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25 Best Styles: What Shoes to Wear with Cropped Jeans

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Cropped jeans are my absolute favorite style of jeans to wear! Ankle length jeans are so versatile. You can wear them with just about any shoes. And in every season of the year, casually, professionally, or for date night. 

As someone who always loved Audrey Hepburn’s iconic short, slim-fitting pants look of the 1950s, I love channeling that look in jeans and pants! 

What are crop jeans?

Crop jeans are universally flattering denim pants that stop at or above the ankle. They are longer than capri pants. Capris stop higher up on the calf. For the most flattering look, choose slim fitting jeans that stop at the narrowest spot on your ankle. Skinny jeans, crop flare, straight jeans, wide leg crops and boyfriend jeans are all different styles of crop jeans. 

Styles of cropped jeans
Photo Credits, Top Left to Right: Loft, Gap, Levi’s, Front Left to Right: Everlane, J.Crew Factory

Skinny jeans are tapered and slim fitting from the knee down. 

Crop flares or kick crop flares stop at or above the ankle and have a slight flare at the hem. The flare is less pronounced than you see on long flare jeans. They are a great option for wider hips since the flare balances out the width of the hips. 

As the name implies, straight jeans are straight from the knee down. If you fold the hem of your straight jeans up to the knee, the width will be the same at both spots. It’s helpful to know that there are also styles of straight jeans that are tapered, so they’re slimmer fitting but roomier at the ankle than skinny jeans. 

Wide leg crop jeans are fitted in the waist and hips with a wide leg from the hip down, stopping at or above the ankle. This is another style that can work well for wider hips since they’re roomier overall.

Boyfriend jeans are a looser fitting jean all over that are cuffed, stopping at or above the ankle for an overall relaxed and easy look. 

You may be amazed by all the different shoe styles that work with cropped jeans, from flat sandals to ankle boots. 

I’m here to be your style guide and pulled 25 shoe styles to show you, along with style tips for choosing the best shoes to wear with crop jeans for casual outings, work, and nights out on the town. Let’s dive in! 

What shoes can you wear with cropped jeans?

Casual shoes with cropped jeans

Crop flare jeans with leather flip flops

Leather flip-flops are a good option on hot days that you just need to run out the door and go. They’re more elevated than your usual rubber flip-flops. Here I’m pairing them with a white tank cropped top and black crop flare jeans.

Crop flare jeans with leather flip flops

Jeans | Similar Shoes

These jeans have a high waist and work well with a longer crop top. The flare makes them slightly wider at the ankle. That width helps to balance out the width of my hips so I look more proportional overall. For reference, I’m a size small up top and wear size 12 jeans on the bottom. 

Straight jeans with flat sandals with ankle straps

Here I’m wearing black ankle strap sandals that coordinate with my black top and bag. This is such a good look! Sandals with ankle straps are some of my favorite shoes to wear with crop jeans.

Straight jeans with flat sandals with ankle straps

Jeans | Sandals

These are straight jeans and the hem is the same width as the knee. If you’ve been stumped about how to wear ankle strap sandals with straight jeans, it’s possible your straight jeans are tapered and too tight at the ankle. When you go to buy a new pair of straight jeans, first thing, fold the hem up to the knee to see if the width of the hem is narrower than the width of the knee. Notice how with this pair, the hem of the jeans is wide enough to fit the ankle strap up underneath. Also, the jeans are just short enough so the hem doesn’t get caught up on the ankle strap. 

Here’s a style tip for you. A great way to be sure that your ankle strap sandals don’t chop up your legs and shorten your leg line is to look for a pair with the thinnest strap possible and that matches your skin tone. This is a rule I’m deliberately breaking in this look, because I love these sandals so much. Rules are means to be broken. Wink, wink.

Wide leg cropped pants with ankle wrap sandals

Ankle wrap sandals also work great with wide leg cropped pants. I’m still working on finding wide leg cropped jeans that I love, but I want you to see how a cropped wide leg bottom works with shoes you may not expect. Like these ankle wrap sandals.

