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.

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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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