Fall/Winter Fashion
40 Comments

How to Wear Crop Pants in the Winter

Kick flares and crop straight styles are trending this fall, and I’ve styled a few for the blog, but there is one question I always get when discussing this style . . . How do I wear crop pants in the winter?

How to Wear Crop Pants in the Winter

I get it, we usually see kick flares styled with loafers or low-shaft ankle boots that expose some skin around the ankle area, and who wants to run around in sub-freezing temperatures with their bare legs hanging out? Not me, that’s for sure!

Well, I have two words for you: Sock Bootie!

Sock booties have a higher shaft, which allows the pants to hang over them so you don’t end up with frozen ankles. They also fit close to the ankle, almost like a sock (thus the name.) This helps keep the natural shape of the leg, making the ankle area look slimmer than a typical bootie.

Mine are a couple of years old, but these are very similar. I love the cylindrical heel.

And I rounded up a bunch more below:

You can wear socks with these booties, or you don’t have to. Either way, your ankles are covered, but a knee sock will give you an extra layer of warmth when wearing crop pants in the winter.

As for my jeans, I’ve played around with some lighter washes in the past, so I styled a pair of black crop jeans for this post.

How to Wear Crop Pants in the Winter with Sock Booties

If you’re worried about crop jeans visually cutting off the leg and making you appear shorter, pairing them with a bootie in a similar or low contrast color will help create one long, lean leg line.

And of course, heels will always give you a longer, leaner look than flats.

The length of your crop pants is still important with sock booties. Just as with loafers or lower shaft booties, flared crops look best when the hem is a couple inches above the ankle bone, so they look intentionally cropped and not like you’re wearing pants that are too short. An inch can make all the difference.

How to Wear Crop Pants in the Winter

I’ve learned I need a 25″ or 26″ inseam for crop pants, especially if they have any flare to them at all. (These Mother Insiders have a 25-1/4″ inseam.)

Of course, that’s me. Every woman’s body is different, so you may have to try a few to see what works best for you.

Because cropped pants visually shorten the lower part of the body, it’s important to shorten your top to get a better balance. This also further elongates the line of the leg.

I wore this leopard sweater and gave it a front-tuck so it’s short enough to create a pleasing vertical balance.

This sweater is currently $34.50, and if you’re a J.Crew cardholder, you can get an additional 15% off that. It’s a wonderfully soft, lightweight knit that fits close to the body without being clingy. It feels much more expensive than it is, and I love this print.

If you’re not a leopard fan, it also comes in camo, floral, and several solids.

My black leather jacket is a few years old, but Nordstrom has tons of options — both genuine and faux leather.

I also added my new black belt with the silver buckle to make the outfit look more finished. For size reference, I needed a large in this belt.

The medium fit on the last notch, so I sized up to a large, which is almost too long, but preferable to barely fastening. I know I could have it shortened, but I probably won’t bother.

I completed the look with these mixed metal leaf drop earrings and a black leather satchel with silver hardware.

Crop Pants in the Winter

Outfit Details:

Mother Insider crop jeans // leopard sweater // similar leather jackets // similar sock booties // black satchel // earrings // belt

For the Pinners . . .

Did you like this post? 

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. PLUS you’ll be automatically entered for a chance to win a $100 gift card each month!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

photos: Alison Cornell

Join the Conversation

40 thoughts on “How to Wear Crop Pants in the Winter

  1. OH, THANK YOU!

    You know I’ve pestered you with sock questions before!  This outfit is gorgeous on you…SO stylish and you look amazing.  Well done!

    I would try to pull off this look, although I would be less likely to do it with jeans.  I think I’ve aged out of that option.  The images in your boots/jeans widgets seem a little too fashionable to work for me.

    We’re in a northern climate VERY well known for snow.  But this is a fun look for fall and no-snow days.

  2. This is so helpful.  I was just struggling with how to wear this style.  I like the look of the sock bootie and combined with knee socks  will make it warm as well.  It seems like tucking the shirt in is a must with this style of pants.  

    Thank you! 

  3. Great, informative post! And that outfit is so🔥 on you! I never thought I’d be tucking shirts in again, but I’ve found that, as you said, it really creates balance in your proportions. I’m not much of a belt girl so I just blouse it a bit to cover an inconspicuous belt. And I think I’m getting on the sock bootie train too. Tres chic!

  4. You look fabulous in this beautiful outfit, Jo-Lynne!  I am happy to report that we have finally had some rain, and we have more moving in.  The farmers down here need it so bad, as well as the lakes,rivers, etc.  Have a great day!

  5. Wow, you nailed this look, Jo-Lynne! I was considering sitting out this trend but now you have me curious to try it. Happy Thanksgiving to my fellow Canadians!

  6. Ohhh I dread this new style. Just cannot get over it looking like “high waters”. Probably dating myself with that comment, but that is all I can think of! You look very nice in them but I feel like it is a look that only certain body types can pull off.

      1. Me too Jenny! I think that is probably why I don’t like it. I feel like it chops my leg and makes me look frumpy:(

  7. Great post – I just received that top in leopard print two days ago from JCrew, and I love it! Fabric is soft and not too thick or thin to wear under a sweater, jacket, or coat (it is TTS in small for me based on size chart). I’ll wear it with straight leg, regular length black jeans or black skinny jeans and RL Welford boots since the cropped don’t work as well for me in the look.

  8. I just can’t see how cutting your leg off like this is a good thing, especially for those of us with short legs to begin with.  The “What Not to Wear” people’s voices still ring in my head, saying that your pants should almost graze the ground to elongate the leg.  They must have sold me, because I can’t get away from it. Haha

  9. This look is terrific on you….. On me, probably not so terrific. I agree with the other comment about “What not to wear” with pants needing to be being longer to look more slimming and flattering. I’d look like Erkle from Family Matters (now I’m really dating myself!😀)
    Happy Thanksgiving to your other Canadian readers.

  10. While this outfit looks absolutely stunning on you, I just haven’t seen this style pant take off here… Happy Thanksgiving to fellow Canadian followers and Happy Columbus Day to you.

    1. Here either, lol. At least, not out here in the burbs. I did notice some of them when I’m at the mall closer to Philly. It’s fun to be a little ahead of the trends. 🙂

  11. Ahhh You figured out the formula. Lol  You look very stylish today. Everything about your outfit is bang on!  My takeaway is to make sure the pants hit at the right spot on your legs, wear a heel & tuck your top to balance the shorter bottoms. I might get on this trend yet. I’m usually slow to a trend and adopt it just as it’s going out. 😜

  12. Love the boots, but I can’t find any with a heel shorter than 3 inches. I need a pair with a 2.5 inch heel.

  13. I’m a 62 year old woman (with a 24 year old daughter) and she looks phenomenal in this look! I purchased sock booties at the Nordstrom Anniversary Sale as well cropped jeans on her recommendation.  I feel very stylish in this look now and I think you rock it as well!

Want More?