How to wear booties with jeans | Outfit ideas & the do’s and don’ts!

Last Updated on October 15, 2023 by Eve Dawes

Stuck for how to wear black booties with jeans? 12 outfit ideas for all cuts of jeans & styling tips

How to wear black booties with jeans or any booties with jeans can get tricky or you can easily end up with the same look on repeat. The way that you style them really comes down to the type of booties and the cut and style of jeans you’re planning on wearing. How you wear booties with skinny jeans, tends to be different than wide leg jeans. The same way that combat boots tend to give a very different look to stiletto open toe booties and therefore need styling a bit differently. Black booties are one of those classic style wardrobe essentials but these looks work just as well with other colors and prints. There’s really 2 ways to wear booties with jeans, under or over, but so many ways to style those 2 looks. There’s also some do’s and don’ts to make them work and look their best.

So whether you’re planning on straight, skinny or wide-leg jeans, these are some ways to style your booties and jeans from classic to fashion forward outfit ideas.

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After reading this hopefully you’ll know:

• When to wear booties under or over jeans.
• How to wear booties with all cuts of jeans: wide, bootcut, skinny jeans etc.
• What kinds of jeans go the best with different styles of boots.
• Have lots of jeans with booties outfit ideas.

How to wear booties with jeans style guide

It can be tricky knowing how to style booties with jeans to make them look flattering. Mainly because there’s so many styles of boots and jeans to choose from. Which is why I wanted to give you lots of different outfit ideas and style tips for all kinds including boyfriend jeans, flared jeans or your favorite pair of skinny jeans.

So grab your best boots and give these different options a go to get more wear out of your favorite booties.

How to wear black booties with jeans?

Do black ankle boots go with jeans? Yes, absolutely, black booties with jeans is a classic look. How you wear black booties with jeans all just comes down to choosing the right color and cut of jeans to go with the style of booties for the most flattering look.

Black booties tend to work best with jeans for Fall and Winter rather than in warmer weather or with jean shorts as they can look too heavy.

I tend to go with lighter shades of booties like pink and white for Spring with dresses or shorts.

How do you wear jeans with booties in 2023

Straight leg jeans are a more fashion forward way to wear jeans with booties in 2023 than skinny or flared jeans. High waisted jeans like Agolde 90s straight leg jeans are one of Revolves best sellers. You can still cuff your jeans but it’s a bit outdated for 2023. If you really want to do it, try rolling them for a more casual and effortless look.

Another big trend for 2023 is crop tops. If crop tops aren’t for you, try them under sheer shirts or blazers for a bit more coverage. I’ve been wearing my ankle boots with leather pants more than jeans this season. As they’re warmer and more on trend but am about to get my jeans back into rotation.

Can you wear jeans over booties?

Yes styling jeans over booties tends to work better for most styles of ankle boots but it doesn’t work with all styles of boots. As a general rule, if your booties are short don’t tuck your jeans in as they’ll just keep coming out. If you’re booties are longer e.g almost to your calves, they’ll probably look best tucked into skinny jeans.

Are skinny, straight leg or wide leg jeans better to wear with booties?

The jeans you wear will depend on the boots you’re wearing for the most part. If you’re wearing a pair of booties where the detailing or logo is at the top and you want it to be seen, skinny jeans tucked into the boots, boot slit jeans or even leggings are the way to go.

If you’re looking for a more casual look and don’t care about showing off the top of your boots, wider or bootcut jeans work really well.

Easy & flattering monochromatic booties and jeans outfit

Black jeans look great with black boots for a sleek monochromatic look. This is one of the simplest ways to wear this and look works particularly well if you’re petite like me. Styling black jeans with a pair of black booties doesn’t cut you off at the ankles like mixing 2 colors would. Instead it creates a longer, unbroken silhouette and is one of the most flattering ways to wear black booties with jeans.

A lot of blues don’t look that great with black either. So styling black booties with black denim solves that problem and is probably the easiest and most classic way to style your ankle boots. Which is why it’s probably my favorite way to wear this look. Especially with either straight leg or black skinny jeans to look even more streamlined.

To make this look work the best go for a wash that matches your boots. EG if you have distressed boots, go for distressed black jeans. If you have brand new black booties, a plain black wash is perfect. The idea is to create as seamless a transition between the pants and boots as possible.

How to style black booties with jeans to show off your booties

If you want to show off your booties either roll or cuff your jeans, go for a narrow pair that you can tuck into the boots without creating bulk or look for a boot slit pair like these GRLFRND jeans.

I know I said before it’s not really in to cuff for 2023 but just because something’s not necessarily “in” doesn’t mean it isn’t a classic or can’t be done. Do whatever’s the most flattering on you, more than what’s in style right now.

Another option is to look for a boot split hem that the boots can be seen through. High low hem jeans are another great option for showing off sock boots or boots with detailing like chains, gold hardware or the logo at the top.

Classic Fall black booties with jeans outfit

If you’re wanting to wear booties with jeans on a rainy day a trench coat will always be a classic. It’s a great option for styling this look when it’s damp out. It doesn’t matter whether you do blue or black jeans for this look or go for neutral or a bright color on top. It’s stylish and the elongated top makes for a flattering silhouette.

Classic casual black booties with jeans outfit

Style your jeans and booties with a plain or graphic sweatshirt layered over a button down shirt for a classic and chic look. I like layering as I tend to boil inside if I just go for one thick layer. You can either go completely black with this look, wear a black sweater over a white button down or break up the look with colors on top.

