Fall/Winter Fashion
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How to Wear Ankle Boots {2020}

This post on how to wear ankle boots is one of my most popular, and it was most recently updated in January of 2020!

There are soooo many styles of ankle boots and so many styles of jeans that it is a bit of a sticky wicket, figuring out how to style your ankle boots, so I’m here to help!

I’m sharing 5 ways to wear ankle boots in this post, along with pictures and explanations. First we’ll talk about how to style ankle boots with various types of jeans, and then I will touch on dresses and skirts at the end. I hope it’s helpful.

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Okay, so back to ankle boots… These pictures are meant to be examples so you can come up with similar combinations from your own closet, but I do link to the items shown (or similar if they’re old.) But by all means, shop your closet or your favorite retailers for similar styles if some of my examples are out of budget.

HINT: Click on any picture below to see a full post on the look.

How to Wear Ankle Boots with Skinny Jeans

Generally, boots with a taller shaft look best with skinny jeans tucked in, and boots with a lower shaft look better with jeans untucked or cuffed. Let’s break it down.

#1. Tucked Into Skinny Jeans 

For a long, lean line, tuck the pants into the boots. This works best with legging jeans where the leg opening at the ankle is small and they fit snug to the leg. You don’t want them to look bunchy. If they’re going to bunch, you’re better off cuffing them. (See #2.)

How to wear ankle boots with skinny jeans tucked in.

ivory turtlenecks // wool reefer // similar scarf // skinny jeans (option) // similar booties  // leopard clutch

#2. Untucked with Skinny Jeans

This is when you really have to experiment with the style of bootie and the length of your jeans to see what works best.

Cuff or double-roll your skinny jeans allow a hint of ankle to show. This works best with ankle-length skinny jeans. If the jeans are super long, there is a larger cuff, which can work, but it can also cut off the leg line in an awkward way, so it takes some trial and error to decide what works best for every combination of jeans and booties.

sweater // skinny jeans // boots (more sizes) // earrings

This works because it makes the ankle look slimmer. Generally you want a bit of your skin to show because this is the narrowest part of your leg, and showing some skin helps prevent your legs from looking stumpy. Sometimes mine end up on the top of the boot as I walk around and my pants settle, but that’s okay.

I feel like the single cuff is more current at the moment. I’m seeing it more than the double, but sometimes it depends on the length of pant, as well as the length of your top. If your top is shorter, you can afford to “shorten” the leg-line with a larger cuff. If your top is longer, you want to keep the line of the leg as long as possible.

Here’s another similar example with white jeans and cognac booties.

white skinnies // similar booties

You can also just let your jeans fall to the top of the boot and bunch or rest on top. This works best with lower shaft booties.

puffer vests // grey turtlenecks // black jeans (option) // similar booties

In the next example, these jeans with the split hem don’t really allow cuffing, so again, I paired them with a lower shaft bootie — you can see that I let them fall into the back of the bootie, but in front, there is some skin showing between the hem of the jeans and the top of the bootie.

Jo-Lynne Shane wearing AG The Legging Ripped Ankle Skinny Jeans, Jeffrey Campbell Vanhook booties, Rails plaid shirt #Nsale 2018

plaid shirt (Ivory Bluebell Pink) // jeans // taupe booties

Here’s another example with the same booties:

jacket //  blouse // skinny jeans (option) // booties

Whether or not you cuff your jeans depends on the length of your jeans, how snug they are to your ankle, the height and style of your boots, and yes, even your top! I KNOW! So many variables. This is why it’s important to try them different ways in front of your full-length mirror until you find the perfect combination.

And here’s yet another option . . .

Leave them out over top of sock booties or any bootie with a taller, narrow shaft.

I often wear my black sock booties with black ankle skinny jeans for a long, lean leg line.

Jo-Lynne Shane wearing AG black the legging ankle jeans, Everlane the cashmere v-neck, Everlane day market tote, Club Monaco sock booties

v-neck sweater // black skinnies // similar style bootie // tote

#3. With Straight Leg Jeans

Straight leg jeans are trending, particularly the cropped styles. The good news is, these styles look great with ankle boots! And you don’t have to work quite as hard to find the right combination of length of jeans and height of boot shafts.

When wearing straight leg jeans with ankle boots, try to achieve one long, lean leg line.

To do this you may need to allow the hem of the jeans (whether cuffed or un cuffed) extend over the shaft of the boot so they don’t cut off your leg and make it look stumpy. Here is an example of how I styled a slim straight ankle length jean with suede block heel booties.

mock neck sweaters // straight ankle jeans // similar booties // bag

Because I haven’t experimented a ton with this look, I’m going to share a few other examples from the Nordstrom website. But first, a caveat. Do not rely on retail websites to show the proper styling of boots and jeans. Most models are super tall, and they generally don’t alter clothes to fit them properly when shooting looks for the website pictures, so I find a lot of times denim lengths are off. However, I found a couple examples that I believe got it right.

