How to Wear Cropped Jeans In Winter

January 22, 2020

Hi all! I have a fun new post today with this gorgeous snakeskin print kimono and fun pink top. It’s another outfit with cropped jeans which I have been wearing a lot lately. I thought it would be fun to do a post about how to wear cropped jeans in winter which mimics my posts on what shoes to wear with cropped jeans and how to wear ankle boots with straight leg jeans. I am linking those outfit details. Other outfits are linked in mentioned posts or are old.

how to wear cropped jeans in winter, how to wear cropped jeans when it's cold, straight leg jeans in winter, straight leg jeans when it's cold, what shoes to wear with cropped jeans in winter, sneakers and cropped jeans, mules and cropped jeans

Keys to Wearing Cropped Jeans

Before we go onto how to wear cropped jeans when it’s cold, I think it is best to start with some keys to wearing cropped jeans period. I did a full post about how to wear ankle boots with straight leg jeans, and I really address the things below in even more detail. I’d recommend checking it out. I have also done a summer post like this here. It addresses what shoes to wear with cropped jeans focused on warmer months.

  1. Length is key to making this look flattering! Find a jean that hits just above your ankle. I am 5’10, so to make this happen I need a longer inseam on my jeans than most. Read that part of the description when looking online for jeans taking into account your height. Not all jeans are the same.
  2. Opt for a slimmer cropped jean as opposed to a wider leg. Keeping them slim will be more flattering.

Cropped Jeans and Boots

When considering how to wear cropped jeans in the winter, boots are the most obvious choice since they are a cool weather footwear. Again, for this shoe choice I really recommend reading my post about how to wear ankle boots with straight leg jeans. It has a TON of tips in it.

Essentially you want your jeans to almost meet your boot and/or wear a sock bootie that goes under your cropped jean. Linking this new outfit below. All other clothing details for boots photos are found in my linked post above.

how to wear cropped jeans in winter, snakeskin kimono
how to wear cropped jeans when it's cold, straight leg jeans with boots and moto jacket
straight leg jeans and jacket
how to wear cropped jeans in cold months, what shoes to wear with cropped jeans

Try a Sneaker

This is also a new outfit, and I will share more on it later. Sneakers or high top sneakers are a great pairing for cropped jeans. They are more casual than boots and more comfy. The only downside is that some of your leg is exposed. If you live in a colder area of the country, you might have to wait a bit on this.

sweater and cropped jeans with sneakers

Mules/Slides and Cropped Jeans

One of my favorite shoes to wear with cropped jeans is mules or slides. They just work really well together. Again, you might have to wait on this one if you are in a colder area.

cropped jeans and mules
cropped jeans and slides, cardigan with cropped jeans

Heels and Cropped Jeans

A heel or pump is a great pairing for with cropped straight leg jeans. This is a great way to cover all your foot and dress them up. I wish I had a better photo of cropped jeans with a true pump because I love that pairing!

Tops to Wear with Cropped Jeans in Winter

When it comes to keeping cropped jeans looking flattering, you want to create a shape. Here’s my tips for tops to wear with cropped jeans.

  1. A peplum – this naturally creates a waist.
  2. Tuck in a shirt and wear a jacket or blazer over it. This is great if you want to cover your bottom and prefer a longer top. Example below.
  3. Pick a fitted top and layer a long cardigan over it. If you do this, I recommend not wearing boots as the overall look wouldn’t have much shape. Example above with the pink cardigan.
  4. Wear a sweater and do a front tuck to keep a visual waist. Example with the heart sweater.
  5. Try a cute sweatshirt with a band. Though the band comes below your jean top, it still has shape.
  6. Tunic sweaters can work IF you can still see the top of your legs/waist area. In my example with the black sweater above, my bottom is covered but the sweater doesn’t go below the start of my legs. Essentially, you don’t want the tunic to be too long. You still want to see part of your body. This is the hardest look to wear in my opinion.

Jeans I’m Wearing in This Post and/or Would Recommend

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  • Reply Jessica January 27, 2020 at 7:38 pm

    I love these, especially the heels and cropped jeans! Casual, yet sophisticated look.

    Jessica |

  • Reply Amber January 23, 2020 at 9:10 pm

    Cropped jeans and booties are my jam! Thank you for sharing these great outfit ideas, Amy Ann!

    I hope you are having a great week so far!


    Follow Avec Amber on Bloglovin

  • Reply Vaishali Verma January 23, 2020 at 11:46 am

    Loving all thse cropped jeans look.

  • Reply Elise January 23, 2020 at 8:44 am

    I am loving all of these cropped jean looks. You have styled them so many fabulous ways!

    xx, Elise

  • Reply Lizzie January 23, 2020 at 12:56 am

    These tips are super helpful! All of your outfits are amazing! So many cute winter looks!


  • Reply Cheryl Shops January 22, 2020 at 10:30 pm

    Cropped jeans and boots look so good together, and thankfully in San Francisco I can get away with exposed ankles even in winter!
    Cheryl Shops |

  • Reply Jill January 22, 2020 at 5:29 pm

    This is such a helpful post! I especially love how you paired the cropped jeans with the red heels. Such an elegant way to style jeans!


  • Reply Missy May January 22, 2020 at 3:48 pm

    Oh yes to this post and you look gorgeous in a good fitted denim jeans. Thank you for the styling tips.

  • Reply Laura Bambrick January 22, 2020 at 3:19 pm

    These are wonderful tips! You look so cute in all of these fabulous looks!

  • Reply Rach January 22, 2020 at 12:28 pm

    You have an amazing collection of jeans! These are all great outfits!

  • Reply Ashley January 22, 2020 at 11:18 am

    I live for a cropped jean- and wearing ’em with ankle boots or sock boots is my go-to when it’s too cold to have the ankles out, haha. πŸ™‚

    Le Stylo Rouge

  • Reply Kate January 22, 2020 at 9:24 am

    Loving all of these looks, especially that heart sweater <3

    Green Fashionista

  • Reply jess jannenga January 22, 2020 at 9:13 am

    All gorgeous looks Amy! I love the jeans with the ankle booties and those red heels are so eye catching. Great tips for wearing cropped denim!
    jess xx

  • Reply Midlifeandbeyond January 22, 2020 at 8:56 am

    Love all of the looks and thank you on the top tips for cropped jeans.
    Alison xx

  • Reply Jill January 22, 2020 at 8:23 am

    I love my cropped jeans and these are great tips! All of these outfits are so cute!

    Jill – Doused in Pink

  • Reply Amy Johnson January 22, 2020 at 6:56 am

    So many great looks! I love that heart sweater.

  • Reply Kelly R January 22, 2020 at 6:44 am

    As someone who is relatively petite, I love the look of cropped jeans because I feel like they are more flattering/elongating! LOVE how you styled yours–they’re perfect with booties!

    Rosy Outlook

  • Reply Meagan Brandon January 22, 2020 at 6:16 am

    Such great looks and tips, especially the one with your red mules! Giving me all the Valentine vibes!


  • Reply Rachelle January 22, 2020 at 6:14 am

    all great looks.


  • Reply Andrea Nine January 22, 2020 at 5:21 am

    I think they look great. I wear cropped jeans all winter long because I just love them, your stylings are so precious!!

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