Breaking Down How to Wear Boots with Jeans

Some of the most common questions I get are during the fall…

“What boots do I wear with these jeans!? Can I wear these boots with those jeans? Do I cuff my jeans or tuck them in?”

To add to the chaos, you have like a zillion different types of jeans: boyfriend, girlfriend, skinny, cropped, ankle, mom, etc. And, a zillion kinds of boots… all with varying shaft heights.

It is VERY confusing! So… I’m walking you through how to wear ankle boots, with each specific kind of jeans… so you don’t have to wonder or worry anymore. Plus, I’m sharing my go-to way to wear skinny jeans and booties…

how to wear ankle boots with jeans, fashion blogger guide for cuffed skinny jeans with booties, Frame skinny jeans, Louise et Cie black booties, black Theory faux leather blazer

Why It’s So Hard to Decide How To Wear Boots & Jeans

I’m breaking down how to wear ankle boots with different jean styles. Specifically, I’m sharing different leg silhouettes. As I mentioned above there are SO many types of jeans, but you only need to worry about the shape of the leg when figuring out what boots to pair with you jeans. There are four main shapes: 1) Skinny 2) Straight 3) Wide-Leg and 4) Cropped.

I’ve got every shape covered in this post! Yay!

More Questions?

If you still have questions after reading this post, I’ve done TWO videos on how to wear boots with jeans so make sure you watch those here and here.

And… you can also visit us in the Hive for positive and encouraging feedback from my team, and like-minded women!

Erin Busbee of Busbee Style- Fashion over 40 illustrates how to wear boot and booties with different styles of denim including skinny jeans, straight or tapered jeans, wide leg jeans, and Cropped.

#1 | Skinny Jeans

With skinny jeans and boots, the key is to minimize bunching. Your jeans shouldn’t compete with your boots. With the traditional skinny jeans, you have multiple options. (I did a video on how to wear ankle boots with skinny jeans if you want to go back and watch it here.)

With skinny jeans, you have 4 main options (pictured above):

1) Tuck In: Tucking your skinny jeans into your boots works especially well with knee high or over the knee boots.  You can also tuck them into booties, but be sure to pick a pair that have a bit of width in the shaft so that they don’t bulge.  Black jeans tucked into black booties creates such a long lean look and is perfect for those that are looking to appear a bit taller.

2) Small Cuff: This is exactly what it sounds like.  Roll up the hem of your jean into a small (approximately 1″) cuff exposing just a sliver of skin between the top of the boot and the bottom of the jean.

3) Large Cuff: The large cuff is fresh and modern.  Just cuff the bottom of your jean one time into a larger (approximately 2″) cuff.  As with the small cuff, leave a sliver of your skin exposed.

4) Double Cuff: You can use this cuff when you have a bootie with a higher shaft.  Fold your jeans up into a 1″ cuff and then fold them over again.  This looks neat and clean and is ideal for hiding any ankle details (like a frayed hem) that you may not want to show.

BONUS TIP – Tuck under: Another option is to tuck the jeans under so you can’t see the contrasting color on the inside of your jeans.  You may want to do this if you are looking for a cleaner leaner look.

I show you how to do all of these in this video.

#2 | Straight & Tapered Jeans

Straight leg and tapered jeans have roomier legs and either…you guessed it, go straight down or taper toward the ankle. With either style, you can do a small cuff, large cuff, double cuff, or a tapered cuff (pinch one side of the bottom of the jean and roll it up one or two times). Again, make sure you watch the video to see exactly how I do these if you’re unsure!

#3 | Wide Leg Jeans

Wide-leg jeans are pretty dummy-proof. Since they’re SO wide at the bottom…you do nothing!

#4 | Cropped Jeans

The next pair of jeans I want to tackle… is the cropped jean. Ankle boots and cropped jeans are a match made in heaven. The hemline of the jean is typically not going to compete with the boots, which means you do NOTHING. Yay!

More Quick Tips for Booties & Jeans

  • Tucking your jeans into your booties should be reserved for skinny jeans.  They tend to look best when the tones are similar.  For example, tucking black jeans into black booties or dark blue jeans into dark booties tends to look best.
  • Look for  booties with a fitted shaft (especially sock booties) to wear under your jeans. This style of booties is perfect to wear under straight, tapered, and wide-leg jeans.
  • If your booties aren’t fitted to the calf and they are taller, more like mid-calf booties, try cuffing your cropped jeans. (works best on skinny and straight-leg jeans)
  • Over the knee and knee-high boots always go over skinny jeans.
  • Combat style boots look best paired with tucked in skinny jeans



Boots With Jeans, Erin Busbee of Busbee Style sharing the complete guide to wearing jeans and booties wearing Frame skinny jeans, Louise et Cie black booties, a black Theory faux leather blazer, and white BP lace cami in her home in Telluride, Colorado, how to wear boots with jeans

My Go-To Cuff

One large cuff is one of my go-to’s for when I wear skinny jeans and booties. I’m petite so most jeans are longer on me unless I get them in an ankle or cropped length. These jeans by Frame are not cropped so I’m able to do more with them. I did one large cuff and I love how they look with these cute black booties. These are the exact jeans and booties I’m wearing in the graphic above. So you can see how they look tucked in, a small cuff, and double cuffed. All of them work but I love the large cuff for this look!

Do you have any other questions about how to wear jeans with boots? What’s your favorite way to wear jeans and booties? Please share in the comments!

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Thank you for stopping by!

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