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 . . .

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photos: Alison Cornell