In this example, there is a little bit of skin showing between the hem of the jeans and the top of the ankle boots — this works, but you don’t want them to be any further apart, or it will chop up the line of the leg too much. (Here is an example I think shows too much space between the jean and the boots.)

Also, because there is low contrast between the light wash denim, the pale skin of the model, and the white bootie, you get a long, clean leg line even though it’s chopped up by the jeans and boots being separated.

straight leg jeans // similar white ankle boots

In this next example, the hem of the jeans extends over the shaft of the ankle boot by about an inch, allowing for a smooth transition, even though there is high contrast between the mid-wash denim and the black booties.

This works without shortening the line of the leg too much, especially because the higher rise extends the jeans a couple inches at the top, compensating for the shorter leg length. It’s all about balancing the proportions! This is why it works best to wear a cropped top or to just tuck in the top when wearing cropped jeans.

I think this look also works well because the high-heeled, pointy-toe ankle boot is slimming and helps to visually lengthen the line of the leg. A flat boot might not work as well.

high waist ankle straight leg jeans // similar ankle boots

Sock booties also work great with the straight ankle and straight crop jeans that are trending. Here is an outfit with the same jeans as above, but with black sock booties, a grey sweater, and black leather jacket.

Jo-Lynne Shane wearing Frame Le Slender Straight ankle jeans with Club Monaco black sock booties, Vince crewneck cashmere sweater, and Bernardo leather jacket

grey sweaters // leather jackets // straight ankle jeans // similar booties

Here’s another example with sock booties and black crop straight jeans . . . the jeans extend over the top of the bootie, creating one long, lean leg line. Again, I front-tucked my top to compensate for the shorter pant.

 leopard sweater // black jeans // similar leather jacket // similar booties // black satchel // belt

#4. With Boot Cut Jeans

Bootcut jeans are trying to make a come-back, in both cropped and full-length styles, and the best part is, they are pretty much universally flattering — especially if you’re trying to balance out wider hips or a larger upper body.

The most important factor when wearing ankle boots with bootcut jeans is the length of the jeans. When pairing shoes with bootcut jeans (any shoe – not just ankle boots) the hem of the jeans should come within an inch of the ground without touching the ground. I prefer mine closer to 1/2 inch from the ground. I also think bootcut jeans look best with a pointy-toe boot or shoe because it elongates the leg, but you can wear them with a rounded toe if you prefer. I also prefer my bootcut jeans with heels, but again, flats are an option, but in that case a pointy toe definitely helps.

Again, don’t rely on retail websites to show the right length. Often the models wearing the jeans are too tall for the jeans they are modeling, but I rounded up an example that I think got it right. Of course they are showing them with pumps, but they should look the same with booties.

The proper length for boot-cut jeans and more style advice for women over 40 at jolynneshane.com!

Joe’s Curvy Bootcut Jeans

Here’s an example of how I wear mine.

How to wear bootcut jeans with ankle boots for 2017

floral blouse options // bootcut jeans  // similar booties

When pairing ankle boots with cropped bootcut jeans, the rules for the straight crop jeans apply. I’m not seeing these as much these days — the straight crop look seems to be more popular.

#5. With Leggings

Ankle boots can look really chic with leggings — especially faux leather leggings for a dressier look.

Here’s a holiday look with faux leather/ponte leggings, a turtleneck tunic sweater, and black suede ankle boots. In this case, the leggings just meet at the top of the ankle boots, but it’s okay if the ankle boots come up over the leggings too.

#6. With dresses and skirts

Ankle boots are a great way to update a classic skirt outfit. To keep a long, lean line, go for a monochromatic look. Here’s an example from Pinterest of a black skirt, black tights, and black ankle boots.

how to wear ankle boots with a skirt and tights

If you like to go bare and worry about chopping up the line of the leg too much, stick with ankle boots that are close to the color of your skin so your legs don’t look chopped off at the ankle. I tried this look with a denim skirt and really liked it.

These taupe booties are close to the color of my skin so they don’t chop up the leg too much. Also, the shaft is high and rather narrow, keeping my ankles looking slim, so they work well with skirts and dresses.

How to wear a denim skirt with ankle boots

denim pencil skirts // stripe v-neck tees // taupe booties // crossbody // leather jackets

Sock booties are also trending right now, and they work great with dresses. Here’s how I wore mine with a black shift dress. In theory, these chop up the line of the leg, but somehow the proportions seem to work because the dress is shorter, showing more leg.

how to wear sock booties with a dress

black bell sleeve dresses // similar booties // leopard clutch

Figuring out how to wear ankle boots can be challenging, but once you get used to them, I think you’ll find that they’re quite versatile.

