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11 Boots & Shoes to Wear with Wide Leg Jeans in Fall/Winter

11 Boots & Shoes to Wear with Wide Leg Jeans in Fall/Winter

Women's wide leg jeans continue to trend as a denim staple in 2024. Mostly thanks to Gen Z's fashion influence. These roomy-legged jeans have changed the shoe landscape and how to style them.

Thankfully, when figuring out what shoes to wear with wide-leg jeans, there are many great footwear options for Fall/Winter.

Wide-leg jeans are defined as jeans that fit loosely on the thighs, continuing either straight down or widen down towards the hem.

They can be high to low-waisted, full length or cropped, and with varying degrees of bagginess. What they all have in common is a large opening at the hem, usually over 22″.

Wide leg jeans can flatter most body types with the right fit, length and proper clothing and accessories – like shoes! Choosing the right shoes for wide-leg jeans is an important aspect of styling them!

11 Best Shoes to Style with Wide Leg Jeans 

For reference, I'm wearing Gap Stride Wide-Leg Jeans that flare downwards, both in black and beige. These have a 25″ leg opening I'm fitting a size 27.

1. Ankle Boots

Ankle boots with any wide leg jeans work well. However, with longer versions of the jeans that end right above floor level behind the foot, you'll have more boot options.

You can go for longer full length jeans, but I prefer it when the jean hem ends either 1/4 from the top or base of the heel.

Favorite ankle boots for all wide-leg jeans: square toe and almond toe with a block heel. These look great with all wider denim lengths. You can choose a block or stiletto heels, depending on what look you're going for.

With cropped wide leg jeans, choose an ankle boot with a higher shaft, so there's no break between the top of the boot and edge of the jeans. Just like the heeled boot with wide leg jeans styling below:

Collage of cropped view of 2 women wearing cropped wide leg jeans with high heel ankle boots.

When opting for extra-long jeans, reach for a platform boot with a squared toe and chunky heel so the hem doesn't drown out the boots.

Many high end retailers are styling their wide leg jeans with platform boots, giving an edgy, cool-girl look. But be warned, as it's not the most practical look and can look messy and not all of us can pull it off.

Collage of cropped view of 2 women wearing long wide leg jeans with platform ankle boots.

If the baggy hem is not for you, try cuffing the jeans to create an ankle or cropped length. Cuffing wider denim will work best with straight or tapered-legged jeans.

Wider-legged flared hems won't roll up straight & stay put. I know this because I've tried many times with mine!

As for ankle boot colors, anything goes. Worth noting that off-white, snake print, and silver ankle boots are having a moment. Black, tan, and brown will always be in style, so don't overlook the basics!

Check out more ankle boots with jeans styling tips in my dedicated guide!

Ankle Boots We Love:

Dolce Vita
Sam Edelman

2. Lug Sole Chelsea Boots

Woman wearing wide leg jeans outfit.
Gap Jeans, Tee & Jacket, Blondo Boots (similar)
Woman wearing wide leg jeans outfit.
Gap Jeans, Tee & Belt, Blondo Boots (similar)

Chunky Chelsea boots are a trending style this season, as are similar-soled combat boots. These will look fab under longer wide leg jeans or peeking out of a cropped pair.

Because of their rugged sole, you can wear them will all styles and lengths of wider jeans. Reach for a pair of waterproof ones to style with wide legged jeans all through the winter!

The trendiest combat boots of the season? Black, white, and burgundy in matte leather.

If you prefer to keep your look more classic, a simple black Chelsea or combat boot with a finer sole will still look great paired with ankle length or cropped jeans.

Check out my style guide on how to wear Chelsea boots with jeans of all styles! Keep your tops and jackets on trend with the season by selecting oversized tops and toppers with clean lines.

3. Sneakers

Sneakers are, of course, just as timeless as jeans. So it’s natural that most sneaker styles pair well with wide-leg jeans! But I have a few favorites:

For a sportier and trending look, pair chunky or dad sneakers with wide leg jeans.

