You may be wondering what shoes to wear with cropped pants in winter and how to style them.
The right pair of shoes can make or break an outfit and when it comes to cropped pants, the right shoes are essential for a put-together look.
Cropped pants are a great way to show off your favorite shoes in the winter months as they won’t let your shoes be hidden by your pant leg!
What if you don’t have any cute shoes to wear with them? The obvious fix is to find a pair of shoes that will help bring your outfit together!
35+ Winter Shoes to Wear With Cropped Pants
Here’s the scoop on what shoes to wear with cropped pants in winter!
1. Sam Edelman Women’s Combat Boots
First up on our list of what shoes to wear with cropped pants in winter is the Sam Edelman Women’s Combat Boots!
This military-inspired boot is made of 100% leather and features a waterproof design to keep your feet dry in any weather.
The platform sole provides support and comfort while showing off your personal style, whether you’re hiking on nature trails or strolling through town.
Choose from distressed or soft tumbled leather in a variety of colors to fit your style.
While this is not necessarily a flat shoe, the heel and sole offer the same amount of lift so you can easily move in them.
2. Sam Edelman Women’s Lydell Combat Boot
Our next choice for what shoes to wear with cropped pants in winter is the Sam Eldeman Lydell Combat Boots.
This boot is the perfect way for the woman to achieve both comfort and style.
The Lydell is constructed with a soft, sock panel and a sturdy leather structure.
It is also water resistant, making it perfect for any terrain or weather conditions.
The lace-up closure provides a secure fit, while the elongated toe style gives you a polished look.
So whether you’re heading to the office in dress pants or out for a night on the town in a pair of slim jeans, the Lydell Combat Boot will surely be a great look!
3. Sam Edelman Women’s Winnie Boot
This is the Sam Edelman Women’s Winnie Boot, a chic and comfortable boot that is perfect for any occasion.
Made in the USA or imported, this boot features a rubber sole and kitten heel that measure approximately 3 inches.
The embroidered suede detail and wrap design make this boot stand out from the rest.
The Sam Edelman name ensures quality craftsmanship.
Whether you’re dressing up for a night out or just looking for a stylish and comfortable boot to wear around town, the Winnie Boot is the perfect choice.
4. Sam Edelman Winona
Looking for a stylish and comfortable boot to keep your feet warm in the colder months? Look no further than the Sam Edelman Winona!
This boot is crafted from velutto suede leather, ensuring both style and comfort.
The grey iris color on the top of your boot is perfect for matching any outfit, and the 5.5″ shaft provides plenty of coverage to keep your feet warm.
The 9.75″ boot opening makes it easy to slip on and off, and the cushioned insole provides hours of comfortable wear.
Whether you’re running errands or headed out for a night on the town, it is sure to become your go-to boot this season!
5. Sam Edelman Thelma Chelsea Boot
The Sam Edelman Thelma Chelsea Boot, the perfect ankle boot for stylish city strolling.
These versatile boots are crafted from premium leather and feature man-made lining and insoles for exceptional comfort.
The pull-on design features elasticized gore panels for a snug, custom fit.
The square pointy toe silhouette provides a chic finishing touch.
Dress them up with a pair of opaque tights or down with wide-leg jeans, the Thelma Boots are sure to become your new go-to footwear choice.
6. Soda Glove Ankle Boot
Another great option for what shoes to wear with cropped pants in winter is the Soda Glove Ankle Boot!
This boot is perfect for stylish, sporty, and sexy looks.
A good thing is that the shoes are made from 100% suede, so they’re comfortable and fashionable.
The lug sole platform heels provide the perfect pairing of style and function.
Plus, the elastic gore makes it easy to slip on and off. Whether you’re hitting the streets or the trails, this boot is sure to turn heads.
So don’t wait any longer, order your pair today!
7. LUCKY STEP Chunky Platform Sneakers
Presenting the LUCKY STEP Chunky Platform Sneakers!
These chunky sneakers will go well with so many outfits, like a crop top with black pants.
The upper and sole are made using lightweight material, making the shoes super comfortable.
You can easily wear socks with these shoes and still look great.
These sneakers will surely accentuate your outfit details!
White sneakers are such a classic shoe choice, so don’t hold off, get your pair today!
8. PiePieBuy Women’s Tie Knot Chelsea Pump Ankle Boots
Trying to find a better option for cute winter fashion? The PiePieBuy Women’s Tie Knot Chelsea Pump Ankle Boots are a good choice!
