How To Wear Skinny Jeans With Booties 2021

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One of the most comfortable yet stylish fashion combos is a pair of skinny jeans with booties. However, many people have a hard time figuring out the best way to style the two together.


Are ankle boots still in style in 2020? HECK YES! That’s exactly why I’m sharing how to wear skinny jeans with booties with these 5 simple style tips. From date night to running errands, these easy yet fashion-forward combos will soon become a staple of your fall and winter wardrobe.

how to wear skinny jeans with booties

How To Wear Skinny Jeans With Booties

The types of jeans styles are almost endless – skinny, bootcut, straight, cigarette, cropped, boyfriend, girlfriend, and the list goes on. There are TONS of ways to style jeans but wearing skinny jeans with booties provides the most options.


Skinny jeans have been popular for years. While many other styles tend to look best on certain body types, the great thing about skinny jeans is that they look good on every shape. It’s no wonder they’ve grown in popularity.


Shopping for jeans is hard and anything that makes it easier is a win in my book. So, without further ado, let’s get into this list of the 5 most stylish ways to wear skinny jeans with booties.


how to wear skinny jeans with booties

Jeans (similar) | Tank Top | Booties (similar)Jacket


how to wear skinny jeans with booties

Cardigan (similar) | Jeans (similar) | Booties (similar)


1.) Cropped Jeans

If you’re wondering how to wear skinny jeans with booties, the easiest way is to go for a pair of cropped jeans. This particular style eliminates the need to play with the length.


When wearing cropped jeans, your height is the one important factor that comes into play. If you happen to be really tall, cropped jeans could end up being too short. If you’re of average height, finding a well-fitting pair should be quite easy.


Cropped jeans should show a small part of your calf but not too much of your leg. Typically, they fall slightly above your ankle, which is why cropped jeans are often referred to as ankle jeans.


how to wear skinny jeans with booties

Jeans | Cami| Cardigan | Booties (similar)


 Here are some cropped skinny jeans that are currently in stock with great reviews

Democracy Jegging Crop


High Waisted Skinny Crop


Mid Rise Skinny Crop Jeans


Do you wear socks with booties and skinny jeans?

This is a personal preference. Sometimes I do and sometimes I don’t. A lot of it depends on the style/cut of the bootie as well as the shape. I have some booties that are more comfortable with socks and some that are more comfortable without.

 how to wear skinny jeans with booties


The cut of some booties doesn’t allow for socks. However, if you’re looking for a great pair of no-show socks that can be worn with most booties, these are my hands-down all-time favorite. They don’t slip off the heel and they’re plenty low enough to be concealed. I wish I found them years sooner.

how to wear skinny jeans with booties

Booties (similar) | Jeans

 2.) Tucked In

Can you tuck skinny jeans into ankle boots? You can, but the amount of “tucking” is important. If done correctly, tucking in your jeans helps to create a leaner look while also elongating the legs.


You never want your jeans to be bunched up. If your jeans are entirely too long, tucking them into your booties probably won’t hide that. If this is the case, consider cuffing your jeans instead.


how to wear skinny jeans with booties

Sweater | Jeans | Booties (similar)


how to wear skinny jeans with booties

Booties | Jeans | Cami

3.) Single Cuff

The length of skinny jeans is important no matter how you style them, but it’s most important when cuffing. If the jeans are just a tad long, a single cuff is your best option.


A single cuff should show just a hint of your ankle. The ankle is the slimmest part of the leg and showing it prevents your legs from looking short and stumpy.


Cuff your jeans no more than 2 inches wide when going the single cuff route. If your cuff is more than 2 inches wide consider going to a double cuff.


how to wear skinny jeans with booties

Cardigan (similar) | Scoop Neck Tank Top | Jeans | Booties (similar)


4.) Double Cuff

The double cuff style tends to be more flattering in white or lighter-colored denim. Pairing your denim with a similar color/same color shirt helps to elongate the body and take away from the double cuff.


A double cuff, like a single, can make a shorter person appear stumpy. Choosing pieces that are the right color and proportions will alleviate this problem.


One rule of thumb for double cuffing skinny jeans: The skinnier then jeans, the tighter the cuff, the looser the jeans, the bigger the cuff can be. Since we’re specifically talking about skinny jeans in this post, you’ll want to keep the cuffs pretty tight.


how to wear skinny jeans with booties

Leopard Clutch | Jeans (similar) | Lace Cami


5.) Split-Hem Jeans

Split hem skinny jeans work best with booties and mules and they’re almost as easy to style with booties as regular skinny jeans. The main difference with split-hem skinny jeans is that you’ll want to pay attention to the length of both the back and front.


Some split-hem jeans have an even length all the way around while some are longer in the back than the front (as seen above). Typically, if the jeans are longer in the back you’ll want to stick with a lower shaft bootie. This keeps the jeans from covering the back part of the shoe. If you’re very tall you may not have this problem anyway.


You should always try to keep only a small section of your ankles showing when wearing skinny jeans with booties, but if you have split hem jeans with an uneven length, it will just be trial and error!


Split Hem Jeans – 3 Styles


 Split Hem Flare Jeans


Split Hem Straight Jeans


Split Hem Skinny Jeans


Can you wear jeans over booties?

Flare jeans and straight jeans look great worn over booties, as long as the jeans are wide enough. Check out these super simple yet sleek outfits below. A great pair of jeans and booties can easily take a basic outfit from boring to chic and you can still look put together while being comfortable.

Straight Jeans | Flare Jeans


how to wear skinny jeans with booties

Leopard Sweater | Booties | Jeans (similar)

How do you wear high booties with jeans?

Again, height is a huge factor when determining the best way to wear skinny jeans with booties. If you want to wear high booties with jeans and you’re tall, you can get away with several options:

1.) jeans tucked into booties

2.) cropped jeans

3.) single-cuffing your jeans


If you’re on the shorter side and want to wear high booties with jeans, your best option will likely be to tuck your jeans into your booties.


As you can tell from the photo above, I’m wearing high booties. If I were to cuff my jeans it would make my legs look about 1 foot long. If I were to wear a cropped pair of jeans, they would probably touch the top of the booties and still make me look stumpy. Cuffing would do the exact same thing so tucking my jeans in is the best option.


If you’re looking for more inspiration on ways to wear jeans with booties, check out some of these combinations below.

Jeans | Booties

Jeans | White T-Shirt Bodysuit | Booties

Denim Wrap Skirt | Booties

Embroidered High Rise Cropped Jeans | Cropped Boyfriend Jacket | Booties

Flared Denim Jeans | Volume Shoulder T-Shirt | Booties

Mid Rise Flare Jeans | One Shoulder Bodysuit

Jeans | Tank Top | |Booties | Earrings

Faded Jeans | Zebra Booties

Distressed Cropped Jeans | Sock Booties


I hope you found this guide on how to wear skinny jeans with booties helpful. If you have any questions or comments, feel free to drop a message below.


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Lauren is a wife, mom of 3, and personal trainer with a passion for fitness, fashion, and blogging. She shares affordable fashion finds, fitness tips, and helps you learn how to make money with YOUR blog!

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