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 Falasha October 26, 2017 at 2:33 pm

    I love every way but my recent favorite is cropped. I have to tell my self to stop cutting the bottom of my jeans because I love this look so much. I think it draws more attention to the shoes.

    xoxo Falasha
    Bite My Fashion
    Instagram| Bloglovin’| Facebook

  • Reply Elise Ward Joyce October 26, 2017 at 2:23 pm

    These are fabulous dos and don’ts! Love that pink sweater too!

    xx, Elise

  • Reply Liz H. October 26, 2017 at 12:54 pm

    Boots are my absolute favorite thing about fall! I just love all of your examples. You styled all of these perfectly!


  • Reply districtofchic October 26, 2017 at 12:33 pm

    I love all of these outfit ideas! Especially cute with the gray boots and cuffed jeans!

    District of Chic

  • Reply Heidi D. October 26, 2017 at 12:05 pm

    These are awesome tips girl! I hate it when It gets so cold that my ankles freeze with ankle boots in the winter, I guess I sort of forgot I could tuck in to some of my jeans!

    Heidi || Wishes & Reality

  • Reply Hey Lena! October 26, 2017 at 11:46 am

    Thanks for the tips! And I love a good pair of black ankle boots!


  • Reply Britney Crawley October 26, 2017 at 11:03 am

    These are great tips, Amy Ann! I love ankle boots for both fall and winter, and it’s fun to see all these different looks.

  • Reply Whitney October 26, 2017 at 10:22 am

    So many cute fall looks! We are big booties fans and love that there are so many way to wear them. I usually have to cuff mine because I am so short and my jeans are always too long!

    Whitney & Blaire
    Peaches In A Pod

  • Reply Ashley White October 26, 2017 at 10:07 am

    Yes! Only tuck when you can keep that calf-to-ankle line slim! Great styling tips, babe!

    Le Stylo Rouge

  • Reply Jacquard Flower October 26, 2017 at 9:11 am

    Such a great post!! These tips are amazing! Have a great day. Gemma x

  • Reply Jodie Filogomo October 26, 2017 at 7:51 am

    This is fabulous Amy!!!
    I’m mostly a cuffer (because I’m so short), but I may have to try the tuck….

  • Reply Gina Daily October 26, 2017 at 7:50 am

    This is such a great post! I pretty much follow these instinctively but it’s so helpful to see the visual and each of the explanations.
    Gina || On the Daily Express

  • Reply Lauren {By Lauren M} October 26, 2017 at 6:51 am

    These tips are so fab! I never tuck my jeans into my booties, but I’ll have to try it!
    By Lauren M

  • Reply Jaymie Ashcraft October 26, 2017 at 5:40 am

    Great guide!!

  • Reply Rachelle October 26, 2017 at 5:24 am

    This is so helpful, so happy booties season is here.


  • Reply Susan Jeffries October 26, 2017 at 5:12 am

    This was so helpful! I have never tucked or cuffed my denim, but these are such great tips!!

    • Reply Amy Ann Arnold October 29, 2017 at 2:34 pm

      So glad you found it helpful! Thanks for commenting and letting me know. 🙂

  • Reply Mes Voyages à Paris October 26, 2017 at 5:12 am

    You look fabulous! love the look with white boots!!!
    Mónica Sors

  • Reply The Fashion Folks October 26, 2017 at 4:14 am

    Love to tuck in the jeans, a chic and nice detail! Xx

  • Reply Merel van Poorten October 26, 2017 at 3:35 am

    Such a great guide! Thanks for sharing babe <3

    X Merel

  • Reply Natali October 26, 2017 at 2:12 am

    Loved the idea of this post! Well done! 🙂

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