This style of shoe is made of high-quality synthetic materials and features a chunky stacked heel, side strappy bowtie, and zipper.
They are perfect for dressing up or down and will add a touch of fashion to any outfit such as with capri pants.
They are also extremely comfortable with a cushioned insole that snuggles your feet with every step.
Whether you’re headed to the office, out on the town, or just running errands, these boots are a great choice.
9. DREAM PAIRS Women’s Chunky High Heel Ankle Booties
A stylish and comfortable pair of booties to complete your fall wardrobe? Look no further than the DREAM PAIRS Women’s Chunky High Heel Ankle Booties!
Made with a manmade sole and heel measuring approximately 3.5 inches.
These high heels are one of the best ways to look not only stylish but also very comfortable.
The classic look in these posh booties will make you stand out in any crowd.
The faux fur lining and durable rubber outsole ensure that your feet will stay warm and cozy all day long.
Put them together with some long pants or ankle length skinny pants.
So don’t wait any longer, order your very own pair!
10. Kathemoi Womens Ankle Boots
Next up for what shoes to wear with cropped pants in winter is the Kathemoi Womens Ankle Boots!
Made from environmental faux leather, these boots are designed with a side V cutout and pointed toe for a fashionable look.
The chunky stacked heel and slip-on design make them perfect for all-day wear, whether you’re running errands or dressing up for a night out.
Plus, they come in versatile neutrals that will go with a number of outfit combinations.
Pair them with some ankle pants and a black leather jacket for a unique look!
Order your pair today and enjoy the best of fashion and function!
11. Women’s Western Booties
Comfortable boot to take your outfits to the next level? Then check out our women’s Western Booties!
These booties are made from a soft faux leather and have a rubber sole for comfort and durability.
They also feature a cut-out-side design detail that allows them to easily slip on your foot.
The cowgirl inspired styling can be paired with jeans or dresses for a western flair to any outfit.
So don’t wait any longer, order your pair of Western Booties today!
12. SOREL Women’s Out ‘N About Wedge Boots
The best walking companion you’ll ever have, the SOREL Women’s Out ‘N About Wedge Boots.
These fabulous boots are imported, with a suede sole and heel measuring approximately 2 inches.
They come in a variety of colors to match any outfit such as wide leg pants.
Plus their sporty wedge bootie design makes them both stylish and functional.
They’re waterproof, so you can embrace rainy days without worry.
Their molded rubber soles and high traction protect your feet during long walks in sudden showers or bad weather.
Additionally, their removable, molded, PU-like EVA footbeds and textile lining provide support and comfort for all.
13. Mysoft Women’s Zipper Bootie
The Mysoft Women’s Zipper Bootie is the newest booties that are taking the fashion world by storm!
These booties feature a smooth and streamlined design that is minimalistic and contemporary.
The heel height is approximately 3 inches and the platform height is 0.6 inches.
Plus, the faux leather upper with an extra depth design and round toe shoes eliminates pressure on toes, making these booties perfect for walking miles and miles while traveling.
The side zipper grants the ability to slide your new favorite booties on and off with ease.
The cushioned insole provides maximum comfort with every step while the sturdy outsole ensures prolonged wear.
Take on the colder weather with a stylish pants outfit in these booties
14. SOREL Women’s Out ‘N About Slip-On Wedge Boots
Search no further for what shoes to wear with cropped pants in winter than the SOREL Women’s Out ‘N About Slip-On Wedge Boot!
These wedges are made with high-quality suede or full-grain leather and traditional construction techniques for a boot that is both fashionable and comfortable.
The wide open collar and elastic panels make them easy to slip on.
Plus, they can be worn with a skirt or dress for a dressed-up look, or with skinny jeans or a skirt for a more casual look.
Whether you’re running errands or heading out for a night on the town, they are sure to keep you looking stylish.
15. Lucky Brand Basel
If you’re looking for a comfortable and stylish ankle bootie, the Lucky Brand Basel is a great option.
This sock bootie features one of the easiest ways to get on and off and a stacked block heel for a touch of glamor.
The upper is made of suede leather for a luxurious look and feel, and the synthetic lining ensures your feet will stay comfortable all day long in a pair of tights.
Whether you’re wearing jeans or a skirt, the Basel is the perfect choice for any outfit.
16. Vince Camuto Women’s Allost Pointy Toe Bootie Ankle Boot
Next up is the Vince Camuto Women’s Allost Pointy Toe Bootie Ankle Boot.
