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.

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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…)

I hope this is helpful! If there is any similar type topic you would like me to post about, let me know.

Ankle Boots I’m Loving

Jeans I’m Loving

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

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

    More to Mrs. E

  • ADA

    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.

  • fashionistha

    Love those pencil heels one. Too trendy!

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

    Jessica |

  • 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 🙂

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

  • Laura

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

  • 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.

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

  • Jacqueline Rendine

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

  • Jessi Malay

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

    XO, Jessi