How to Wear Ankle Boots with Jeans – The Dos & Don’ts

October 26, 2017

Ankle boots are my JAM. Seriously, fall is my favorite because of B-O-O-T-S! Sometimes wearing boots can be tricky. I have different pairs of denim I wear different ways with different pairs of boots, and today I am breaking it alllll down for you guys. Seriously, this might be a little too detailed but let me know if you have any questions.

Hi! New here?? I’m so glad! This post is getting lots of traffic from Pinterest, so I thought I would take a second to introduce myself. I’m Amy Ann, mom and wife, and I love sharing my everyday life and fashion here. I’d love for you to follow along on Instagram, Facebook, or Pinterest. You can also find similar posts to this one about how to wear ankle boots with straight leg jeans, when to tuck and not tuck your shirt and what shoes to wear with cropped jeans. Now back to boots. 🙂

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How to Wear Ankle Boots with Jeans – The Dos & Don’ts

Cropped Denim

This is perhaps the easiest way because your jeans do all the work for you. If you are wearing a cropped pair of jeans, they are already not going to conflict with your booties.

  • Do let your denim hit above your booties
  • Don’t let there be too much skin between the bottom of your jeans and the top of your booties. This may mean (depending on how cropped your jeans are) that you need a taller ankle bootie (one that hits above your ankle bone) as opposed to a shorter pair. In both pictures below, I am wearing one of my taller booties.


Tuck Your Jeans In Your Boots

This one is the trickiest of all in my opinion.

  • Do tuck your denim when it is very skinny at the ankle and will not bunch. It also has to be long enough to tuck.
  • Do tuck your denim when your boots have a wider opening at the top.
  • Don’t try to tuck your denim when your boots are very short (i.e. hit at your ankle), only when they are a bit taller.


Cuff Your Denim

Jeans that are 1.) too long to naturally hit above your booties 2.) not super skinny at the ankle and/or 3.) may be paired with taller booties are great candidates to be cuffed. My jeans below are a great example because they are a thick denim that is pretty long and not super skinny at the bottom. Any bootie I pair them with really means they need to be cuffed because it causes them to bunch.

Do cuff your jeans when they would otherwise bunch over your booties.


Do Nothing

Sometimes your jeans are just regular length skinny jeans and your boots are ankle length, and there is no need to cuff or tuck. Win!

  • Do nothing when your jeans are skinny/narrow at the bottom and hit just above your ankle.
  • Do nothing when your booties hit at your ankle.

Examples (sorry for a throwback pregnancy one, best I had! Miss those jeans…)

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Ankle Boots I’m Loving

Jeans I’m Loving UNDER $80

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  • Reply MiMi Fuller April 27, 2024 at 9:21 pm

    I have like super long legs, like i am 5’2 and like i basically have no abdomen. I look great in skinny jeans and leggings, but it’s what to wear with them bc i also have bigger boobies. I literally feel like an ostrich. How do i style without looking like a mushroom. I’m 119lbs

  • Reply Amy Wade February 5, 2024 at 7:56 am

    I love all your tips! You always look so put together!

  • Reply Jen January 14, 2024 at 2:05 pm

    I feel like boot cut jeans are really hard with ankle boots; do you have any suggestions?

  • Reply Beth October 24, 2023 at 9:13 am

    Hello! I love your post on how to wear ankle boots with jeans! My question is, are tall boots out? You know the kind, where leggings or skinny jeans are inside the tall boot that comes just below your knee? Thank you!

    • Reply Amy Ann October 24, 2023 at 10:58 am

      Hi Beth!

      I am still wearing a cowboy style tall boot with my leggings as seen in this Instagram reel ( or a shorter chelsea style boot. The more traditional style of tall riding boot seen in this reel ( isn’t being worn as much now. If you don’t follow Two Scoops of Style, they do some really fun reels about how to update your look! I hope that is helpful. Email or comment any time!!


  • Reply Jan Koprivnik October 5, 2023 at 9:23 am

    I thought skinny jeans were out?

    • Reply Diane Walborn November 12, 2023 at 3:06 pm

      Me too! But I’m still seeing them being sold and worn.

  • Reply Jess September 9, 2023 at 8:13 pm

    I’m seventy and I love your look. I intend to wear my leggings and one of my multiple pair of ankle boots whether they’re the last word in fashion or not.
    I’m 5’4” and hundred and sixteen pounds and my legs are my best feature.
    I also notice you shop in places I can afford on a fixed income.

    If people don’t care for your style, there are plenty of other websites that feature other styles. Vive la difference. We shouldn’t all dress they same. We all have strong points and weak points. Legs are my strong point and I feel confident in skinny pants. Wide leg pants make me look like a short, dumpy clown which isn’t what I aspire too. Others look great in them. All of us wearing the same type and style of clothing is called wearing a uniform; I did that for years as a nurse!

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