This boot is sure to turn heads with its sleek and stylish design. It’s made with high-quality materials, including a leather upper and synthetic sole.
The shaft measures approximately ankle from arch and the heel measures approximately 3.15 inches. The boot opening measures approximately 5.5″ around.
The boot also features a nylon zipper closure for easy on and off that you can wear with a special genre of a thin sock.
17. DREAM PAIRS Women’s FRE High Heels Chelsea Style Ankle Bootie
Dream a dream of DREAM PAIRS Women’s FRE High Heels Chelsea Style Ankle Bootie!
The posh high-heel sandal features a classic clean sleek look, with synthetic soles and stylish high chunky heels.
Shaped with soft suede upper, and double gore panels for a secure and flexible fit, these booties are perfect for any occasion.
Product measurements were taken using size 7 US, width M.
Get your hands on a pair of these fabulous booties today!
18. IDIFU Women’s Ada Fashion Square Toe Ankle Boots
These are the IDIFU Women’s Ada Fashion Square Toe Ankle Boots!
These stylish and comfortable ankle boots are perfect for any occasion.
Whether you’re dressing up for a special event or just heading to work.
The closed square toe and chunky heel provide long-lasting comfort and stability, while the breathable lining and slip-resistant sole keep you feeling good all day long.
With endless outfit possibilities, these versatile boots will become your go-to choice for any outfit.
19. See By Chloe SB23063 Women Bootie
See by Chloe SB23063 Women Bootie’s are a tan boot with a block wedge heel.
This shoe could only be worn by someone who wants to own the room.
The eye-catching women’s bootie is made for everyday wear and comfort and will add a pop of color to your outfit.
20. MARCOREPUBLIC Moscow Slip On
What about a pair of flat sandals that are fashionable and perfect for any event? Welcome the MARCOREPUBLIC Moscow Slip on!
MARCOREPUBLIC strappy sandals have a heel measure of approximately 2.5 inches with a shaft height of 7 inches.
They are textured around the booties that are non-skid traction and have a smooth premium vegan material.
Additionally, top stitching, a soft interior lining, and a side cut-out design give the booties a stylish look.
These casual, sexy, stylish, and trendy make these flat slingbacks a perfect choice for everyday wear!
21. Circus by Sam Edelman Women’s Freddie Ankle Boot
A Cirus by Sam Edelman Women’s Freddie Ankle Boot is an all day comfort 4 inch bootie, perfect for any occasion.
This shoe is designed perfectly for your skin tone and pairs great with wide-leg pants or a cute pair of mules, giving you a refined look.
So why wait, and miss out on this bootie? Get yours before it’s too late!
22. Sam Edelman Women’s Nina Boots
No wonder you can’t find the perfect boot for this occasion! That’s because you don’t have Sam Eldeman Women’s Nina Boots in your closet.
These boots feature a man made sole with a 1.25 heel and a lace up closure.
This boot is made with Cowhide leather with a burnished heel and toe.
Don’t leave your house again without the Sam Edelman boots!
23. Sam Edelman Women’s Jalyn Chelsea Boot
Get ready for a business in the front and a party in the back with Jalyn, the studded bootie that has it all.
Not only does this boot have style but its height at approximately 1.5 inches.
Also, this boot has a round toe style but a synthetic sole to provide you the best comfort.
This boot is not just made for walking but made for any occasion.
Snag you a pair today of Sam Edelman Women’s Jalyn Chelsa Boot, you will not regret it!
24. Sam Edelman Women’s Codie Fashion Boot
The Sam Edelman Women’s Codie Fashion Boot were made just for you!
These shoes feature the perfect square toe and flared heel in the perfect bubble gum pink.
Additionally, the boot’s opening measure approximately 11.81 inches around with a synthetic sole.
The Codie is the perfect everyday bootie made with you in mind.
25. Circus by Sam Edelman Women’s Wesley Western Boot
Where fashion meets western, the Wesley boot is your new go to staple!
The Welsey Western Boot is black with a padded insole and has a 100% synthetic sole.
The Cirus by Sam Edelman Women’s Welsey Western Boot would be a perfect addition to your closet.
26. Sam Edelman Loraine Loafers
The Loraine Loafer is totally sophisticated and just a little bit quirky.
The sleek sole and gold hardware dress up this shoe with a little lifted sole.
Pair it with a pair of trousers, and a cashmere turtleneck!
