8 Boots + Shoes I’m Wearing with Flare Jeans & Bell Bottoms this 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!

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 come in ankle, full, or cropped lengths (aka kick flares). With their wider opening, these jeans fit most slim to chunkier shoes & boots.

(Related Post: 12+ Best Shoes for Bootcut Jeans)

8 Chic Shoes to Wear with Flare Jeans in 2024/25

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.

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!

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:

2. Sneakers & Flares for Off-Duty Days

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!

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.

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

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!

4. Chunky or Lug Sole Loafers & Flare Jeans

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!

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!

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.

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!

Full Length Flare Jeans + Stiletto Heels? No!

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 weworewhat.com.

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 Chelsea Boots with Flares for Winter Outfits

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.

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.

7. Ballet 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.

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.

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.

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!

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 

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