Sandals

You may think that you need a chunky heel or platform shoe with wide leg jeans to fill in the hem of the jeans, but you may be surprised by all the different slim shoes that work. I styled 39 outfits with these pants. To see a wide variety of shoes with them, read, 39 Outfits: What to Wear with Olive Green Pants.

Crop flare jeans with toe wrap Birkenstock dupes

Sometimes you need a super comfy pair of sandals for a long day of walking. Here I’m wearing tan toe-wrap Birkenstock dupe sandals with white crop flare jeans and a graphic tee shirt. 

Crop flare jeans with toe wrap Birkenstock dupes

Jeans | Sandals

This is a fresh-looking outfit for a spring or summer day of sightseeing or running around, when you want to look put together but still be comfortable.

Crop flare jeans with slides

I love an all black outfit! A column of black is very chic. Here I’m wearing a black mock-neck tee and those black crop flare jeans. With tan slides from Madewell and a matching thin belt for some visual contrast and interest.

Crop flare jeans with slides

Jeans | Sandals

Shoes that match your skin tone extend your leg line. 

Straight leg jeans with white sneakers

White leather Stan Smith sneakers work perfectly with my favorite pair of jeans, Levi’s classic straight jeans. I deliberately bought the jeans in a short length, so at 5’6” they hit just above my ankle. Since they’re dark denim with no distressing and a sewn hem, they’re jeans you can wear to work, if your dress code allows jeans.

Straight leg jeans with white sneakers

Jeans | Sneakers

These sneakers have a long footbed, which is super comfortable and lengthens your leg line.

Boyfriend jeans with white sneakers

Boyfriend jeans have a more relaxed fit all over and are cuffed, stopping at the ankle.

Boyfriend jeans with white sneakers

Gum Sole Sneakers

Here I’m wearing them with white slim Tretorn tennis shoes for a sporty look.

Crop flare jeans with black Adidas tennis shoes

Crop flare jeans with black Adidas tennis shoes

Jeans | Adidas

Here’s a sporty street look with black Adidas tennis shoes, black crop flare jeans and a simple tee. It’s elevated by the addition of a brown leather jacket. A black tote bag worn as a crossbody finishes the look. Matching your shoes to your pants or jeans is a good way to extend the look of the length of your legs. 

Straight jeans with ankle-wrap clogs

These ankle-wrap clogs give an earthy Boho vibe to whatever you pair them with. I’m wearing them with crop flare jeans and a cream embroidered Boho blouse.

Straight jeans with ankle-wrap clogs

Jeans | Clogs

The best part about wearing crop jeans is they really show off your shoes. If you were wearing these clogs with a longer pair of jeans like boot-cut jeans, it would be much harder to see the all the details on the shoes. 

I’m a fan of clogs since my hips are wider. The chunky heels balance my hips. By contrast, wearing thin heels often makes my bottom appear heavier. 

Straight jeans with cap toe flats

Cap toe flats are classics that easily work with these straight jeans. The black soft cardigan sweater worn buttoned up like a top connects to the black in the cap toe. A neutral tan bag ties in the tan of the shoes.

Straight jeans with cap toe flats

Jeans | Similar Flats

This is a great look to wear out to lunch with a friend. 

Skinny jeans with Madewell mules

These Madewell mules are my latest obsession. Madewell knows how to make pieces that look so good with denim. And these are the perfect tone of brown to pair with dark blue skinny jeans. They also look amazing with black cropped pants. 

Skinny jeans with Madewell mules

Jeans | Mules

The mules walk the line perfectly between slim and chunky with a streamlined toe and a lug sole with low stacked heel.

Here I’m deliberately wearing skinny jeans on the bottom since on top I’m wearing an oversized cropped puffer vest and white button-up blouse. The slim pants balance out the oversized tops. 

This is a great look to try if you’re wider on the bottom. Wearing slim jeans on the bottom with an oversized top is one of my favorite ways to make my wider bottom half look in proportion to my smaller top half. 

