How to wear ankle boots in the winter is probably THE most requested topic I get this time of year, and I’m getting it now more than ever due to the changing denim and pant styles this season.
This question usually comes up because women have been wearing ankle boots sans socks with crop and ankle-length jeans for the past few months while the weather has been mild, and now they’re wondering how to wear their favorite ankle boots without freezing in these frigid temperatures. For that reason, this post will be focused around how to wear ankle boots with jeans in the winter.
How to Wear Ankle Boots in the Winter
When wearing ankle boots with jeans, you really only have three options. You can wear your jeans down over top of your boots, tuck your jeans into your boots, or wear jeans that end above your boots with some sock or skin showing.
From there, it takes some trial and error to figure out which boots and jeans work best together based on the length and width of your jeans and the height and width of the boot shaft, but those are really your only three options. Let’s discuss!
#1. Show Sock or Skin
You can certainly continue to wear your ankle boots with crop and ankle length jeans and pants and allow a sliver of skin to show. Even living in Philly, I occasionally go out and about with bare ankles in the winter months on milder days.
The good news is, you can wear this look with skinny jeans, straight leg jeans, or flares. If your jeans aren’t the right length for this look, you can cuff or cut them to the desired length.
I would prefer to see these jeans about a half inch shorter with these boots, but a cuff didn’t work well with the raw hem, and I didn’t want to cut them because this length looks good with many of my other shoes, so I just wore them this way.
It works because the hem of the jeans just meets the top of the boot. What you don’t want to see is the jeans getting hung up on top of the boot.
Here is an outfit with the same jeans and a lower shaft bootie that shows just a hint of skin, but the bootie with the dip in the front looks dated to me, so I kept them to wear with longer flares that cover the top of the bootie. I also wouldn’t wear socks with this outfit.
Here’s a look I love with crop flares. These boots are old, so I linked a similar style. Boots with side cut-outs like these are intended to be worn without socks, so this is definitely a look for milder winter weather.
Keep in mind, perforated booties and boots with low cut-outs are not supposed to be worn with socks that show. If you want to wear a sock that doesn’t show in your ankle boots, these Sheec No Show Ankle Boot Socks are your best bet.
If You Want to Show Your Socks…
You can wear socks that show between the hem of your jeans and the top of the boot shaft, as long as it looks intentional. Choose a sock that coordinates with your outfit, or even a pair that stands out in some way if that aligns with your personal style.
I like how these Smartwool socks have a pattern to them, but they maintain the monochromatic grey and black color palette from the outfit.
#2. Tuck Your Jeans Into Your Boots
This pretty much only works with skinny jeans, and the ankle boots have to have a shaft that is wide enough and high enough to accommodate the jeans. There are some mid-calf boots that you can wear this way as well.
I don’t really wear skinny jeans much anymore, but I kept a pair in my closet for wearing with snow boots this winter.
This can actually work with slim straight leg jeans as well. I did some experimenting with my new UGG Adirondack boots. They can be worn with the top turned down with the shearling cuff showing, or you can unfold them and wear them taller. I like them both ways with these Fidelity Cher slim straight leg ankle jeans.
I realize this post is about ankle boots, but if you like wearing taller boots over skinny jeans, I’d steer clear of the riding boots over skinny jean look we were doing 5 – 7 years ago.
A more current look would be a heeled fashion boot like this, but I have to say, I’m not really feeling this look at all right now. I think there are more relevant ways to stay warm… which brings me to option #3.
#3. Wear Your Jeans Over Your Boots
This works best with full length pants and jeans, but it also works with crop and ankle length styles as long as the boot shaft is tall enough and narrow enough to fit easily under the pants.
With Bootcut & Flare Jeans
Full length bootcut jeans will fit over almost any ankle boot. These almond toe block heel fashion boots are practically made for bootcut jeans. You can wear any socks you want because no one will see them, and the lower shaft isn’t an issue since the jeans are so long.
The main thing to note here is, you want to make sure your jeans are hemmed to the right length.
Style Tip: Full length bootcut pants should end 1/4″ – 1/2″ above the ground in the back with shoes on.
With Crop & Ankle Length Jeans
When wearing ankle length or crop jeans, boots with a higher boot shaft work best so the hem of your jeans doesn’t get hunt up on the top of the boots when you sit down and stand up again. And if your jeans are more of a slim cut straight, booties with a slimmer shaft will work best here.
These booties have a narrow 5″ shaft, so they slip right under these slim straight leg ankle-length jeans. These jeans and these booties are a great pairing, both color and style-wise, so I will be wearing this combo a lot this fall and winter!
YOU MIGHT ALSO LIKE: How to Wear Ankle Boots with Straight Leg Jeans
These ankle flares are a wider style, so they can accommodate a bootie with a slightly wider shaft, like this Aquatalia pair. And these boots have a 6″ shaft, which is a little higher than most, which works best with shorter jeans.
Here’s a better look at these Aquatalia boots. Aquatalia boots are spendy, but they are made for cold and inclement winter weather, without looking like it. I always buy mine on sale, usually at the Nordstrom Anniversary Sale, and sometimes you can find good deals on them at Nordstrom Rack and Saks OFF 5TH.
Aquatalia Brigitte (8.5)
I’m in Maine right now, and it is freeeeeezing. I wore these boots because they’re weather resistant and also warmer than most fashion booties. I wore my J.Crew cashmere crew socks inside, and my feet are toasty warm.
FYI, these socks are 50% off! They make great gifts, or treat yourself! I’ve also been wearing these around the house because I didn’t have room to pack slippers in my carry-on.
This is definitely my favorite way to wear ankle booties right now. Here are some more looks I’ve styled recently wearing my jeans and pants over my ankle boots.
The Sam Edelman Agnes Western Boots have a 7″ high shaft, so they also work well under shorter jeans, like these straight ankle jeans.
I mentioned Aquatalia boots above, this is a black pair I’ve had for a few years. Again, these fashion boots are also weather resistant, so you can wear them in icky winter weather and still look chic and stylish.
Of course, sometimes you just need to wear a true winter boot. One of my favorites is the Sorel Explorer Joan, so I dug them out of my basement and started playing around with them. I discovered they actually fit under my straight ankle jeans and look pretty good this way!
If you like the lug sole Chelsea boots, they look great with a straight leg jean cuffed like this. I asked my friend Dawn if I could borrow this picture because I love this look.
With Skinny Jeans
You can even wear skinny jeans over top of ankle boots if the boot shaft is very narrow; sock boots work best.
I hope this post is helpful as you figure out how to wear ankle boots in the winter in a way that pleases you! Because we all have different body types and style preferences, every woman has to do her own trial-and-error experiments to figure out what looks best to her, but this post should give you a place to start!
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