Play around with them, and don’t be afraid to try something new!

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54 thoughts on “How to Wear Ankle Boots {2020}

  1. I love hearing that!!!! It’s harder and harder to “get found” these days with so many blogs. So glad to hear people are still finding me via Google and sticking around. 🙂

  2. Even though I don’t wear boots, I found the content of this post to be very informative and helpful.  While I still like my skinny jeans, the one thing that does aggravate me, is that they don’t stay in place on my legs.  The bunching up drives me 🥜!  I hope you and the girls thoroughly enjoy your final week of summer break.  Oh, I’m glad Paul was happy about you organizing his closet for him.  Have an awesome day!

  3. Excellent post, Jo-Lynne!  So informative with great examples, and up to the minute good advice!  I have this post saved under my favorites, and refer back to this post at the start of each “boot season”.  Thank you for your work to keep the rest of us attire appropriate and fashionable!!  Can’t wait to start wearing boots again!

  4. Great post and helpful tips! Thanks for helping us navigate booties with different types of jeans. Enjoy your week and pool! The smoke is so oppressive out west from the hundreds of forest fires. Really looking forward to seeing blue skies again come fall. It feels apocalyptic here.

  5. This was so helpful as I purchased my first pair of ankle boots a few weeks ago. I was wondering what type of socks you wear with these if they show a good amount of your foot.

    Thanks so much and enjoy your week!

    1. I don’t usually wear socks in the fall, but I have these that I wear with Converse, and they would work under the ankle boots with the lower shafts: https://rstyle.me/n/c79pjdgthw

      When it gets cold, sometimes skip the ankle boots in favor of knee-high or over the knee boots, or I wear trouser socks with the taller ankle boots, when my jeans cover them.

      1. So there’s no acceptable sock other than a no show? I really hate those things. I usually wear ankle socks or cuffed ones. But idk how to fix this with my new ankle boots!

        1. It depends on the bootie. Those with the split shaft, I wouldn’t wear with socks that show. But other booties, I do. I just try to match the sock to the bootie or the jeans – or get close. I don’t have a lot of good examples in this post, but I wear socks with those black booties that I paired with the purple tunic and grey jeans. I would wear black socks with that. I have these: https://shopstyle.it/l/Xe9w

  6. Jo Lynne, I have purchased 3 pairs of boyfriend jeans. They are rather baggy and loose but they are very comfortable. I wear the with a belt and tucked in T shirt. Should I cuff the jeans and just show off my booties? 

  7. I always love seeing different ways to wear ankle boots like this, Jo-Lynne. I think my favorite way lately is with dresses because it seems modern. My mom always complains about the cutting off the leg line. But I almost wonder if that isn’t an outdated thought (you know like no white after Labor Day?) I mean, I get the idea of looking leaner, but when people meet me in real life, I’m not going to pull the wool over anyone’s eyes about being short!!!
    XOXO
    Jodie
    http://www.jtouchofstyle.com

    1. I had to get used to the look. I used to think it looked so clunky and stupid. LOL! I mean, I really hated it. Somehow, I’ve come around. I think it has to be done right, though. The bootie has to be flattering and slenderizing, the colors of the outfit have to work together to they don’t chop you up too much, and the proportions of the skirt and top have to be adjusted to work with a higher shaft. I guess it’s like anything else in the realm of fashion, you have to figure out how to wear the look so you look balanced and well proportioned.

      1. That’s really a good point, Jo-Lynne!! You have to figure out the proportions, and that’s always been hard for me. But just like everything, the more you analyze it, the easier it becomes (I think and hope…ha ha)
        Maybe that’s why I love my sock booties—they aren’t chunky?? And with the taller boots, I feel like I can wear somewhat shorter skirts yet not feel sleazy!!
        XOOX

  8. Great post! The use of photos really helped me as sometimes I struggle with how much “skin” to show. I have pinned this post so I easily can revisit it. Enjoy your last pool days.

  9. Great tips! I especially love wearing my black suede booties with black tights and skirts or even pretty formal dresses. I love the edginess of a formal-ish dress with booties!

  10. This post is great. The only question I have is what kind of socks do you wear w ankle boots? No show? Ankle socks?  I can’t see any sock in your boots so I was curious. Plus this is always an issue for me 😊

    1. I don’t usually wear socks in the fall, but I have these that I wear with Converse, and they would work under the ankle boots with the lower shafts: http://shopstyle.it/l/TMgJ

      When it gets cold, sometimes skip the ankle boots in favor of knee-high or over the knee boots, or I wear trouser socks with the taller ankle boots, when my jeans cover them.

  11. This was very helpful.  Sometimes I buy all the right things, but then when I try to wear them, they don’t look right.  Posts like this help us pull it all together.  Thanks!!