Straight jeans with chunky black loafers

These chunky black patent leather loafers were a surprise win! I never expected to love the visual interest that shiny shoes add to an outfit.

Straight jeans with chunky black loafers

Jeans (Color: Lapis Dark Horse) | Loafers

I’m wearing the loafers with my Levi’s classic straight jeans in a dark wash and black boyfriend cardigan buttoned up like a top, for a preppy look. A black belt adds definition to the waistline, as does pushing up the sleeves on the sweater. 

Straight jeans with tan loafers

Here’s another loafer look, this time with tan loafers that match the tan stripe in my button-up shirt.

Straight jeans with tan loafers

Jeans | Loafers

These straight jeans have a bit of whiskering for a more laid back feel. 

Now, let’s look at work shoes to wear with cropped jeans.

Work shoes with cropped jeans

Straight jeans with pointy-toe flats

Pointy-toe flats are perfect with cropped straight jeans. The pointy toe extends the leg line and makes them a bit more elevated than an almond-shaped flat.

Straight jeans with pointy toe flats

Jeans (Color: Lapis Dark Horse) | Pointy Toe Flats

These cropped straight jeans with their dark denim, a finished hem and zero distressing are perfect for work if your dress code allows jeans. 

Straight jeans with tassel loafer mules

These slip on tassel loafer mules have a polished look and finish that creates a preppy look with cropped jeans. 

Straight jeans with tassel loafer mules

Jeans | Similar Mules

Straight jeans with cap-toe flats

Cap-toe flats are classic and create a great look for work with straight cropped jeans. 

Straight jeans with cap toe flats

Jeans (Color: Lapis Dark Horse) | Similar Flats

They add visual interest to anything you wear with them!

Skinny jeans with black chunky loafers

My black chunky patent leather loafers are making an appearance again, this time with skinny jeans.

Skinny jeans with black chunky loafers

Loafers

Since I’m wearing a duster cardigan that has a lot of volume, I’m deliberately wearing slim fitting jeans with them. The chunky loafers offer a bit more heft, so they are proportional to the oversized cardigan.

Next let’s look at outfits for date night. It’s easy to pair your crop jeans with a shoe with a bit of a heel. 

Date night and going out shoes with cropped jeans

Straight jeans with ankle-wrap espadrilles

Here’s another shoe you can easily wear with cropped jeans. Because these jeans are short, they show off the ankle wrap on these espadrilles so you can fully appreciate how cute they are.

Straight jeans with ankle-wrap espadrilles

Jeans | Espadrille Wedges | Similar Shoes

The heel makes them date night ready. 

Straight jeans with black pointy-toe heels

Wearing black pointy-toe pumps with a heel of 3 inches with straight jeans gives an elevated feel that’s perfect for date night. The pointed toe helps to elongate the leg line.

Straight jeans with black pointy-toe heels

Jeans | Heels

I added a tweed zip jacket to elevate the look even more.

Straight jeans with brown pointy-toe heels

Here’s another look with straight jeans and brown suede pointy-toe heels. These 3-inch high heels with a pointed toe elongate the leg line similar to the look above.

camel coat outfit with jeans, white button down, and cognac colored heels

Jeans (Color: Lapis Dark Horse) | Similar Heels

These suede pumps make a simple outfit of jeans and a white button-up shirt come to life. In this outfit, the camel coat also creates a more formal and elevated feel. 

Straight jeans with platform ankle-wrap sandals

I’ve always been drawn to platform or block heel sandals over thin heeled strappy sandals. As someone who is larger on the bottom, the proportions of a more substantial heel match the proportions of my booty.

Straight jeans with platform ankle-wrap sandals

Jeans (Color: Lapis Dark Horse) | Sandals (Old)

In this look, if you’re slimmer in the hips, a pair of strappy slip on heeled sandals may suit your proportions better. These jeans come down a smidge too long, covering the top of the ankle strap on the sandal. I gave the jeans a single very slim, barely there cuff to reveal the ankle strap. 

