Hi there and welcome! I recently picked up a pair of knit ankle pants that are already a staple in my closet. While the cold weather definitely calls for more layers of clothing, it doesn’t have to stop you from wearing ankle pants! Whether you want to style ankle pants for work, jeans that hit around your ankle, or my knit ankle pants, I put together a roundup of ways you can wear these pants in the winter.

How To Wear Ankle Pants In Winter
These outfits are all winter proof, so you can wear them when it’s cold and still stay warm!
I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.
How To Wear Ankle Pants With Flats In Winter
Knit ankle pants are a great solution to wearing ankle pants in the winter. In fact, my exact pants are literally called sweater pants. But, don’t let the name fool you! They’re incredibly stylish, and actually way more versatile than I ever expected. They’re the definition of you can dress them up or down, ha. You can wear them around the house, to work, out to run errands, or out to a nice dinner with friends. So far, I love to wear them with flats or booties, and my slippers when I’m at home! Click here to see a bunch of different ways to style these pants.

These pants come in several different colors. You can see the black pair on me here and the grey pair on me here. If you want to wear these to work, I highly recommend the black or navy.
How To Wear Ankle Pants With Booties In Winter: For The Neutral Lover
Don’t be afraid to wear booties with ankle length jeans or ankle length pants in general! You just want to make sure there isn’t a space between the top of your boots and the bottom of your jeans when you’re standing – for both a visual and to stay warm. I wear socks I like with all of these outfits, so I don’t mind if someone sees my socks when I’m sitting! I typically go with this pair, and I also wear these.

These ankle straight leg jeans feel fairly heavy, so I picked them up to wear throughout the winter and early spring. This is an easy way to wear ankle pants – with a warm sweater and booties. I’m wearing ankle boots with them here, but you can’t even tell from the photo because of how they style nicely with the jeans!
Everything I linked is exactly what I’m wearing. I wear this belt with everything because it has chocolate brown and black!
One More Outfit If You’re Wondering How To Wear Ankle Pants With Booties In Winter
These jeans are a cropped length, but you can see they still work with booties. Of course, not all booties are the same height! While the brown booties I’m wearing in the photo above are shorter than the pair I’m wearing in this outfit, they’re still not below my ankle. I would avoid super short booties and go for a pair that come up a little bit higher to cover your ankle if you want to wear booties with ankle pants. That way, your pants won’t be too short for your shoes!

This gorgeous blazer dresses up the entire outfit. You can also wear this blazer without the belt, and it looks just as chic. I highly recommend going for a monochrome look with whatever you wear under the blazer like I did. It adds to the professionalism and polished vibe that makes it all work appropriate.
The boots I linked do fit under jeans, but they are the knee high version of the ankle boots I’m wearing. I really love them because they’re super comfortable, and the knee high version was too when I tried them on. If you want to shop the ankle boot I’m wearing, this is the most similar pair by the same brand! I would go with the brown leather or wine leather if you want to wear them with the same outfit. The jeans are just this year’s version of the pair I’m wearing.
Ankle length jeans also look really nice with a big scarf (my exact wrap scarf is linked here) and a long coat if you’re wearing a classic length or long blazer like I am. You could also go for a shorter coat if you aren’t wearing such a long blazer. A blouse or sweater are both good options to wear with booties and jeans too! I typically tuck my tops in and add a belt.

How To Wear Ankle Pants To Work In Winter: Corduroy Ankle Pants
My corduroy ankle pants are under $100! They are the perfect work pants for winter, especially for casual or business casual work environments. You can wear this exact outfit below to work. If you want to dress it up, just add a nicer blazer or jacket. Denim will always make your outfit more casual, but my jacket comes in tons of different fabrics and colors. Don’t forget to layer over this look with a winter coat!


This wool sweater with the corduroy ankle pants make up an easy outfit base. You can layer over it in a lot of different ways, and you can also wear different shoes! You might notice I’m wearing the same camel sweater in this outfit as I am with the jeans and blazer above. This mockneck sweater is the perfect piece to wear all winter and spring because you can layer over it or you can wear it by itself. It has beautiful button detailing on it!
Both of the outfits from the top of the post are work appropriate too.
How To Wear Ankle Pants To Work In Winter: Dressy Work Pants
Any time I write about work pants, I always share this video because these are the most beautiful work pants I’ve ever found! They are perfectly tailored, and their length also makes them easy to wear with boots or flats. They have a 25.9 inch inseam, so they’re really the perfect length even if you’re on the shorter side like me. These pants come in lots of colors, including neutrals that are perfect for work. This is the type of pant you buy so you can wear them three times a week with different tops!
I linked several shoes I would wear with these pants when it’s cold. I would wear sock tights or socks with loafers and flats.
Okay, that’s all from me today. Did you find an outfit with ankle pants that you like? Let me know in the comments. Dresses can also be tricky to style in the winter. Click here for my blog post on how to style dresses for winter without feeling frumpy!
