How to Wear Ankle Boots With Straight Leg Jeans

December 18, 2019

My blog post about how to wear ankle boots with jeans is my most popular blog post to date with my what shoes to wear with cropped jeans being a close second. I have received a few questions about how to wear ankle boots with straight leg jeans, so today I am here to deliver!

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To be honest, this is a style I have always envied others wearing with ease. Wearing ankle boots with straight leg jeans didn’t come as naturally to me as skinny jeans. SO I began researching and trying things out in hopes that I could put together a comprehensive and helpful post for you all. Below is what I have learned to be the most important things.

First Pick the Right Straight Leg Jeans – The Cut and Length of Your Jeans Matter

I have some straight leg jeans/relaxed “mom” style/boyfriend jeans, and I have just never liked the way they looked with my ankle boots. This started a quest to find the right jeans. Enter three pairs of jeans that fit the bill and have since been on constant rotation. Here’s what made the difference:

  1. You want a pair of straight leg jeans that are on the slim/straight side, i.e. look for a more narrow cut as opposed to a wider, looser cut of straight leg jeans.
  2. Length matters! You do not want a capri jean here. Find a jean that hits just above your anklebone. I discovered this was really my main issue. I am tall, and all the straight leg jeans I owned were short due to my height. They were not cutting it.

Straight Leg Jeans I’m Wearing in This Post

As I mentioned above, finding the right length for YOU is key. At 5’10”, I normally wear a 30 in inseam in a full length skinny jean. I sound what worked best for me as a straight leg jean with boots was something in the 28.5-29.5 range. For me, this meant paying some as it was harder to find. I am wearing the Paige Sarah Slim jeans (28.5 in inseam), the GRLFRND Karolina high rise “skinny” (called that even though it is more of a straight cut 29.5 in inseam though it has other shorter versions), and the Madewell Stovepipe in a tall (29.5 in inseam).

If you are looking and are shorter than I am, I would recommend Levi’s 501 “skinny”, Levi’s in general, or Madewell’s straight denim in regular or short inseam lengths. I do prefer one that is not all cotton just for comfort.

How to Wear Ankle Boots with Straight Leg Jeans

Example One – Let Your Jeans and Your Boots Almost Meet

Of all the ways to wear ankle boots with straight leg jeans, letting your jeans and your ankle boots almost meet is probably the easiest option. In the first set of photos below my jeans are the Paige Sarah Slim jeans (28.5 in inseam). The boots I am wearing have a taller shaft on them as opposed to a true shorter ankle boot. The combination is perfect to let them just almost touch. In the second set, my jeans are the Madewell Stovepipe in a tall (29.5 in inseam). My boots are slightly shorter, but they still meet perfectly.

DO pick a boot height so that the top of your boots just almost touch the bottom of your jeans.

DO NOT pick a boot that is too low and shows too much skin or too high and causes your jeans to bunch.

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Example Two – Cuff Your Jeans

In this example I am wearing the GRLFRND Karolina high rise “skinny” which have a 29.5 inch inseam. Since they are a bit longer, I needed to cuff them slightly. This works since they are a slimmer straight leg jean which is key as I mentioned in the first section.

DO cuff your jeans when they would otherwise bunch over your boot.

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Example Three – Try a Sock Boot

I love a sock boot to pair with a straight leg jeans! A “sock boot” is a boot that has a boot shaft/top like a sock and is very fitted to your ankle and calf. They typically go up a little higher on your leg as well. They are ideal to pair with a straight leg jean because they slip under your jeans perfectly! I’m wearing my same Paige Sarah Slim pictured in the first set.

DO slip your sock boot under your straight leg jean.

DO make sure your jeans are long enough to cover the top of your sock boot.

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Boot Tips

In general there are a couple of things I would avoid when considering how to wear ankle boots with straight leg jeans well. The main one I already mentioned in the jeans section and that is to avoid wearing a super wide leg/boyfriend style jean. I have and love these style jeans, but I tend to wear them with a more sleek mule or side as opposed to a boot.

The other main tip I have for you is to try a boot that comes up a but higher and narrower on your ankle as opposed to a true short ankle boot. Notice how all of mine have a higher boot shaft and are narrow. This helps them look a little more streamlined and flattering with the straight leg.

Style on the Daily with On the Daily Express

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20 Comments

  • Reply Jessica December 25, 2019 at 3:39 pm

    I love all these dear, especially the last two looks!