Can you wear ankle boots with cropped jeans? 

The best part about investing in cropped jeans is that you can wear them with so many kinds of ankle boots. The boots that work with your jeans will depend on whether your jeans are tapered at the ankle or straight. Tapered jeans hug the ankle more and require an ankle boot that hugs the ankle tightly, like a sock boot. That way, the hem of the jeans will fit down over the top of the boot. If your tapered jeans are skinny jeans, a low shaft ankle bootie is easiest to style with them. Straight and crop flare jeans work with a wide variety of ankle boots. Have the hem of the pant leg stop no more than an inch or two above the top of your boot, to avoid a high water effect and keep your legs looking longer. 

Girlfriend pants with black sock boots

These particular pants are a cross between a pant and a jean with a tapered rolled cuff. They’re perfect to wear with a sock boot.

Girlfriend pants with black sock boots

Sock Booties

Sock boots have a stretchy shaft that’s very fitted around the ankle, so they fit right underneath the hem of tapered pants. Wear sock boots with any tapered crop straight jean that’s very narrow at the ankles. Tapered straight jeans are still a bit wider at the ankle than skinny jeans. 

Skinny jeans with low shaft ankle bootie

Skinny jeans are tight at the ankle, which makes it tricky to figure out how to style them with ankle boots. The easies way to wear them is with an ankle bootie that stops low down on the ankle.

Skinny jeans with low shaft ankle bootie

Jeans (Color: Lapis Dark Horse)

Here I’m wearing a pair of booties with a V-cutout that reveals the ankle. The jeans stop right at the top of the ankle.  If you’re trying to figure out how to wear skinny jeans with different styles of ankle boots, I’ve got a whole post devoted to the topic to help you out. Read, How to Wear Ankle Boots with Skinny Jeans + 8 Looks to learn more.

Straight jeans with flat ankle boots

Here’s another outfit with straight jeans and brown flat boots.

Straight jeans with flat ankle boots

Jeans | Similar Ankle Boots

The hem of the jeans fits easily down over the shaft of the boot for an easy look. Curious about how to wear different types of ankle boots with straight jeans? Read my post, How to Easily Wear Ankle Boots with Straight Leg Jeans.

Straight jeans with heeled ankle boots

Tan heeled ankle boots fit right under the hem of these straight jeans as well.

Straight jeans with heeled ankle boots

Jeans | Similar Ankle Boots

You want the hem of your jeans to come to the top of your boots or end no more than an inch or two above the top of the boots. That way, your legs look longer because your pants are longer. Plus, you avoid a high water effect.

Crop flare jeans with black platform Chelsea boots

The best part about wearing black boots with black cropped jeans is that your leg line is extended down to the tip of your shoes. If you wear black boots or black combat boots like Doc Martens that have a chunkier feel, they can shorten the look of your legs. Pairing them with black pants can make your legs look longer. 

Breton sweater, black cropped jeans, black platform Chelsea boots

Jeans | Ankle Boots

Flat chunky lug sole black Chelsea boots are very popular right now. I prefer platform Chelsea boots with a chunky heel since they give me some additional height at 5’6” tall. 

Have questions about shoes to wear with cropped jeans? Leave a comment below and I’ll do my best to answer your questions. XO, Marya

SHOP THE JEANS

Looking for more resources on wearing ankle boots with jeans? Check out my other articles on the topic:

How to Wear Ankle Boots with Skinny Jeans + 8 Looks

How to Easily Wear Ankle Boots with Straight Leg Jeans

22 Easy Outfits: How to Wear Ankle Boots Over 40

How to Wear Ankle Boots + Booties With Jeans (10 Looks)

12 Best Tips: How to Wear Socks with Ankle Boots

19 Flattering Ways to Wear Flat Ankle Boots With Jeans

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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4 Responses

  1. Great post! Do you have links and/or recommendations for the crop flare jeans you are earing in some of the photos above? So hard to find a good fit! Thank you!

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