How to Style Cropped Pants in Winter

Can we call this low quality photos, high quality fashion? Eeeek, I’m sorry these photos are pretty brutal but I have to make do with nap time as my short window to work and my phone is the easiest and quickest solution. This house is pretty dark too and I don’t have lighting here, anyhoo I digress. When cold weather rolls around I get lots of questions about how to style cropped pants in winter. Specifically how to style something other than leggings with booties.

I am a big fan of a cropped hemline, pretty much all 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 chose these three pairs of pants/jeans because all the items in the photos above are basically interchangeable with one another. There are so many outfit possibilities with any of them, and the boots work with each pair of pants/jeans as well. Make sure you check out my Reel to see how I put together each outfit. 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, just one I will not do because tights are so uncomfortable, but maybe it’s just me. You can also add a cute ankle sock too.

Outfit Ideas for Cropped Pants

A White Sweater with White Cropped Wide Leg Pants

I wish I had taken the coat off for the photo (but you can see the sweater in the Reel HERE). I love a chunky white knit sweater with white pants. Then I paired them with my Blundstone boots and a cashmere scarf. I like that the hem of the pants hits right around the top of the boot. I don’t mind a little sock showing, especially in a cute print. For winter I like anything merino wool.

Stand Studio Coat (size 34), also available in this color
Long Wharf Supply Rye SeaThread Sweater (small – buy any 3 sweaters get 20% off through 12/6 no code needed!)
Anthropologie Wide Leg Pants (old, similar here)
White & Warren Travel Wrap (grey heather) – Use code JESS20 at checkout for 20% off!
Mate the Label Thermal (Medium)
Blundstone Boots (went up a full size)
Pendleton Camp Sock
Rhinestone Headband

Cropped Jeans with Neutrals

Again I wish I took a photo without the coat so you can see how I layered (check out the video to see the full outfit). A go-to combo for me is cropped jeans with a neutral sweater and tan booties. I layered a silk cami underneath a cashmere cardigan, a great holiday at home outfit. And if you’re not leaving the house just rock it with your coziest slippers.

Stand Studio Coat
Vince Cropped Jeans (via thredUP)
Paige Silk Camisole
White & Warren Cashmere Cardigan (old, similar here)
Dolce Vita Coltyn Booties
Eileen Fisher Cashmere Scarf
Pendleton Camp Sock

all black with a pop of color

I really like this all black outfit because there’s subtle pops of color and the shiny puffer coat breaks it up a bit. There’s a super subtle red in this plaid blanket shirt so I paired this outfit with my red cashmere beanie to tie it all together. It might seem bold to wear a bright red hat but I actually get so much wear out of this beanie. Especially for winter it is so festive for the holidays, and it’s really warm.

Patagonia Raven Rocks Jacket (M)
Outerknown Blanket Shirt (xs/s)
Reformation Jeans (via thredUPthis style)
Dolce Vita Booties (old, similar)
White & Warren Cashmere BeanieUse code JESS20 at checkout for 20% off!
Splendid Turtleneck
Smartwool Mini Boot Socks

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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