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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21 Comments

  • Reply Mona February 18, 2020 at 5:30 am

    I loved your outfit and boots. This is so helpful! Thank you

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