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11 Stylish Shoes to Wear with Wide Leg Pants This Fall/Winter

11 Stylish Shoes to Wear with Wide Leg Pants This Fall/Winter

Comfort is key to trending women's dress pants in 2024, and it's no surprise that wide-leg pants are currently the most coveted pant style!

Thankfully, there are many great shoes to wear with wide-leg pants to complete your outfit in style.

In this in-depth styling guide, my 20 years of experience in the fashion industry will guide you on how to style wide-leg pants with the right shoes!

These include 11 of my top choice footwear from flats, sneakers and boots for wide leg dress pants to wear in Fall/Winter.

(Related: Shoes for Cropped Dress Pants / Shoes to Wear with Wide-Leg Jeans)

14 Best Shoes to Wear with Wide-leg Pants

For reference, I'm wearing these wide leg pants from Banana Republic. They are very high-waisted with a 30″ inseam and 22″ leg opening in an oversized fit.

1. Chunky Chelsea Boots

Woman wearing chunky Chelsea boots with wide leg pants.
Banana Republic Pants // GAP Jacket // Blondo Boots (similar)

Spring and fall are the perfect seasons to wear Chelsea boots outfits with wide-leg trousers. Lug sole Chelsea boots are all the rage and will give your wide-leg pants outfit a solid edge.

Try to keep the pants' hem landing somewhere between the middle of the boot's heel, for an easy combo you can even wear to work.

Go for higher-shaft Chelsea boots with cropped wide-leg pants to show off more of your boot and give a sportier vibe.

For an edgier outfit, try a pair of baggy, wider-legged pants that fall over the boots, making sure they don't drag on the floor.

Of course, if a lug sole combat boot style is more your preference, these will look great with wider leg pants too. And the same styling tips as above apply!

Chelsea Boots We Love:

Dr.Martens
SHOP
Sorel
SHOP
Blundstone
SHOP

2. Pointed Pumps

Banana Republic Pants // Louboutin Pumps (similar)

Heeled pumps do not disappoint with wide-legged pants! Especially for more refined outfits.

Pointed-toe pumps with finer heels in particular will lighten the look of your wide dress pants. These are a great combo for more elegant looks for dressing up wider pants for a night out or a classy business look.

Pumps work best with ankle or cropped wide-leg pants, even more so if the front or heel portions are adorned with bows or jewel details. 

I've seen many publications and street-style fashions styling long, wide trousers that waterfall over pointed pumps or booties. For everyday dressing, this isn't a practical look, as you'll end up walking on the pant hem with every step!

To avoid this, make sure your pant hem ends at least 1/2″ above the heel. I like to wear my full length wide leg pants that end around the middle of the heel of above 1/3 half of the heel.

Especially with stilettos so that I can show them off. Kitten heel pumps look good with both ankle or cropped dress pants.

Women's Pumps We Love:

Sam Edelman
SHOP
Steve Madden
SHOP
Massimo Matteo
SHOP

3. Classic White Sneakers

Classic white sneakers are casual shoes that go with everything, so it's no surprise to find them in a wide-leg pant styling post!

For maximum versatility, choose everyday white sneakers like Nike Air Force 1s, Veja, Adidas classic sneakers, or a simple white tennis sneaker like I'm wearing in the photo above.

These can be styled both casually or even business casual with black wide leg pants and the right top and accessories.

I love a white sneaker and trouser combo with a tucked-in light knit turtleneck, and a peacoat for a trendy, cold-weather look.

White Lace-up Sneakers We Love:

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

Chunky sneakers also look great with wide-leg pants, giving a more rugged alternative to the classic white tennis shoes These include dad sneakers, platform sneakers, retro sneakers, and sneakers with a chunky sole.

This pairing comes back to my love of heftier footwear with wide pants for more casual looks! With a chunky sporty shoe, you can wear your wide pants, long overtop. The chunky outsoles will prevent the pants from dragging on the ground.

The great thing about chunky sneakers is that they can be worn all year round. They even sell some sneaker boots you can there. Pair them with wide-leg pants and an oversized knit sweater for a cozy, but chic look.

Chunky Sneakers We Love:

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

5. Square-Toe Ankle Boots

Ankle boots are perfect for Fall with wide leg pants. They are the IT combo at the moment.

For a trendy look, square-toe boots with a block heel is where it's at. Ankle boots with a higher shaft will suit all lengths of wider pants, including cropped styles. The boot shape balances out a wider pant leg with an oversize sweater, like I'm wearing above.

The key with shorter dress pants is to make sure the boot fully hides under the pant, for the most up-to-date look.

Shop Square-toe Boots:

Marc Fisher LTD
SHOP
Reformation
SHOP
Gray leather square toe heeled boots on white background.
Andre Assous
SHOP

6. Pointed Toe Booties

If a square-toe boot isn't your style, don't worry! Pointed toe or almond-shaped ankle boots will look great, while suiting more elevated looks.

A black leather or patent ankle bootie with a pointed toe and a stiletto heel will be the fanciest shoe to pair with wide black pants and a fancy top, such as a silk camisole.