These loafers would also be great in warmer weather, making them a year-round fashion-girl favorite.
The polished Sam Edelman Women’s Loraine Loafers are what your work wardrobe has been longing for.
27. SOUL Naturalizer Women’s Haley-lace Ankle Boot
The SOUL Naturalizer Women’s Haley-Lace Ankle Boot is great to wear anywhere at any time of year.
This boot has an upper almond toe and a lace up ankle wedge heel.
This ankle boot has a lightweight flexible outsole, and the shoe will help support your ankle bone.
28. Sam Edelman Carlysle Fashion Boot
This perfect everyday bootie has a comfortable block heel suitable for day to night wear.
The Sam Edelman Carlysle Fashion Boot features a leather sole with an inner ankle zipper closure.
These square toe boots are perfect for any outfit of choice and our next pick for what shoes to wear with cropped pants in winter!
29. Naturalizer Women’s Myla Ankle Boot
Have your boots from last year become worn out? Check out the Naturalizer Women’s Myla Ankle Boot that has a comfortable waterproof with a non-slip waterproof sole.
This boot is contoured with a premium fit for all day comfort.
The Myla Ankle Boots are made with waterproof leather suede and have a 2.75 inch heel.
These boots are great for both sunny days and rainy days.
30. Lucky Brand Womens Ballet Flats
Ballet flats are super stylish all year round, and these Lucky Brand Womens Ballet Flats are no exception!
These ballerina flats are made of 100% leather and come in a wide range of colors and designs.
They are perfect to pair with any outfit, whether it be casual wear or a more professional look.
A pair of neutral flats really completes an outfit, so don’t miss out on these ballet pumps!
31. Sam Edelman Women’s Anika Fashion Boot
Anika’s elegantly pointed toe and sleek contrasting heel will have you feeling like a supermodel.
This fashion boot heel height is 3.25 inches with a square toe style.
These chic boots are great for dinner with black culottes or even for brunch with straight leg jeans.
You can’t miss out on these boots.
Not only will you feel like Kendall Jenner but these boots will make you stand out from the rest.
32. Sam Edelman Women’s Lydell Boots
This boot meets combat in this perfect lug sole look. Pair with an array of outfits for a chic street style look.
The Sam Edelman Women’s Lydell Boots have Cowhide suede leather with a rubber sole.
The signature logo is the hardware on the heel with soft knit panels to complete this gorgeous shoe.
Show off your shoes better than knee-high boots with pants with the Sam Edelman Women’s Lydell Boots!
33. Kolton Chelsea Boot
The sleek Oxford bootie with a dependable and firm sole easily slips on and of for maximum comfort.
There’s an 11.02 inch boot opening with a synthetic sole in these Oxford shoes.
The Sam Edelman Women’s Kolton Chelsea Boot is great for everyday wear and perfect for any outfit.
Grab your Kolton Chelsea Boot today!
34. Naturalizer Women’s Madalynngore Ankle Boot
Next up we have another great option from their Weather Ready collection, the Naturalizer Women’s Madalynngore Ankle Boot.
When wet weather hits, you’ll be more than prepared with the comfortable, water-repellent Chelsea boot with a capable lug sole.
A side zipper, flexible goring, and back pull tab allow for easy entrance.
If you’re having a rainy day these booties are the ones to pull from your closet.
35. Naturalizer Women’s Varuna Booties Ankle Boot
A boot that has a flexible sole and seam sealed waterproof leather? Introducing the Naturalizer Women’s Varuna Booties Ankle Boot!
This boot has a suede almond shape toe.
The rubber sole on these boots gives comfort for long time wear and the heel height is approximately 2.95 inches.
This boot is perfect for any occasion!
So grab your Varuna Booties today!
36. Naturalizer Women’s Callie Ankle Boot
This limited edition ankle boot is a lace up block heel that is versatile with a lug sole.
The Callie Ankle Boot is made with 100% fabric and made in the USA.
The leather upper almond toe boot could be worn with any outfit you chose.
That is the scoop on what shoes to wear with crop pants in winter!
Any of the boots on this list will have you feeling like Audrey Hepburn! There is no such thing as the wrong pair of shoes with this list.
So get creative with how you style these shoes. There are plenty of other ways to wear them other than a pair of black crop jeans.
You can wear them with a skirt and thick tights, white socks or an oversized shirt!
For a more elegant look, you can pair Chelsea Boots with a special genre of thin sock!
No matter what you choose you will look amazing this winter.
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