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 May 6, 2019 at 8:49 am

    Hola! I’ve been reading your web site for some time now and finally got the bravery to go
    ahead and give you a shout out from Lubbock Tx! Just wanted to mention keep up
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  • Reply Brigette fahey March 14, 2019 at 8:47 pm

    Thank you for the advice! I have just finally bought two pairs of ankle boots in hopes of not looking rediculous in them but haven’t had the courage to wear them yet.
    Now that you have cleared up how to dress them properly I’m going to finally go for it.
    I do have a question about how to dress with the pair that are a slip on wedge that come just above my ankles. They are a black with a rose gold metallic tint. They look a bit “Herman Munster’esqu” but are adorable. If you have any ideas I would appreciate your help.
    BTW, you were gorgeous pregnant so don’t apologize. I’m sure the pregnant gals appreciate knowing that they can look stylish too.

  • Reply Ocsurfgirl February 9, 2019 at 11:27 pm

    Great tips! Love your outfits, especially the blue striped poncho.

    Can you tell me where it’s from?

    Thank you!

  • Reply SBecky February 5, 2019 at 12:57 am

    Great tips for skinny jeans, but they don’t look great on all body types, i.e pear shape. Do you have any tips for streaight leg or boot cut jeans?

    • Reply s moran March 8, 2019 at 9:15 am

      Same question, I don’t wear skinny jeans and wear a lot of skirts and dresses so cal life. Lets see ideas for Non skinny jean styles?

      • Reply Amy Ann March 12, 2019 at 7:03 am

        Thank you both for this feedback! I am sending you each an email response so it is sure to be seen. I am also keeping this in mind for next season to do as a post. Please comment with any specific questions/feedback about things you would like covered in a post. I appreciate you reading and taking the time to comment! I have posts styling boots with skirts/dresses and also straight leg jeans with boots, but not one round up like this with tips broken down. You can use the search function or also the fashion tab at the top of my menu bar to look through. I hope that helps some!

  • Reply Gretchen February 4, 2019 at 5:32 pm

    So jealous of your wardrobe! Great suggestions…love them all! Lmk when you are cleaning out your closet?

  • Reply Jess January 26, 2019 at 9:39 pm

    Love how chic you make everything look. I especially love the pink top look. Great examples. Love this!

    • Reply Amy Ann January 29, 2019 at 12:15 pm

      Thank you so much! I am so glad you found it helpful!

  • Reply Dayle Harding January 23, 2019 at 11:52 am

    I have a pair of tight stretch denim jeans that Aare too short. They have a thin gold piping on the leg. There is too much leg space so I guess higher ankle boots. Right now I have knee high boots. Will that work

    • Reply Amy Ann January 23, 2019 at 12:50 pm

      Hi! Yes, if you are wanting to wear them with an ankle boot, I would recommend a taller ankle boot (one that goes above your ankle bone). A knee high boot or even an over the knee boot would also work. I just wrote a post about how to wear over the knee boots here if you are interested

      • Reply Cami March 8, 2019 at 9:58 am

        The tight jeans with the gold strip around the high ankle is good for the bootie, depends on her style.. she should shop for the right look. the knee boots are a old style now.

  • Reply Sophie Lee December 2, 2017 at 9:19 am

    Wow these tips are so useful, i’m into ankle boots these days and this post is the best thing i need <3

    xxoo, Cool style for men

  • Reply Laura Boswell November 7, 2017 at 6:06 am

    Really great post! I love all the tips especially with the certain ankle jeans and the booties.

  • Reply Virginia Evans October 30, 2017 at 3:58 pm

    Great post Amy Ann! So many good example photos! So useful!

    More to Mrs. E

  • Reply ADA October 30, 2017 at 1:24 pm

    WOW what a great and thorough post. I am definitely bookmarking this one. You went through all the options. I am all about booties for Fall and Winter. I love them best with jeans. Loved your collection of booties and you were so cute pregnant.

  • Reply fashionistha October 28, 2017 at 3:12 am

    Love those pencil heels one. Too trendy!

  • Reply Jessica October 27, 2017 at 11:52 pm

    Ankle boots and jeans combo is just one of the many reasons why I love fall.

    Jessica |

  • Reply Kristin Kohler October 27, 2017 at 11:11 am

    Cuffed is my favorite! Even when I have jeans that don’t need a big cuff, I almost always just roll the hem up slightly. The better to showcase the booties 🙂

  • Reply Gentry October 26, 2017 at 9:38 pm

    A cuffed jean with booties is my FAVORITE fall look! In fact, I just wore it today! What a fun post idea!

  • Reply Laura October 26, 2017 at 9:21 pm

    My bootie collection just keeps growing! There are so many great ways to pair them with pants! Love your tips!

  • Reply Luci's Morsels October 26, 2017 at 8:49 pm

    Ankle boots create some of my favorite fall looks! Love the options you give here for styling the boots, such a variety of ways to wear this great trend!

    Luci’s Morsels | fashion. food. frivolity.

  • Reply Mercy October 26, 2017 at 8:43 pm

    So creative of you to come up with this post, it is very helpful and yes detailed is good.

  • Reply Jacqueline Rendine October 26, 2017 at 8:24 pm

    These are all great ways! I started to cuff mine this year!
    Stylin In St. Louis

  • Reply Jessi Malay October 26, 2017 at 3:38 pm

    I’m all about ankle boots with denim, especially for fall!! Love how you styled all these babe <3

    XO, Jessi

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