It’s a versatile look that can be worn in a lot of different ways. This outfit combo works really well with pointed toe heeled boots as well as Chelsea boots but it all comes down to personal preference.

Americana Fall favorite

A simple and casual outfit for fall is either heeled, cowboy boots or flat booties with black or blue jeans and a plaid shirt or shacket. Perfect for going for apple cider and to Pumpkin patches. I also like this look with blue or black jeans and brown or white ankle boots. Sandwiching colors like a cream jacket and cream boots really helps to tie the whole outfit together.

Effortless everyday casual booties and jeans outfit

Black or blue jeans styled with a white t-shirt and black booties makes for a great effortless everyday casual outfit. It’s one of those boots and jeans outfits that’s to dress up or down depending on the style of bootie. As well as how you accessorize your outfit. Flat ankle boots or block heels will obviously look more casual than stiletto heels.

Go for a graphic tee or plain white tee depending on your personal style. To elevate this look a little bit, layer a blazer over the top.

Layer up

I’m a fan of layering so that I can always be the right temperature. Pieces like an oversized sweater, scarf, duster cardigan, jean jacket or black leather jacket are all easy to layer with. They also go with pretty much any style of jeans and booties.

How to wear flare or wide leg jeans with booties

Wide leg jeans look great with a bodysuit or contrasting dimensions or styled with a trending top to make this look on trend for 2023. They work with pretty much any pair of boots. My personal preference is a less chunky shoe like a pointed pair of boots so that it’s not too much bulk. It also helps to keep the look more elegant. Just make sure the top of the bootie goes high enough to go completely under the jeans.

This look works just as well with brown booties as black. Trends in the past have included cropped wide leg pants with ankle booties but this is an incredibly difficult look to pull off without it making your legs look super short and disproportionate.

How to wear booties with skinny jeans

I tend to lean towards skinny or straight leg jeans a lot of the time. As this cut goes with booties, knee high and over the knee boots. I also find they make your legs look longer than a lot of other styles. However, there’s a few of trains of thought when it comes to how to wear booties with skinny jeans and both are right, let me explain more.

Some fashion editors and stylists will say to:

1. Style skinny jeans under your booties .
2. Wear your skinny jeans tucked into your booties.
3. Show a hint of ankle with a pair of skinny jeans that hits just above where your ankle boots end.

When it comes to styling skinny jeans with booties it doesn’t really matter if they go under, over or stop above your boot. As long as they don’t bunch over the boots when tucked in, bulk out where the boots are underneath, or cut your legs off to make you look shorter. I’ve worn these black skinny jeans both under and over my black ankle booties.

How to style combat boots and jeans

Because combat boots tend to have an edgier look they look great with more casual laid back styles. Think distressed or ripped denim jeans or baggy styles that are wide enough to go over them. Although a juxtaposition can look good too. There’s really no right or wrong.

Some do’s and don’ts of styling and wearing booties and jeans

When it comes to styling booties and jeans there are a few rules of thumb to follow. Whether that’s black booties with jeans or any other color. These styling tips will help you to get the most flattering looks and not have jeans bagging over your boots!

However, play around and see what looks best and what you feel the most comfortable in. As booties can easily make you look shorter if not styled correctly. Here’s how to not have them cut you off at the ankle:

Make sure your jeans are the right length

If you’re wearing your booties under your jeans, make sure the hem of your jeans is long enough to go over the top of the boots. This stops the issue of them getting stuck in the top of the boots.

I’ll sometimes pull socks over my jeans to keep them tucked inside the booties but not pull them up so high that they’re visible.

How to wear wide leg jeans with booties

Wide leg and Mom jeans work best over the boots and not under which can make your pants look like pantaloons!

Petite booties and jeans styling tips

If you’re petite try to make sure your jeans are long enough to go under or over the top of your boot fully. You want to avoid a gap of skin in between so that your legs don’t get cut off. I mean, that’s a look, but it’s not always the most flattering one. Unless you’re going for jean shorts and booties and then that’s totally fine.

When to avoid slouchy booties with jeans

As a general rule, avoid slouchy ankle boots if you’re planning on wearing them with anything but skinny jeans as they tend to be too bulky to fit under them.

Choose the right length ankle bootie for you

Choose booties that end at the skinniest part of your leg for the most flattering look. I look terrible in styles that go up to my calves as it just accents my muscular calves and the widest part of them rather than the slimmest part of my legs.

Get the outfit proportions right

Try to avoid wearing both baggy styles on the top and bottom and go for one or the other for a more flattering look. E.g. avoid wide leg jeans and oversized blazers and go for skinny jeans and an oversized blazer or wide leg jeans and a more fitted top.

How to wear booties with cropped jeans

Unless you’re really tall, a cropped pair of jeans is really hard to pull off with black booties or any color for that matter.

Shop the booties and jeans outfit edit

I searched for the best ankle booties and jeans to create all of the outfit ideas above. From flats to stiletto heels, black skinny jeans to distressed denim. Whatever your personal style there’s a way to make the ankle booties and jeans combo work.

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More how to style jeans & ankle boots ideas

Get more wear out of all of your jeans and boots or just get some fresh style and outfit ideas:

• 10 jeans alternatives that are comfy and fashion forward
• 25 best ankle boots | The womens boots & booties your wardrobe needs
• 25 White Jeans Outfits For All Seasons
• 15 Best Denim Shorts For Women AKA Jean Shorts For Women
• 31 Ways to Wear a Blazer With Jeans | Best Blazer Outfits