    Jessica | notjessfashion.com

  • Reply Laura Bambrick December 19, 2019 at 3:02 pm

    These are such great tips and the denim you found looks fantastic on you with ankle boots!

  • Reply regina smith December 19, 2019 at 1:50 pm

    Thank you for the helpful tips. I am 6’with a 34” Inseam. Like you, jeans are difficult to find in the right length.

  • Reply Julia December 19, 2019 at 1:05 pm

    Thanks for these great tips! I love wearing ankle boots but sometimes have problems with the length of the jeans as they bunch over! I hadn’t even thought of cuffing them! I love those sock boots too!
    Julia x
    https://www.thevelvetrunway.com/

  • Reply Jacqui Berry December 19, 2019 at 11:05 am

    Lovely way to wear them, I need to find the right length for me! Thanks for sharing and hosting. Jacqui

  • Reply Vanessa December 19, 2019 at 10:17 am

    Such great tips, Amy! I love ankle boots! They are so chic!
    xoxo, Vanessa
    http://www.WhatWouldVWear.com

  • Reply Gemma December 19, 2019 at 8:27 am

    Loving every single look! Amazing inspiration as always! Happy Holidays to you and your family.
    Gemma x
    http://www.jacquardflower.uk

  • Reply Cheryl Shops December 18, 2019 at 11:45 pm

    As someone who loves both straight-leg jeans and ankle boots, I found this super helpful! Agreed on finding the perfect inseam, and I think it helps to look for a boot with a lower shaft too (i.e. one that hits at the ankle bone).
    Cheryl Shops | http://www.cherylshops.net

  • Reply Maureen December 18, 2019 at 2:51 pm

    You definitely make it look easy Amy! I love how effortless each of these styles look and I agree that the length of your jeans make a difference.

    Maureen | http://www.littlemisscasual.com

  • Reply Noelle Engel/ Beautygirl24 December 18, 2019 at 2:44 pm

    Love these tips! Definitely bookmarking this for future reference! I’m wearing my new booties with my fave jeans on my blog today and I think I followed your guidelines 😉

  • Reply Lizzie December 18, 2019 at 11:06 am

    These are such great tips! I usually have issues trying to style this since I’m so petite but you’ve inspired me to try it out again 🙂

    Lizzie
    http://www.lizzieinlace.com

  • Reply jess jannenga December 18, 2019 at 9:47 am

    Amy, I pinned this, as I LOVE this look! I have mainly skinny jeans, a pair of boyfriend and cropped culottes styles. I am not sure I have a straight style.! We both are tall and wear the same inseam with skinny jeans, so it was interesting when you posted about a 28.5 -or so, as I think it would needaltered unless I find a pair in that length. Very helpful and you look great!
    Merry Christmas to you and your family!
    jess xx
    http://www.elegantlydressedandstylish.com

  • Reply Ellibelle December 18, 2019 at 8:32 am

    Such great tips and loving all these looks!
    Thanks for sharing!
    Ellibelle’s Corner

  • Reply Kelly R December 18, 2019 at 8:00 am

    I love the look of straight leg jeans! I feel like they are the perfect pairing with cute booties! Happy Wednesday girly!

    Rosy Outlook

  • Reply Amy Johnson December 18, 2019 at 6:55 am

    These are such great tips! You are so good at posts like these. Love your outfits too.

  • Reply Jill December 18, 2019 at 6:25 am

    These are great tips! I agree, the length of your jeans is key! All of these outfits are so cute! Love those sock booties!

    Jill – Doused in Pink

  • Reply Shelbee on the Edge December 18, 2019 at 6:18 am

    These are really great tips for styling booties with straight leg jeans. It is funny how in tune I have become to styling pieces in the ways that look best and I notice bunched up jeans not quite right with boots on passers by and I want to stop them and give them styling tips! But of course, you can’t do that unsolicited! Ha. People are easily offended.

    Shelbee
    http://www.shelbeeontheedge.com

  • Reply Meagan Brandon December 18, 2019 at 6:08 am

    Great post! I love your black tunic sweater with those classic ankle boots – so chic!

    Meagan
    http://www.meagansmoda.com

  • Reply Andrea Nine December 18, 2019 at 6:06 am

    YOU wear ankle boots so sweetly!!!

  • Reply Madeline December 18, 2019 at 4:41 am

    Love wearing ankle boots with straight leg jeans, so I love these ideas on how to style them together. Swooning over all these ankle boots now 🙂
    CappuccinoAndFashion.com

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