I love how my beige and white chunky New Balance 9060s look with my off-white wide-leg jeans. It makes the outfit blend well together and doesn't over-accentuate the shoe.

Chunky Sneakers We Love:

Tan chunky lace up sneaker on white background.
Steve Madden
Blue chunky lace up sneaker on white background.
Fila Disruptor II
Veja Venturi

The same can be said with the black and platform Vans with the white platform. The platform is emphasized, but keeping the rest of the outfit in tone with the shoes, as it balances the look.

As these sneakers are high tops, I could easily roll up the jeans or wear cropped wide legs.

Woman wearing wide leg jeans outfit with white sneakers.

If you want a more polished look with your wide-leg jeans, get an ankle length pair whose color matches or are in tone with the sneakers.

Or choose a pair of classic white lace-up sneakers. These go with everything! Think Nike Air Force 1s, classic Adidas tennis shoes or sleek leather sneaker from Veja or Golden Goose.

For a relaxed, weekend outfit, try a pair of extra long, baggy wide leg jeans with sneakers!

Shop White Leather Sneakers:

White leather lace up sneaker on white background.
TAOs Plim Soul
White leather lace up sneaker on white background.
VEJA Esplar
White with decorative perforation embossing and silver heel tab lace up sneaker on white background.
Vintage Havana
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.

4. Pumps

I don't normally advise wearing pumps – especially stiletto styles – with wide leg jeans. That's because longer styles can drown-out the heels and be a tripping hazard. But not if the wide leg jeans in question are cropped or ankle length!

I'm wearing a shorter full-length jeans with my nude pumps, but I could have also opted for a longer style, given the height of the heels.

Although cropped wide leg jeans with high heel pumps look great, I like the look best when paired with a low kitten heel. Especially one with a curved heel or slingback.

A pointed-toe pump with a high stiletto and long jeans can lengthen the legs, even more so with high-waisted wide-leg jeans. This pairing looks fab on petites or women with longer torsos.

Just make sure the pant hem is at least 1″ above the base of the heel, to avoid stepping on it.

Women's Pumps We Love:

Sam Edelman
Steve Madden
Massimo Matteo

5. Clogs with All Wide Leg Jeans

Woman wearing wide leg jeans outfit with clogs.
Gap Jeans & Belt, Free People Tee, Clogs from Winners

Comfort and the 70s are having their moment, so step right into that groovy era and into a pair of clogs! Black, tan, brown, and other neutral colors all complement wide leg jeans.

To keep the look more subtle, match them to the denim color like I did, pairing black and brown-soled clogs with black wide leg jeans. For more contrast, try a caramel-colored or metallic clog with blue, or black jeans.

Opt for slip-on clog mules with cropped wide leg jeans. I suggest sling-back or ankle strap clogs with longer jeans styles so the shoes don't slip off as you walk.

Don't let the jean hem hide the studded detailing around the shoe's base–those are the stars of this shoe-show!

Add wooly socks or speckled knit socks with clogs for added styling in the fall/winter months. Or grab a pair of furry-lined clogs! Complete the look with a long-sleeved tee and a cozy cardigan.

Check out my post on how to wear clogs for head-to-toe styling tips!

Clogs We Love:

Swedish Hasbeens
Michael Kors

6. Strappy Sandals

Woman wearing wide leg jeans outfit high heel sandals.

Strappy sandals with wide-leg jeans can lighten the look of these heftier jeans and elevate your look, creating a more refined outfit.

Cropped wide-leg jeans will show off ankle straps, or any details along the ankles of back of the heel. Sheer or metallic mesh socks can be fun too! With longer jeans, try a platform sandal with a block heel.

Shop Strappy Stilettos:

Black leather square toe adjustable ankle buckle closure sandal heels on white background.
Stuart Weitzman
Beige patent leather strappy stiletto sandals on white background.
Calvin Klein
Stuart Weitzman

7. Classic & Chunky Loafers

Collage of 4 women wearing different wide leg jeans with loafers.

