How to Wear Skinny Jeans with Ankle Boots

Co-authored by Candace Hanna

Last Updated: September 16, 2021

Skinny jeans and ankle boots look so good together it’s as if they were made for each other. The way you style your skinny jeans, however, can make or break your overall look. For example, wearing cropped or rolled up jeans looks better with ankle boots than scrunched up jeans. Along with styling your jeans, choosing the best boots for your desired style and the right outfit to match will have you looking effortlessly awesome.

Method 1

Method 1 of 3:

Styling Your Jeans

1
Pair cropped jeans with ankle boots. Cropped jeans are ideal for ankle boots. Choose a pair of cropped jeans that stop about 1 inch (2.5 cm) above your boots. You can wear jeans that stop 2 inches (5.1 cm) above your boots if you want a little more leg to show. If you don’t show any skin between ankles and boots, your legs will appear shorter.^{[1]
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2
Roll up the cuffs of your skinny jeans. If you bought your jeans cuffed, then great! If not, you can roll up your jeans that are slightly too long. The amount of times you roll up your jeans depends on how long they are and how much skin you want to show between your jeans and boots. You can choose to roll your jeans up only once or go for a double cuff, which is a good option for those who are petite.

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3
Tuck your jeans under to make them appear shorter. If you don’t want to tuck your jeans into your boots, it’s also an option to make them appear shorter. This works best if your jeans are only slightly too long. Simply tuck the bottom of your jeans into the inside of your jeans. This look will help you legs appear longer than they really are.
4
Tuck long jeans into your ankle boots. If your jeans are a little long, it’s an option to tuck them into your boots. Tucking your jeans works better if your boots are on the taller side for ankle boots—like boots that rise just above your ankles. Be sure that your jeans look smooth when tucked in rather than scrunched up or wrinkled.

Method 2

Method 2 of 3:

Choosing Ankle Boots

1
Choose flat ankle boots for comfort and style. Skinny jeans are the best choice of pants to wear with flat ankle boots. You can wear wear flat ankle boots with black pants and a blazer for a comfortable, yet dressy look. Or, you can wear your boots with jeans and a T-shirt for a casual, laidback style.^{[2]
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Wear black ankle boots to match a range of outfits. Black leather ankle boots are a great choice if you’re looking for a pair of shoes that will go with almost any outfit. You can pair your black boots with skinny jeans and a T-shirt, or wear them with your leather jacket and black jeans. You can pair your black ankle boots with just about any outfit other than a formal dress.
3
Go for boldly colored boots for a unique flair. A pair of boldly colored boots is all it takes to bring life to your outfit. For example, wear a pair of red boots with an all black outfit for a fun touch of color. Or, go for a yellow dress with purple ankle boots to be completely colorful.
- You can also wear boots with a design or embroidery for a unique touch.
4
Try buckled or laced boots for an edgy look. Boots are typically secured by zippers, buckles, or laces. For an edgy style, boots secured by buckles or laced up and paired with a leather jacket are all you need to achieve an edgy style. To take it a step further, wear ripped skinny jeans.
5
Wear low socks with your ankle boots. Since a little bit of skin should typically be seen between your pants and boots, wear low socks that don’t show over the tops of your ankle boots. You can wear regular ankle socks, or “no show” socks that are typically worn with flats.
- If you want your socks to show, wear a thin, dark pair of socks.

Method 3

Method 3 of 3:

Putting Together an Outfit

1
Go for a monochromatic look. A monochromatic outfit is great choice for a minimalist look. If your boots are black wear a black shirt, black skinny jeans, and a black jacket. For colored ankle boots, like blue boots, be bold and go for an all blue outfit!^{[3]
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2
Choose neutral colors for an everyday look. Neutral tones are great for a laidback, casual look. Choose a pair of beige ankle boots, with light-colored skinny jeans, and a tan or white shirt for a fully neutral look. Add a brown or beige hat as an accessory.
3
Throw on your winter jacket for a cold weather style. Long boots are usually associated with cold weather, but you can rock your ankle boots all year long. Wear jeans that can be tucked into your shoes, or wear thin, dark socks with your ankle boots for warmth. Then, you can wear a fur coat, long pea coat, or puffer coat, depending on your personal taste.
4
Wear your white jeans all year long. Break the rules and wear your white jeans after Labor Day. You can wear white jeans with black boots and a black T-shirt. Or, go for a more neutral look by wearing beige ankle boots, white jeans, a tan T-shirt, and light denim jacket.^{[4]
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5
Try a tank top and jeans in warm weather. A tank top, skinny jeans, and ankle boots is a cute and stylish outfit for warm temperatures. You can go casual with a muscle tank, ripped jeans, and ankle boots. Or, go for a slightly dressier look by wearing a patterned or plain halter top with black jeans and black ankle boots.

Expert Q&A
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Question

Do I need to tuck skinny jeans into ankle boots?

Candace Hanna
Professional Stylist
Candace Hanna is a stylist and style expert based in Southern California. With 16 years of experience in the corporate fashion and personal styling realms, she runs Style by Candace, a personal styling agency that focuses on helping individuals find their personal expression through clothing. Her work has been featured in magazines such as Shoutout LA and VoyageLA.

Candace Hanna

Professional Stylist

Expert Answer

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No! Showing your ankles can be sexy. When you're wearing ankle boots and jeans, it looks best if you can see a little skin between your ankle and the bottom of the jeans, especially around your ankle bone. Wear cropped jeans or, if you need to, fold the boots down a little. If the boots are higher, wear longer skinny jeans tucked into them.
Question

Should I roll my jeans with ankle boots?

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If your jeans are long, this is a good option. Roll up the cuffs once or twice so that the jeans end about 1 inch (2.5 cm) above the top of the boot. Keep the rolls narrow and tight so they look neat. If your jeans are short or are skinny enough to easily fit into the boot, you don’t need to do this (unless you just like the look of a rolled cuff).
Question

Can you wear ankle boots with cuffed jeans?

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Definitely! This is a stylish look that works well with ankle boots and gives your ankles a more slimmed down appearance.