Fall/Winter Fashion
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How to Wear Ankle Boots in the Winter

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.

How to Wear Ankle Boots in the Winter  Mother Tomcat straight ankle jeans (29) // similar Aquatalia weatherproof boots // J.Crew cocoon coat (6; 50% off) // Burberry scarf (budget option)

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

Marc Fisher booties (8; 50% off) // Frame Le High Straight Ankle Jeans (28) // Kate Spade shoulder bag (60% off!) // No Show Boot Socks

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.

Marc Fisher booties (8) // Frame Le High Straight Ankle Jeans (28) // old cable knit sweater (S) // Sam Edelman Reefer Coat (50% off)

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.

Madewell cardigan (S; extra 50% off with TGIF) // Frame Le High Straight Ankle Jeans (28) // rag & bone booties

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.

similar Mother Insiders // similar booties // Caslon cardigan & tee

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.

AG Farrah ankle skinny jeans // Marc Fisher Yale Chelsea Boots (size 8; 25% off) // Smartwool socks

#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.

Sorel Explorer Joan (size 8.5; 25% off) // similar skinny jeans // The North Face parka

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.

UGG Adirondack Boots (9) // Fidelity Cher (similar style in stock) // Equipment sweater (S) // old puffer vest

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.

Sam Edelman Elsy Brown High Heel Tall Boots // AG Farrah Ankle Skinny Jeans

#3. Wear Your Jeans Over Your Boots

Vince Brannen Booties (8; 40% off + 25% off with code BLACKFRI) // similar coated bootcut jeans (29)

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.

Vince Brannen Booties (8; 40% off + 25% off with code BLACKFRI) // similar coated bootcut jeans (29) // Vince cardigan (S; 60% off) // Marc Jacobs hobo // rag & bone sunnies

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.

KUT from the Kloth jeans (6; 10% off) // Dolce Vita Volli boots (8; 65% off!!!)

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!

KUT from the Kloth jeans (6; 10% off) // Dolce Vita Volli boots (8; 65% off!!!) // fair isle sweater (S; 10% off) // Kendra Scott earrings // YSL Lou (similar for less)

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.

Aquatalia Brigitte (50% off; 8.5) // Mother Hustler ankle flares (28; 30% off) // Jenni Kayne sweater (S; 25% off) // J.Crew vest (S; 50% off)

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 (50% off; 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.

Aquatalia Brigitte (50% off; 8.5) // Frame Le High Straight Ankle Jeans (29) // Burberry scarf (budget option) // similar jacket

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.

 KUT from the Kloth corduroy flares (6; 25% off) // Sam Edelman Agnes Western Boots (8; 33% off) // funnel neck sweater (S; 20% off)

The Sam Edelman Agnes Western Boots have a 7″ high shaft, so they also work well under shorter jeans, like these straight ankle jeans.

Paige Cindy Straight Ankle Jeans (29) // Sam Edelman Agnes Western Boots (8; 33% off) //  Treasure & Bond V-Neck Sweater (S; 40% off)

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.

 Mother Tomcat straight ankle jeans (29) // similar Aquatalia weatherproof boots // J.Crew cocoon coat (6; 50% off) // Burberry scarf (budget option)

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!

Vuori Cozy Sherpa Jacket c/o (size S) // Sorel Explorer Joan (size 8.5; 25% off!)

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.

outfit details

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.

similar Aquatalia weatherproof boots // Good American skinny jeans (6) // faux leather puffer (S; 30% off)

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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44 thoughts on “How to Wear Ankle Boots in the Winter

  1. Thank you! I struggled with this as I was getting ready this morning. Could not decide so I ended up going with my flat loafers. But it’s 21 degrees in Minnesota this morning, so this is not really an option anymore! I have to admit, I am happy to see socks making a comeback!

  2. Thank you for this post, so helpful! You linked the UGG Adirondack III Waterproof Booties – what color/size did you end up getting?

    1. I literally just ordered them as I was writing this post yesterday. My mom has a pair and I love them – so lightweight and WARM. I went with the 9, b/c it says to size up, and she usually wears 9 1/2 and has a 10.

  3. I am seriously struggling with this right now. At 5’8″, most of the ankle length jeans you feature look like a crop jean on me. My ankle boots are too short, and I still have riding boots! I need a major wardrobe overhaul. Can you recommend any slim straight-style jeans with 30″ to 32″ inseam? They are hard to find.

      1. Thank you! I’ve owned that particular style of NMDJ’s. The length is great!! But they stretch out soooo much, so I’ve been looking for alternatives. I appreciate the recommendations!

      2. Thanks for this list.I’ll be checking them out as well. 5’8” is such a hard height because the regular length pants are too short but talls are often like 4 inches longer and therefore too long!

    1. Check out Buckle jeans as they carry tall jeans & you can buy by the length. A bit pricey but so worth it. Some tips, hang dry them & wash inside out, & of course get a few days off wear or off them before you do wash if they aren’t dirty. Many people do this to make their jeans last longer.

  4. This is my favorite kind of post, the “how-to.”

    I just received the Joe’s Jeans coated jeans shown in #3. Love! Very long on my 5’4″ body so they are getting hemmed. I really love them–legs for days and very elegant.

