How to Style Cropped Pants in Winter

How To Wear A Tunic Sweater
By Jess
15 Feb 2022

As excited as I am about spring on the horizon, I’m also a realist, and I live in Vermont. It’s still February and we’ve got a ways before it’s bare ankle weather. I wrote this post on how to style cropped pants in winter a year ago and I wanted to update it again, with some fresh ideas that can take us into spring. I’ve been really enjoying getting dressed and shopping my closet. It’s a total mood booster.

I am a big fan of a cropped hemline, most of my pants hit at or above the ankle, which is great, except when it’s freezing outside and you really don’t want those poor ankles exposed to the frigid winter chill. I styled three of my favorite pants four ways in this YouTube video. Below you’ll find all of the outfit details (and the embedded video). There are so many possibilities with any of them, and I’m a big proponent of wearing white pants all year round. Do you have any other requests for styling an item? Let me know! For outfit details scroll down to the bottom of the post.

How to Style Cropped Pants in Winter

try Neutrals

You can’t go wrong with neutrals. Try whites, tans, camel tones and even light earth tones like green. I am a huge fan of white pants for winter too. No need to store them away after Labor Day!

Booties Above the Ankle

One of the key elements to wearing cropped pants in winter is pairing them with a bootie that goes above the ankle so there’s little space between your hem and the top of your boot. I like to have a little sock showing and wear ones that have cute prints.


I love monochrome looks for winter and it doesn’t have to be all white. You can for all black and add a pop of color like a fun hat or headband.

Get Cozy Socks

Sometimes I think the socks make the outfit. A little sock peaking out between your boots and hemline is super cute especially when they’re a fun print. I have too many pairs of Smartwool socks to count, they’re so cozy and comfortable for winter. Bombas has lots of cute socks too and they donate a pair for every pair purchased.

Roll Em Up

If you don’t have cropped pants or want to achieve the look with a longer pair just roll them up a little. This tends to work best with straight leg pants or jeans.

loafers and tights

I will be the first to admit that I really despise tights. So if you are on my level please disregard this advice. But I do think a pair of tights under a cropped pant with a pair of loafers is a really cute look. You can also add a cute ankle sock too.

Outfit Ideas for Cropped Pants

A White Sweater with White Cropped Pants

These are some of my favorite white pants because they’re thick but still stretchy. I paired them with my Marc Fisher boots and Sezane sweater. If I’m going out I love wearing all white with this Sezane jacket and Studio Noo bag. These Smartwool socks are some of my favorites for a “dressier” version of a winter sock. Add a little pop of color with a bright hat.

Straight Leg Crop Pant
White Button Front Sweater
Wool Coat
Chunky Teddy Mom Bag
Red Cashmere Beanie // Look for less

classic with a blue blazer and striped shirt

A classic blue blazer with stripes and white pants is an all time favorite combo. This is actually a great outfit to transition into spring, swap out loafers for warmer weather. I’d layer a camel coat over this if I were going out.

Navy Blue Blazer
Straight Leg Crop Pant
Booties (code JAK15 for 15% off)
Stripe Button Front Shirt

black jeans with green

I really like black and green together as a color combo. These jeans from Madewell are so comfy and a great length to wear with a boot that goes above the ankle like these Blundstones. This pair is actually my Mom’s but she left them at my house since she rarely wears them in California. This is a go-to outfit for mommy/daughter days because it’s comfy, practical and cute. The MZ Wallace backpack is a fave I use it for the playground/library/pool.

Harriet Sweater (code JAK15 for 15% off)
Madewell Jeans (sized down)
L.L. Bean Parka (sized down)
Blundstone Boots Dark Green (full size up)
MZ Wallace Backpack

ankle jeans and a puffy coat in shades of blue and grey

I’ve had these AG Jeans for years and it really is a testament to the quality of their denim because they are still in excellent condition. They’re one of my all time favorite pairs of jean. A no stretch denim but they have just enough give so they’re not stiff or too tight. I’m always on the hunt for a similar pair and this style looks the closest I’ve ever seen. These Bean boots are really great because you can fold them up or down depending on your pant length.

AG Isabelle Jeans
White & Warren Cashmere Travel Wrap
Cashmere Sweater (JAK10 for $10 towards your purchase)
L.L. Bean Boots (sized down)
Patagonia Down Sweater Jacket

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  1. Rach wrote:

    Honestly don’t think these photos look low quality at all! And I love that you shared this post bc I LOVE wearing cropped pants!!

    12.3.20 | Reply
    • Jess wrote:

      That’s so nice of you Rach! Thank you. xx

      12.4.20 | Reply
  2. Cathy wrote:

    Love them, and I’d wear the whole outfits head to toe! Have you tried using presets to brighten photos? I just purchased one and it’s a game changer for my insta!

    12.3.20 | Reply
    • Jess wrote:

      Yes these are edited believe it or not but the quality and lighting was bad so I couldn’t lighten them too much or they’d be super grainy.

      12.4.20 | Reply
  3. Bitsy wrote:

    Love these outfit ideas and the background looks so cozy! My favorite part of wearing a cropped, wide leg in winter is getting to put long johns underneath and not feeling like a marshmallow.

    12.3.20 | Reply
    • Jess wrote:

      Yes! They are perfect for that.

      12.4.20 | Reply
  4. Brigid wrote:

    I would wear these outfits top to toe too. They’re perfect for a north east winter.

    9.17.22 | Reply

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