How To Wear Booties With Jeans – Do & Don’ts

Booties With Jeans

Everything You Need To Know About Pairing Boots With Jeans

Many folks ask me questions, especially in the fall, like, “Which boots go with these jeans? Can I pair these boots with those jeans? Should I cuff them?” With so many types of jeans and boots nowadays, it can get pretty confusing! Don’t worry—I’m here to guide you on how to wear ankle boots with jeans, breaking it down for each specific type of jeans, so you won’t have to wonder or stress anymore! Also, I’ll share my favorite way to style skinny jeans with booties…

Why It’s Tricky to Figure Out How to Wear Boots With Jeans

I’ve made TWO videos on how to pair boots with jeans, so make sure to check those out here and here if you still have uncertainties or more questions after reading this post! I’m simplifying how to wear ankle boots with different jean styles.

Yet, to add more complexity, aside from various jean styles and hemlines, there are also different bootie heights and types of booties… Chelsea boots, flat ankle boots, heeled ankle boots, combat ankle boots, and more. Ugh, it can be REALLY confusing!

But, no worries—I’ve got you covered in this post! Yay!

Skinny Jeans and Boots Guide

When pairing skinny jeans with boots, the key is to avoid too much bunching. Your jeans and boots should complement each other. For traditional skinny jeans, you have several options. (I made a video on wearing ankle boots with skinny jeans; you can check it out here.)

Here are the main options for skinny jeans (shown above):

1) Tuck In
2) Small Cuff
3) Large Cuff
4) Double Cuff

Another choice is to tuck the jeans under, hiding the contrasting colors of the denim.

I demonstrate how to do each of these in the video. Some trendsetters are saying skinny jeans are no longer in style, and baggier styles are becoming more popular. However, having a pair of classic dark wash skinny jeans in your closet remains essential.

So, I’m sharing a few of my favorites below in case you’re still looking to check those off your list…

Straight & Tapered Jeans with Boots Guide

Straight-leg and tapered jeans offer more room in the legs, either going straight down or tapering toward the ankle. For both styles, you can choose a small cuff, large cuff, double cuff, or a tapered cuff.

Depending on the pair of straight-leg jeans, you can also leave them untouched, allowing them to go over the ankle boots. Watch the video to see the techniques in action if you’re uncertain!

Options for straight-leg and tapered jeans (as listed above):

1) Small Cuff
2) Large Cuff
3) Double Cuff
4) Tapered Cuff

Straight-leg and tapered-leg jeans are currently a fashionable silhouette, offering a middle ground for those not ready to part with skinny jeans but also looking to avoid baggy styles. Check out a few of my favorite options below…

Wide Leg Jeans with Boots Guide

Wide-leg jeans are incredibly straightforward. Given their ample width at the bottom, there’s no need for any adjustments! This advice also extends to flared or bootcut jeans. Simply leave them as they are and let the jeans gracefully cover your boots.

I absolutely adore wide-leg jeans, and I’ve provided links to some of my favorite options below…

Cropped Jeans and Ankle Boots Pairing Guide

Now, let’s delve into cropped jeans. When it comes to ankle boots and cropped jeans, they’re a perfect pairing. The hemline of the jeans usually won’t clash with the boots, making it simple – you don’t need to make any adjustments.

How convenient! Discover some stylish cropped jeans in the collection below…

Quick Booties & Jeans Styling Tips

Here are some speedy tips for styling booties and jeans:

1) Opt for taller boots over skinny jeans for a sleek look.
2) If your booties are snug around the calf, wear them under your jeans – a great match for straight, tapered, and wide-leg jeans.
3) For mid-calf booties that aren’t fitted to the calf, consider cuffing your cropped jeans (ideal for skinny and straight-leg jeans).
4) Embrace the trend of wearing over-the-knee or knee-high boots over skinny jeans. You can also let them bunch around the knees for a fashionable touch.

My Preferred Style: The Large Cuff

When it comes to wearing skinny jeans with booties, I often go for the one large cuff. Being petite, most jeans are longer on me unless they come in an ankle or cropped length. In this instance, I chose Frame jeans, which aren’t cropped, allowing for more styling options.

I opted for one large cuff, and it pairs perfectly with these chic black booties (similar here as the ones I’m wearing in the graphic above). While tucking in, a small cuff, and double cuff all work, the large cuff is my favorite for this particular look!

Adding a Stylish Layer: Faux Leather Blazer

To complete the ensemble, I matched the jeans with a lace cami and one of my beloved third layers—a faux leather blazer!

If you have any questions about wearing jeans with boots or want to share your favorite style, please do so in the comments! Feel free to share this post using the buttons below—pin it, tweet it, or email it.

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