  5. I still struggle with snow boots and jeans because I live in a cold climate like you. Snow boots are a necessity, All the heeled boots are great for going out but what to pair together when you’re running errands, grocery shopping—— just everyday stuff. Heeled boots are not as comfortable for hours when you’re running errands. There must be some options with snow boots and jeans other than skinny jeans?? Maybe leggings?? I’m at a lost. Please help.

    1. I’ll play around with mine when I get home. I plan to wear straight ankle jeans and cuff plus socks. But I need to see how that works with the styles I have in my closet. I have the Sorel Explorer and I just ordered the UGG Adirondack.

  6. Do you own the Marc Fisher booties? They look like leather but the website states suede, which they do have in other colors. Are they leather or man-made material? Do you own the black Talbots booties you showed the other day and if so, can you compare the two pairs, thank you,

    1. Which Marc Fisher booties? I own both the black leather pair and Cloud Suede pair. My leather pair is the Yale – the pair at Macys is similar. I didn’t look closely at materials.

      And which Talbots booties? I have the Talbots knee high wedge boots.

  7. I can’t find the link of the UGG boots you just ordered like your moms. Could you send please? I’m really interested. I want to get new snow boots this Winter and waiting for a post? I love Sorel too, but haven’t had a pair before.

  8. So I have great leather riding boots. I know the flat heel is not in style now. Should I just tuck them away waiting for them to come back in style?

    1. So I’m going to chime in here and agree with Jo-Lynne and say YES- hold onto those riding boots! Just because the latest TikTok videos aren’t showing them right now doesn’t mean they’re “out” or that we can’t wear them. Plus….it’s all in how you style them to keep your look fresh and current IMO. I never wear heels higher than 2” anymore and riding boots are perfect for me personally because I can wear them with dresses or skinnier pants/jeans. (I don’t feel like I look dated when I go out.) And for what it’s worth, I live in a pretty fashionable area of So Ca and I’m seeing many women wearing tall boots over jeans and black pants right now.

      1. ditto to the riding boots, I have Frye riding boots and they’re not going anywhere. I have a couple of other styles by them and to me they’re the best wearing ever, too expensive to replace. I also do not wear anything other than a very low heel.

  9. Looking forward to seeing how you style the new UGG boots you just ordered. I live in Ohio and have pretty much the same weather you do and I too struggle wearing winter/snow boots. I own NO skinny jeans (never ever liked them to begin with). Most of my jeans are the Mother cropped jeans and I typically wear a loafer when I am going into the office or a tall shaft bootie. When it’s snowing, I have some Merrell Alpine sneakers I wear the cropped jeans; however, not really ideal for alot of snow. Thank you for the ideas.

  10. Fashion is so fickle! Funny how what we turned our noses up at just a couple years ago is now trending. And vice versa! I’m interested in your take on this. If you live in an area that’s not as fashion forward (the trends do come just not as quickly!) do you think it’s ok to slowly incorporate new trends while keeping one or two pieces in the older trends?
    For example, I’m slowly replacing my skinny jeans with straight and bootcut. However I’ve kept one skinny pair. I still have a pair of riding boots that are fur lined and by far my warmest pair (we don’t get much cold weather). I wore them this week during a frigid snap, even though I know that look is dated.
    For most of us, we can’t afford to replace all our jeans and boots every time the trends change. So how do you feel is the best way to gradually phase it in?

    1. Yes, fashion IS fickle, but it doesn’t change as fast as it may seem. With social media, it may feel like a drastic shift when the fringe trends are hitting the mainstream, but trends exist on a spectrum, and pant silhouettes have been changing for quite a while. So yes, absolutely, most people gradually introduce the newer trends as they phase out the old. I think it just happens at different rates and at different points as they start to notice the evolving styles.

      1. Agreed. My other question (back to my boot dilemma this week) is what options do we have with the new jean styles when it’s too cold out for ankle boots and we want to wear knee high ones? Back in the day I tucked knee high boots under my flares, but they were those skin tight “pleather” things with no structure (cringe!). Most of the taller boots now, especially the lined ones, are too bulky to make this work. Thankfully we don’t get enough cold weather here in the South for this to come up often, so I’m hoping you can tell me the northern girl tips!

        1. I don’t remember wearing knee high boot under my bootcut jeans. I lived in bootcut jeans in the early aughts, when my kids were young. I remember wearing ankle boots with them, usually with a bit of a heel, all the time as a young stay at home mom. I never wore sneakers with them, I had a friend who did, and I remember thinking she looked frumpy, lol. I guess I wore wedge sandals in summer. I need to look back at those pix – I am sure I wore them sometimes with snowboots. I mean, it’s Philly. But I can’t recall which boots and how I wore them with the jeans, I guess with the jeans over top.

  11. Loved the post! Very helpful!
    I am wondering, is the YSL Lou bag you are carrying in the post a dark tan or taupe? The Saks site offers both. Very confusing. In my mind taupe is dark tan.

  12. For those of us unable to wear heals the riding boots with skirts and leggings underneath are the best way to stay warm and ladylike!!!

  13. Hello, I live in Wisconsin & cold weather has set in. I have 2 solid color (tan & dark green) midi skirts with enough fabric weight; I can wear them this winter. What type & color of leggings do you suggest? I do have a pair of tan bootie shoes. Thank you very much. Sue

    1. With tan booties, I’d wear tan or ivory leggings with the tan skirt for sure, and probably also with the green. Typically you match the skirt or the shoe, but if the shoes are light, I usually go with the lighter shade on the legs.

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