker's outsole for a more minimal look. A longer flare can work if a Gen Z vibe is what you're after!

A cropped flair can also look great with sneakers, but I would avoid high tops (which can look awkward if jean hem and sneaker top meet. For these jeans, stick to classic sneaker styles and avoid chunky ones.

Platform Sneakers We Love:

White lace up platform sneaker on white background.
White canvas lace up sneaker on white background.
White with light brown patterned heel tab lace up platform sneaker on white background.

3. Long & Kick Flares with Clogs For a Groovy Look

Woman wearing flare jeans with clogs for fall/winter.
Gap Flares & Belt // Free People Knit Tee // Clogs from Winners

Classic clog mules are a fun & retro way to wear with your flare jeans, and especially bell bottom jeans! All brands seem to make them now, from Swedish Hasbeens, to Dr. Schols, Frye and Ugg.

I bought mine from Winners (aka Marshalls in Canada). But you can also reach for sportier clogs, or cozy styles like the popular Birkenstock Bostons.

These shoes will make your feet happy & add a little flair to your…uhm…flares. And any length of flare will look great, especially with classic clogs.

Flat clogs like the Birks will work best with ankle-cropped lengths. And you can style your clogs and flares with chunky or wooly knit socks in fall/winter.

Flare Hemline Tip : If you keep the hemline a little shorter, say 2-3 inches off the ground, the nailing detailing of the clogs will look fun peeking out from underneath!

Clogs We Love:

Swedish Hasbeens
Michael Kors

4. Chunky or Lug Sole Loafers & Flare Jeans

Woman wearing flare jeans with chunky loafers for fall/winter.
Gap Flares // Carmela Loafers // Aritzia Shirt

Thick-soled loafers have been a big trend for the last few seasons, and they make great shoes to wear with flare jeans for casual to business casual occasions.

I like a moderate platform of 1 inch with up to a 2 inch heel, as the loafers will pair well with both cropped & longer length flares, balancing out the proportions of the latter.

For ultra-chunky loafers, with a higher than 3 inch hee/platform, style them mainly with ankle to longer flares and platform, as they will likely overpower kick flares. But let's not forget about classic loafers with a single-sole and lower heel!

Woman wearing kick flare jeans with black loafers and sweater.

You can still style classic, these thin-soled loafers with your flares! These will look best with ankle length & cropped versions and give off a less edgy look.

Socks are trending right now and you can either style white socks with your loafers, choose socks to match your loafer color, or keep things simple with no-show socks. Check out my post on how to style loafers for any occasion for more loafer styling options!

Loafers We Love :

Sam Edelman
Black leather round toe loafers on white background.
ShoeTease Facebook Group block reading: don't know what to wear join our free facebook group for styling and outfit help beside an image of a woman organizing her shoes and another woman standing in a fashionable outfit with jeans.

5. Flare Jeans & Heels to Elevate Your Outfit

I love pointed toe pumps and they're just chef's kiss when paired with full length flare jeans in the Fall!

This pairing is flattering, as it lengthens the leg and gives an updated look to flare jeans. And with mid to dark wash jeans and cute top, you can easily wear the outfit for an evening out, or business casual setting.

Close of up woman's legs wearing blue flared jeans with black stiletto heel pumps.

Higher heels look great here, but be careful with stilettos. If your flare jeans are too long, you risk tripping on the hem, so make sure the jean hem is at least 1 inch from the ground. For reference, my 4 inch heels, above, leave a 3 inch gap from ground to jean hem.

If you're into the popular kitten heels, these look great with cropped and ankle length flare jeans, especially if the heels are slingbacks. Of course, high heel sandals will as well!

Women's Pumps We Love:

Sam Edelman
Steve Madden
Massimo Matteo

Full Length Flare Jeans + Stiletto Heels? No!

Cropped view of lady legs wearing light blue flare jeans with pointy toe shoes that are barely visible, illustrating what shoes not to wear with flare jeans.

With all that bulky fabric near your heels, a little misstep & your stiletto will have you tripping & face-planting in no time. So no, stiletto heels with flare jeans that are too long are a no-no in my books.

And I can't imagine how difficult it must be to walk in a stiletto mule or slide with the weight of your jeans pushing them from side to side, either. Like in the photo above from

Also, if your jeans are so long that your heels stomp over them, you'll puncture or fray the bottom back ends of your pants. I know this from personal experience!

However, if you're desperate to wear your spikey stilettos with flare jeans, opt for shorter length flared jeans to give the base of the heel some breathing room, like I did in the examples above.

