What Shoes to Wear With Cropped Jeans

April 10, 2019

One of my most popular posts ever has been how to wear ankle boots with jeans, and I have recently posted about cropped jeans/straight leg jeans which prompted some questions about what shoes to wear with cropped jeans. It’s prime cropped jean wearing season!

I love having fun cropped jeans to wear during the spring and summer. They are cooler than skinny jeans both because of their shorter length and less tight fit. Honestly, when it comes to shoes for them, I think you can do so many things! That is the best part about cropped jeans – they are the perfect thing to show off your cute shoes. 

What Shoes to Wear With Cropped Jeans

Here’s the funny thing, I wore this outfit and put on three different shoe options intending to show you a couple dos and one don’t. I ended up liking the don’t the most of all! Just goes to show you that you can still learn something as a blogger. Taking photos of an outfit really does visually help you see what works, even if just a mirror selfie. In this case, all shoes really are options. Below I am sharing a few tips on how to make them work to your advantage though.

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Cropped Jeans Breakdown

Before we get into shoes, we have to talk about cropped jeans. The key types of cropped jeans are a cropped straight leg jean, a kick flare/demi-boot, and a culotte. In most of the photos today I am wearing a cropped straight leg pair in a boyfriend type style by Madewell. You can shop them here. Madewell is always a favorite for me in terms of denim.

Where to buy Cropped Jeans

Next, where and what brands to buy? In terms of most affordability, Old Navy offers a great line called the power straight option. My personal favorites are Levi’s and Madewell, but they tend to be my personal favorites for jeans in general (see my post about the best high waisted skinny jeans). Madewell has some really great kick flare jeans which if you have never tried on this cut/style, I highly recommend going in store and trying it before you rule it out. They are actually really flattering. They also make arguably the best, non-distressed straight jean and culotte. Their culotte is what I am wearing below. When it comes to different washes and a slightly more modern, boyfriend, broken in feel, I love Levi’s. A new fan favorite is Agolde which is what I am wearing in the photo with the purple polka dot shirt below. Find them here.

Cropped Jeans Dos and Dont’s

  • DO buy your cropped jeans where they hit a couple inches above your ankle. You want them in the area where your legs start to narrow from the calf or a little below.
  • DO NOT buy your cropped jeans were they are touching your ankle bone.
  • DO NOT buy your cropped jeans were they hit it the widest part of your calf. That is too high on your leg. You DO NOT want a capri.

Cropped Jeans with Flats

Wearing cropped jeans with flats is perhaps the easiest and most flattering way to go in my opinion. Your ankle is visible creating a clean, long leg line. There aren’t a ton of tips or dos/don’t here. If you are unsure about shoes, start with a flat or flat sandal. Sneakers count in this category too though I don’t have any photos.

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Shop My Outfit From This Post (Comment with questions about any other – they are all from previous posts. Some are pretty recent though.)


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Shop Cute Flats

Cropped Jeans with Sandals

By sandals, I mean anything that comes up on your foot but doesn’t have a true ankle strap. This is another pretty easy option to go for as far as dos and don’ts go.

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Shop Cute Sandals

Cropped Jeans with Ankle Strap Sandals

This is the trickiest of all the options in my opinion and the one I intended on giving a don’t example for in photos. In the end, I loved it! My don’t was going to be my wedge shoe below since it has a very chunky, dark ankle strap. Looking at the photos I decided it worked because you can still see enough of my ankle and foot thanks to the open footbed. There are some ankle straps I would still say are don’ts.

  • DO wear ankle strap sandals when the ankle strap is thin like my heeled black sandals in the last photo below.
  • DO wear ankle strap sandals when the ankle strap is just one strap still leaving enough of your ankle above and below the strap to show your skin. You do want a gap between your strap and the bottom of your jeans.
  • DO NOT wear a wrap style ankle strap that goes all the way up your leg hiding all your skin eliminating any leg differentiation between your shoe/ankle and your jeans. For example, I mean a sandal like this or this.

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Shop Cute Ankle Strap Sandals

Cropped Jeans with Pumps

I don’t have a great photo example of cropped jeans with a full pump, but a pump is a great option to pair with a cropped jean for a sleek and classic look. Below, you can see a mule pump with jeans and a cropped work pant with a pump for the same effect. No major don’ts here. I would avoid a chunky, platform style pump and opt for a classic and sleek pump.

Cropped Jeans with Boots

For the winter and cooler months, a boot is a great option to wear with a cropped jean. Probably the most tricky of all options, styling boots with cropped jeans can be really fun. Here are a couple things to consider.