7. Loafers Make Great Office or Everyday Looks

Banana Republic Pants // Carmela Loafers // Aritzia Shirt

Loafers continue to trend in classic penny loafers and chunkier styles. The loafer style you choose will determine which wide leg pant works best.

Chunky loafers are an excellent option for those who want a little bit of extra height and edge to their outfit. Wear them with longer wide leg pants or ankle length ones, adding white socks for style and warmth.

They are great even for work attire when paired with flowy wide pants and a cargo style shirt or a tailored blazer.

With less chunky, single-soled loafers, extra wide or long dress pants aren't as easy to style. Reach for a cropped or ankle version instead in a less wide leg, for a more classic, streamlined look.

Loafers We Love :

Sam Edelman
SHOP
Agathea
SHOP
Black leather round toe loafers on white background.
Prada
SHOP

8. Clogs

Banana Republic Pants // Clogs from Winners

Clogs are a unique shoe style that has come a long way, continuing to trend into the mid-2020s.

Usually made of wood and rustic-looking, you can find a variety of styles for spring/summer and even fuzzy-lined ones for winter. They're a great alternative to loafers or classic ankle boots, if you want to switch things up a bit!

Clogs look fab with many outfits, including wide-leg pants. High-end designers are styling low-heeled clog flats with baggy, wide-leg pants. I prefer to style mine with a more classic clog because they have those little gold studs to add interest.

If your clogs are more traditional looking and include studs, feel free to show them off with ankle-length or even cropped wide pants.

Learn more about how to How to Wear Clogs in my dedicated post!

Clogs We Love:

Swedish Hasbeens
SHOP
Kork-Ease
SHOP
Michael Kors
SHOP

9. Strappy Heeled Sandals

Banana Republic Pants // Chambray Shirt (similar)

Strappy sandals are best worn with ankle or cropped wide-leg pants to show off straps, especially if they crisscross above the ankles. You can wear your strappy sandals with wide-ankle pants during transitional seasons.

With full-length, wide-legged pants sandals, you'll want your pant leg to end at least a half inch above the first toe strap, and fall at the middle of the heel at the back.

A cropped dress pants works best for a low to kitten heeled sandal, to balance out the proportions of a wider hem.

Shop Strappy Stilettos:

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

10. Ballerina Flats (with the Right Length Pant!)

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

The newest shoe of the season is the ballerina flat. It's a surprising shoe compared to all the chunkier styles of boots and loafers around, and a trickier shoe to style with wide leg pants.

That said, it's possible to wear these trendy flats and look great in wide leg pants. You just have to be careful with hemlines and toe shapes.

A suggest a modern ballerina flat with a squared-toe shape, so it won't get drowned out by a wider pant hem. Ankle length trousers will be the easiest to style, but a full length pant will work as long as the pant hem end at least 1/2” off the floor.

Collage of cropped pant view of 4 women wearing different ballerina with wide leg jeans of different lengths.

You can also choose a pointed-toe flat. These look better with ankle or cropped wide dress pants.

This pairing makes a great look for the office with a blazer and tee, or for more upscale venue in a black camisole and cosy cardigan.

11. Platform Shoes

3 women wearing platform shoes with wide leg pants and trousers.

Platforms are great shoes to wear with wide-leg pants for ladies. I love a more substantial shoe, especially with wide-leg pants, to balance all that fabric – even more so for longer, baggy versions. 

That being said, whether your wide-legged pants are long, cropped, or ankle-length, any platform shoe, boot or sandal will work!

Satin or velvet platform sandals or pumps with wide-leg pants are fabulous for fancier occasions. These work well with ankle length wide leg pants. For an edgy look, try leather platform boots.

When wearing longer length wide trousers with closed-toe shoes, it's most practical and aesthetic for the hemline to end 1-2′ above the toe box area, as shown above.

Are wide-leg pants in style in 2024? 

Yes, they most surely are! Women's wide-leg pants have arguably become one of the top trending over the past few seasons and I routinely include them in my capsule wardrobe collections.

Women's wide-leg pants can be cropped, ankle-length, or super baggy. If you choose cropped or ankle height wide-leg pants, many more shoe opportunities open up, and a chance to show off that footwear!

The most popular pants for women are high-waisted wide-leg pants, but they can also be found in a medium rise. With the right shoes and accessories, they can easily be dressed up or down.

Shop For Wide Leg Pants and Trousers below:

Final Thoughts on Shoes to Wear with Wide Leg Pants

If you're on the lookout for the best shoes to wear with wide-leg pants, there is no shortage of fun, classic and trendy styles to style with your wider dress pants!

Whether you're looking to wear these chic pants to a party, for a casual outing, to the office, or on a date, you will surely find a shoe, boot, sneaker, and heel that will look great.

Wide-leg pant outfits are a comfortable, trendy look that you should definitely try. No offense to skinnier pants!

What kind of outfits and shoes with wide-leg pants do you prefer to wear? Let me know in the comments right down below. If I've missed any, I'll do my best to add it to the above list.

Text reading best shoes to wear with wide leg pants under woman wearing pink outfit with wide leg pants.
9 women wearing different shoes with wide leg pants under text reading 14 best shoes to wear with wide leg pants.

xo ShoeTease

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Catrena

Saturday 15th of October 2022

Fabulous article and great guide!