6. Chunky Boots with Flares for Winter Outfits

Woman wearing flare jeans with chelsea boots for fall/winter.
Gap Long Flares, Blondo Boots (similar)

In ankle or calf height form, chunky boots work great with flare or bell bottom jeans. Especially the trendy hot Chelsea boots with a high vamp and lug sole, carried over from last season.

But you can't go wrong with combat boot classics like Doc Martens, even more so those with a platform!

Both of these styles and chunky ankle boots in general will work well with any length jeans. However, I advise to pair them with ankle to longer flares and they balance out the wider flare hem.

Close of up woman wearing blue cropped flared jeans with black Chelsea boots.
Blondo Chelsea Boots (similar), GAP Kick Flares

You can also wear chunky boots with kick flares. Just make sure these are tight on the leg and hide inside the jean hem. The chunky Chelsea boots I'm wearing above have a 2.25″ heel, 6″ shaft height and 10″ leg opening. They.

Shop Chunky Ankle Boots:

Calvin Klein
Kenneth Cole
Dolce Vita

7. Ballerina Flats with Kick or Long Flares

Another popular shoe to wear with flare jeans at the moment is the ballerina flat, especially with a squared toe and/or Mary Jane style. But any squared-toe flat will do!

I love these shoes with cropped flares, but many online magazines are styling longer flares with them.

Woman wearing full length flare jeans with Mary Jane flats and black turtleneck.

I'm not a huge fan of that pairing, because full length flare jeans will overwhelm the flats and the hemline will bunch up excessively.

This might be a vibe in an editorial layout, but in real life the styling just isn't practical, as it can look disheveled and messy.

Close of up woman's legs wearing long blue flared jeans with black ballerina flats.

When styling ballerina flats with longer flare jeans, ensure the hem ends right at or above the shoe's base, like above, and doesn't drag on the ground.

Shop Ballerina Flats:


8. Western Boots with Long Flares for a Cowgirl Look

Flare jeans are just made for western boots, especially at ankle to calf height style. The inward curved heel perfectly allows the boot to drape down, while the pointed/almond toe shape curves out from below the hem.

I suggest keeping the full flare hem at least half an inch from the ground for a perfect drape. You can wear your cowboy boots and jeans with a chambray shirt like I have to kick up the western appeal.

Or, trade in your usual ankle boots for a western-inspired business casual outfit like above. I could have added a western belt to match the color of the boots to kick it up a notch, or wear black or black/white boots to play them down.

Kick flares with western boots, on the other hand don't look great. As you can tell from my styling this combo, here.

There's just not enough wiggle room in the pant hem for the larger cowoby-inspired boot shaft, giving an awkward no-ankle appearance. Not my favorite at all, but if you can pull them off, go for it!

Shop Western Ankle Boots:

Marc Fisher LTD
Beige leather pointed toe pull on western boots on white background.
Free People
Alondra Born

Shop Favorite Flare Jeans for Women:

Now That You Know What Shoes to Wear with Flare Jeans

As you've seen, there are many boots and shoes to wear with flare jeans this Fall and Winter. From lower heeled flats to heels and boots, there is something for everyone.

Not ready to make the women's flare jeans leap quite yet? No worries; straight leg and full wide widths are trending! And the styles can be paired with most of the shoes for flare jeans listed in this post 🙂

Thank you Bruna Rico for the amazing photography in this article!

xo ShoeTease 

This post may contain affiliate links. ShoeTease may earn a small commission if you click through and/or make a purchase. Thanks for your support!


Sunday 13th of January 2019

this is the first article I have ever read that said what I've always felt: a more substantial shoe looks best with flare jeans! I'm so glad they're back in style...I was so tired of skinnies and broke up with them...good to know my timing means I'll be in style again for at least a couple years!

6 Shoes to Wear with Flare Jeans in 2015 #ootd #nailart - Urban Angels

Sunday 24th of January 2016

[…] Read More Source: – JanetteSequino // […]


Saturday 26th of December 2015

Thanks for this....I'm pretty clueless about this kind of thing! Would you happen to know where I can buy the jeans pictured?


Sunday 27th of December 2015

Hi LeAnn,

Most of the jeans are linked in the "shop flare jeans" widget (if you're on a computer) & you can also find them by clicking "shop the post" if you're browsing from a mobile device. If you have any questions on a specific style, please don't hesitate to ask, below or email me at shoetease(at)gmail(dot)com. xo Cristina


Saturday 16th of May 2015

I love these tips. They are spot-on. Great job, as usual, Cristina.



Friday 20th of May 2016

I think you are obsessed with foot size. No one ever thinks "omg! Those feet are so long. However, I will agree that wearing a stiletto underneath a flare is tacky.


Wednesday 20th of May 2015

Thanks so much Sharon. Glad you approve! :) xo Cristina