Thicker-soled loafers with wider jeans are extremely on trend for 2024! For boxier, wider-leg jean styles, choose chunky soled loafers, with or without metallic hardware or a patent finish.

To create a more classic look, try full length or cropped wide leg jeans with a single-soled loafers. Like horsebit or simple penny loafers. These are more conservative shoes with wider leg jeans, which can create preppy or business casual outfits. Just add a simple blouse under a button-front cardigan.

Cropped wide-leg jeans style well with all loafer styles, including loafer mules. That said, this style isn't as popular now as they were a few seasons ago.

Loafers We Love :

Sam Edelman
Black leather round toe loafers on white background.

8. Western Boots

Western boots are low-key boots that look great with everything, including wide leg jeans!

Whether your wide leg jeans are floor length, or over the ankle, all western style boots will pair well. You can choose a lower-shaft cowboy bootie, or a calf height style with a wider legged jean.

Complete your outfit with a crisp blouse, cosy sweater or double your denim with a chambray shirt and/or jean jacket! I love a cozy sweater and a western belt in the fall to give the outfit some flair!

Shop Western Ankle Boots:

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

9. Ballerina Flats

Cropped view of woman wearing full length wide leg jeans with ballerina flats.
Cropped view of woman wearing cuffed wide leg jeans with ballerina flats.

Ballerina flats with discreet square toe shapes are the spotlit shoe of the season. And yes, they can look great with wide leg jeans if the styling is on point.

I love a classic ballet flat with a Mary Jane strap paired with cropped or ankle length wide jeans. This combo gives a playful look that shows off a little ankle. You can even add cute socks for some flair.

That said, even full length wide jeans can work, as long as the hem doesn't pass the base of the heel and do more than graze the floor. Anything longer could look messy and cause you to walk over your jean hem.

Collage of 4 women wearing different wide leg jeans with ballerina flats.

Shop Ballerina Flats:


10. Calf Height Boots

Woman wearing wide leg jeans outfit with leopard print calf boots.
Woman wearing cuffed wide leg jeans outfit with leopard print calf boots.

Taller boots with wide leg jeans don't usually make sense, but sometimes they do! Cropped wide leg jeans that fall over a calf or knee boot will look fab. This shows off more of the boot.

But if your wide leg jeans are longer and you have a lovely shaped taller boot, what's stopping you?

A tight, sock-like calf boot with a cropped wide leg jean will look more elevated, especially with a finer heel. In contrast, a combat/Chelsea style will look more rugged, while a platform calf boot will look edgier.

11. Platform Shoes and Boots

Collage of 4 women wearing different Platform shoes with wide leg jeans.

You'd be hard-pressed to find a platform shoe that doesn't go well with wide leg jeans. As a stylist, I appreciate the visual balance when pairing a more substantial jean–like wide or flared ones–with a bulkier shoe.

I prefer to style platform shoes with ankle length or full length wider jeans for better below-the-knee proportions.

In high winter, try a platform lug heeled boot with chunky heels with your wide leg jeans for a casual look with a tucked-in cardigan.

For a night out, try a velvet or suede platform sandal for a fun night out, and add interest with a semi-opaque polka dot stocking.

There is a ton of platform footwear, including fisherman sandals, clogs, loafers and pumps that look great with wide leg jeans too, so shop around to see what you like best!

Now That You Know Shoes to Wear with Wide Leg Jeans

I hope I've given you some great ideas on what shoes to wear with wide leg jeans this Fall/Winter!

As you've seen, there is no shortage of classic and trendy styles to style with your wider jeans, including cropped and full length options.

Which shoes would you choose?

For me, it's a more substantial shoe like as a sturdy sandal with a block heel, or platform ankle boot. I love creating edgy looks with wide jeans and thicker shoes.

If I’ve missed one of your preferred types of shoes for wide leg jeans, let me know in the comments, below!

xo Cristina

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