  12. This is such a helpful post! I love seeing the booties with all the types of jeans I bought at the #nsale and how they are styled with skirts and dresses too. I am excited for bootie weather but not what comes after fall. 

  13. I have a fine arts background, as well as working in merchandising and ‘window dressing’ on my CV. I have to say, that when I see a woman wearing ankle boots with ultra short pant length (i.e. the bottom of the pant leg falls about three inches short of the top of the ankle boot) I think they look horrendous!

    It’s right up there with looking like Elly May Clampett or Forest Gump’s twin sister.

  14. I love your post,,,but my problem is with back problems I cannot wear to many heels,,,,,,any ideas ho ar boots that are flat,,,,thanks in advance,,,

  15. Hello!  Just discovered your blog and am loving your tips!  I’ve been looking for a new pair of booties and love the ones you paired with the white skinnies!  Can I ask what brand/style they are? Thank you! 

  16. Having grown up with ‘highwaters’ in elementary school into middle school, I am not comfortable wearing short jeans even over 50. Capri pants are even out of the question. This year I will give it my best shot. Even though this particular blog is about short boots, are high boots with jeans tucked into them still in style? I have some delicious boots.

    1. Haha, my husband says the same thing about wearing high waters in elementary school. 🙂 Yes, high boots over jeans is definitely still in style! I think that look is so much easier to wear and generally more flattering. To say nothing of warmer! 🙂

  17. Found this post via Pinterest and love it! I have long legs but a short torso and have struggled all my life with pants that are too short, feeling just not right in skinny jeans and boots. But after reading this and the detailed descriptions of why certain combos make sense I feel like I know what to look for when I shop next time! And I found some tall jeans in some of your links so I’ll try them out. Thanks so much for your blog!!  I’ll be back often!

  18. In East Texas and it is starting to get cool so I’m struggling with jeans and shoes again. I only do heels on Sunday so what about comfy shoes that are warm with skinny jeans? I think most of the trends/styles right now are rather tacky so this is very hard for me.

  19. Thought you’d like to know, I was trying my boots with a new pair of skinny jeans and wondering if they looked ok.  Then I thought – I’ll search that Jolynne ankle boot post!  Thank you for your help in keeping me on trend!!!

  20. Great suggestions and cute ideas, but all the short shown have 3-4 inch heals. Not all short boots have heals. I personally have 2 pairs of flat short boots.

  21. Hello, Jo-Lynne…  You’ve put so much work into this blog – I was blown away by how much thought went into each shot, and the explanations helped as well.  I love ankle boots, but I’ve gotten the look so wrong at times, and ended up with a frumpy look (not quite what I was going for).  I’m 5’10”, quite slim still (at 60), but have found that even at my height, a little bit of heel makes all the difference.  So glad to see you mention that here – I’ve eliminated some boots from my wish list on shopping sites based on that.  So many things to remember – not too high, not too flat, up to date heel shapes (I love block heels).  I have thin ankles, so not too baggy around the tops…  I’ve been looking at a couple of shoe sites here in Australia for months now, deliberating, but feeling more overwhelmed by the minute, so I did a search for how to wear ankle boots, and found your blog.  I can’t thank you enough…

  22. Thank You, Thank You, Thank You!  Now that I have a pair of snakeskin booties, I have been wondering how to style them with my jeans.  Wearing the right tops is definitely something that I will have to work on.  Like your oldest daughter, I had to work really hard in school to make good grades.  I was one of those that had a live/hate relationship with school.  Oh, how I wish our temp had been in the upper 50’s this morning instead of the 70’s.  Have a great day!

  23. Love the guidance on the ankle boots!  I have a pair of green suede ankle boots and also a pair of rust colored ones (love my fall colors) which I have owned for a while but haven’t worn yet.  Do you have any advice on wearing different colors of boots so I don’t look cut off?  Thanks!

  24. My favorite look is with skinny jeans but I do love the black skirt, tights, and ankle boots look as well. That picture from Pinterest is Merrick White from Merrick’s Art. Love her style too! 

  25. Thank you for this post! I was googling around looking for help about pairing boots/booties with pants. I have very short legs for my height and I am carrying more weight these days and have little fashion sense on my own! This was helpful.

  26. I just bought 2 pairs of ankle boots today and I just found your blog and I love that I have found you just in time!! The best part is you are my exact age and you have fantastic fashion tips that I’ve desperately been looking for!!! I’m your newest biggest fan! Thank you!

  27. Love your blog and the wide range of idea on how different options look. some ‘experts’ show only one style and say that every other method is wrong. In your selection I can find my favorite way to wear jeans and heels My favourite being 4″ high chelsea ankle boots combined with skinny jeans or boot cut jeans

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