  • DO pair a sock type boot that gets narrower at the top with a wider pant like a culotte or a straight leg jean that has enough room for it to fit under. You want the top of the boot to be narrow so that it goes under the jean. See my example below.
  • DO NOT wear a heeled, above ankle boot that does not narrow towards the top with a straight leg pair of jeans so that there is no gap between your boot top and jeans. I.e. don’t wear a tall, wide boot and have it meet at the bottom of your straight leg jeans. Your leg will appear to be one straight, wide column.
  • DO pair a short, flat ankle height boot with a cropped pair of straight/slim jeans (not culottes) leaving a small amount of skin visible between the boot top and the jean bottom. The best type boot for this is a sleek Chelsea style boot vs a chunkier style ankle boot. I don’t have a great example photo for this, but I will try to take one and add it.

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Image via Pinterest

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36 Comments

  • Reply DeAnna Sue Torrence February 20, 2020 at 7:35 am

    You don’t know how many times I’ve ended up miserable for the day, as my skinny jeans are now “bulging” up at the button, it appears like to much material, and my ankle boots, which I’m most proud and excited to wear, are now covering up my boots and I look ridiculous! Thank you for all your amazing advice! DeAnna, (continuously in need of fashion advice, midwestern girl:)

  • Reply LORENA April 23, 2019 at 10:20 am

    I have such a hard time trying to figure out what shoes to wear with cropped jeans. Great ideas.

  • Reply Jessica April 16, 2019 at 1:42 am

    Can’t go wrong with any of these, especially with the pumps. So chic dear!

    Jessica | notjessfashion.com

  • Reply Julia April 14, 2019 at 12:51 pm

    These are really great styling tips, and I love all your outfits!
    Your kimono is simply gorgeous too!
    Julia x
    https://www.thevelvetrunway.com

  • Reply Amber April 11, 2019 at 10:22 pm

    Cropped jeans are *the* pant for spring, and I’m loving all of these outfit ideas! Thank you for sharing, Amy Ann!

    I hope you are having a great week so far!

    Amber

    https://www.avecamber.com
    https://www.bloglovin.com/avecamber

  • Reply Maureen April 11, 2019 at 8:30 pm

    These are great tips Amy and you have a nice collection of both cropped pants and shoes! I, too, actually ended up liking your don’t photo. I would love to own a pair of Madewell jeans as I have heard good things about them so I have it their high waisted jeans on my wish list.

    Maureen | http://www.littlemisscasual.com

  • Reply Shea April 11, 2019 at 6:52 pm

    These are really great tips, I sometimes feel like my jeans need to be just the right length, but thinking about all the options for cropped jeans makes me realize I have more options than I thought!

  • Reply Meagan Brandon April 11, 2019 at 11:35 am

    Love all these looks and tips, although sometimes cropped jeans hit my ankle bone slightly since I’m petite 😉 The frayed hem jeans you wore in the first photos are my fave!

    Meagan
    http://www.meagansmoda.com

  • Reply Robin April 11, 2019 at 11:35 am

    I really enjoyed this post such a great idea! I also love the tips you share. I always have trouble finding crop jeans because I’m only 5’1 haha! So crop jeans typically fit me like regular jeans! Anyway, I love these you are wearing on the cover, thanks for sharing!
    -Robin
    Runwayteacher.com

  • Reply Elise April 11, 2019 at 8:26 am

    So many different styles to wear with cropped pants, and I love all of them!

    xx, Elise
    http://www.sparklendslippers,blogspot.com

  • Reply The Fashion Folks April 11, 2019 at 6:55 am

    I like all of these alternatives!! Especially wearing your cropped jeans with sandals. Love to do that! Xx

    http://www.thefashionfolks.com

  • Reply Jessica A Jannenga April 10, 2019 at 5:01 pm

    Amy, I love your style and I am thinking about a pair of cropped culottes, you wear them so well. All the jeans look great on you and I love the shoe examples you gave. You actually inspired me to go out and get more cute Spring tops this year!
    Beautiful kimono and I love it with a tank and jeans.
    jess xx
    http://www.elegantlydressedandstylish.com

  • Reply Mica April 10, 2019 at 3:26 pm

    Loving your kimono! Such a helpful guide too. Sadly, being petite, all the cropped jeans I’ve ever tried are full length on me. it does mean I save on alteration fees though, haha!

    Hope your week is going well so far 🙂 It’s a crazy busy week here!

  • Reply Rach April 10, 2019 at 2:43 pm

    Cropped jeans are seriously the best! You have the best shoe collection Amy Ann!

    http://www.rdsobsessions.com

  • Reply Rachelle April 10, 2019 at 1:58 pm

    I actually think I only have cropped jeans, great styling tips.

    xo
    Pinksole

  • Reply Lanae Bond April 10, 2019 at 1:39 pm

    You have such a fabulous shoe collection! I love how you picked the right shoes for each look.

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