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.

Examples

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.

Example

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.

Examples

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

Marc Fisher Boots – Use Code LTD2107 for 20% off!!!

Jeans I’m Loving UNDER $80

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66 Comments

  • Reply Rebecca McCray November 24, 2021 at 8:01 pm

    My Sister is a plus size gal, she bought her some black ankle booties. She wears them with her jeans , she cuffs them up at ankle and she looks pretty cute.

  • Reply Dawn Harrison November 5, 2021 at 10:49 pm

    Do not be sorry for the pregnancy pic! Gosh! Pregnant women want to know these tips too!

  • Reply Violeta bagia March 12, 2021 at 5:35 pm

    I love the pregnancy ones! I’m currently 16 weeks with my first and struggling to stay stylish haha! This helped heaps. Thanks!

  • Reply Felica February 3, 2021 at 2:20 pm

    I will be glad when this fad passes…..nothing like taking your legs and cutting them off at your ankle….what happened to the days of long and lean looks. This is one fad I pass on…don’t like the look and you need to be 5’10” with long skinny legs to pull this one off……

  • Reply Kim Zabiegalski February 14, 2020 at 2:17 pm

    Love these tips! Would love a tip on how to ‘roll’ a cuff … as in a a slouchy cuff. I’m a petite women and often have to cuff a few times but love for the unfinished hem to still show. Any ‘cool’ way to do? Thanks!

  • Reply Liz Tylki February 1, 2020 at 7:35 am

    your so adorable with your little baby bump! Great tips..

  • Reply Liz Tylki February 1, 2020 at 7:35 am

    your so adorable with your little baby bump! Great tips..

  • Reply Phyliss Wilkinson November 27, 2019 at 7:59 am

    hello, does anyone else think that ripped up jeans with your knees sticking out is the DUMBEST TREND that has come along in many years???!!??! Why do we do this???…It looks ridiculous! I love the boots & jeans tips…& just signed up to follow you, thanks!

    • Reply Amy Ann Arnold November 27, 2019 at 8:02 am

      Thanks so much for following along and for leaving a comment. So glad you found this post helpful. Sorry yo udon’t like the trend of the ripped jeans. I totally understand that. I personally like it, but I know it is not for everyone. Happy Thanksgiving!

      • Reply Hoda October 1, 2020 at 7:10 am

        Don’t apologise for your pregnancy! Own it 💪

    • Reply michelle diaz January 19, 2020 at 2:42 am

      I agree! But I have a better one to make you crazy — jeans hanging halfway down the butt!! What were they THINKING? Love these boot styles – am going to repurpose a few now!

  • Reply Angela Jackson November 25, 2019 at 6:00 pm

    What advice do you have for knock needed women? What kind of jeans should we wear?

    • Reply Amy Ann Arnold November 27, 2019 at 8:04 am

      Hi! Thanks so much for stopping by and leaving a comment. I just sent you an email.

    • Reply Lo July 13, 2020 at 5:42 pm

      What’s knock needed?? Never heard of that!

      • Reply Dawn Harrison November 5, 2021 at 10:52 pm

        When legs are shaped in a way that the knees touch together, and lower legs are out further than knees
        I see this post is over a year ago! You probably know what it means by now!

  • Reply Do these rules also apply for plus size girls? September 10, 2019 at 7:32 pm

    Do these rules also apply to plus size girls?

    • Reply Amy Ann Arnold November 4, 2019 at 9:01 pm

      I responded over email, but yes! I think they definitely do. 🙂

  • Reply Amanda September 5, 2019 at 9:21 pm

    The black, pointy toe leather booties in your post– where can’t I find those?

  • Reply Paige June 21, 2019 at 7:43 pm

    Great advice on how to wear….
    Thank you

    • Reply Alma July 25, 2019 at 2:20 am

      Great tips I was so worried about cuffing my jeans to hit above the booties. But it does look great

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