Ways to Style Ankle Booties

Ways to Style Ankle Booties

What should you wear with booties? A cold-weather staple or summer fashion statement, ankle boots are as cute and versatile as they are popular. But, not all booties are created equal. With so many shapes, patterns and styles to choose from, it can be hard to know which is perfect for your style and wardrobe. Or, if you've already got a pair or two in your arsenal, you may be wondering how to complement them with the right cut of jeans or skirt hemline.

In this guide, we'll help you learn everything you need to know about short style boots, so you can walk out the door looking fresh all season long.

Before You Buy, Know Your Booties

With so many options, it can be challenging to know how to style ankle boots. Everything from the tip of the toes to the fit of the leg can change the way the boot looks and what you should wear it with. If you're in the market for a new pair of booties, there are four things to keep in mind:

1. Height

The height of an ankle bootie generally refers to how high it goes up your leg. A short ankle bootie might hit the skin just above the ankle bone, a medium ankle bootie will start to make its way up to your shins and a high ankle bootie might reach just below the thickest part of your calf muscle.

Depending on the width of the ankle, a high ankle bootie will look best with wide-legged jeans and pants. You might also find success tucking them into fitted legged pants, although you may find some bunching around the ankle.

A medium ankle boot is your go-to for all things skinny. Both leggings and skinny jeans will shine in a medium-length bootie — you can feel free to tuck, roll, and crop to your heart's content.

However, figuring out how to wear low ankle boots is another story. A short ankle boot can support skinny jeans and leggings, although they are too low to tuck into. So, if you plan to wear short ankle boots, you'll need to either roll your jeans or pair them with wider-legged pants.

2. Ankle Width

To determine your shoe's ankle width, look at the shape of the back of the shoe just above the heel. Does it have a form-fitting build that hugs your foot, or is it a bit chunkier?

All sock booties have a thin ankle, although plenty of broader shoes are also considered thin. Thin-ankled booties make a big splash with wide-legged pants, as they accentuate the hemline well.

You'll have trouble pairing a wider ankle with a wide-legged pair of jeans, as this may create an awkward shape around your ankles. But, a broad ankle is the way to go if you want to tuck in a pair of skinny jeans and avoid bunched-up fabric.

3. Toe Shape

Most ankle booties will have either a rounded or pointed toe, and some have a squared toe. In general, a pointed toe offers more of a dressed up, professional look, while rounded toes provide some extra comfort, and look great with a comfy everyday outfit. 

4. Shoe Pattern and Color

Shoe Pattern and Color

Neutral, bright or patterned? Solid colored booties in brown or black will be your most versatile options. They can be dressed up or down and worn with either solid colored or patterned blouses and bottoms. 

A brightly colored boot in a red or a white can truly pop against an all-black ensemble, leather pants or another neutral bottom and top combination. If you're looking to make your shoes the star of the show, a patterned bootie is the way to go. 

Tuck and Roll: How to Wear Ankle Boots With Skinny Jeans

So, what do you wear with ankle boots? When in doubt, go with skinny jeans. Form-fitting jeans and ankle booties are the makings of a classic outfit. But this winning combination can be a bit confusing without a little practice. Some jeans won't look good tucked into an ankle boot, while others might be too cropped to pair well with a shorter boot. Here are some quick tips to get the look you're aiming for:

Avoid the Dreaded Ankle Bunch

If your jeans are full-length, you might have trouble tucking them into your boots. Both high and mid-height boots can look great tucked, but they tend to bunch up. The best way to avoid this is with a tight-fitting pair of jeans or a wider boot. 

Rolling In and Out

If tucking in just won't do, you can opt to roll your pant legs in or out.

Rolling out will reveal the inside of the fabric, which might be a different color, depending on the dye. Cuffing your jeans is a great way to spruce up a casual look, so roll them up when you've got a relaxed boot to match. Avoid rolling up your pants with taller ankle boots, as this looks best with mid to short ankle boots.

Rolling in or under will hide the hem of your jeans, which can help you achieve a "tucked-in" look without the messy bunching that comes with it. Rolling under looks more polished and professional than cuffing, and helps to elongate the leg. A rolled-inward look is absolutely the way to go with taller boots.

Shop Till You Crop

Of course, you can avoid the roll or tuck dilemma altogether by going for a cropped pair of jeans. The key to pulling off the cropped jean look: make sure the hem of your pants stops at or just before the top of your boot. If it ends just before the boot begins, you'll leave some of your legs visible. Limit this to about two finger-widths or less of bare skin between the hem and the boot for the best effect. 

Comfy and Casual: How to Wear Ankle Boots With Leggings

The good news about leggings is that any pair of boots outside of sock booties with a tall height look stylish and fun. Because leggings are worn flush against the skin, they look great tucked into practically any bootie. If you're looking for a fab outfit to go with a pair of wide-ankled boots, leggings are the way to go. Here are a few of our favorite legging and bootie looks:

Snakeskin Chic

Animal print booties are a fun way to combine business and pleasure. While the color palette is neutral, the pattern lets you walk on the wild side. Or, you can pair some nature-inspired leggings with a solid colored, neutral-toned bootie, so the attention stays on your statement piece.

Black and Shiny


We're all for faux-leather pants for a fun night out. The look couples well with a pop of color, like a bootie in candy apple red or an electric blue. But, for a more down to earth vibe, you can pair a faux-leather legging with a black suede boot and a comfy sweater of your choice

Want to know a secret? You don't need faux-leather to complete this "out on the town" style. For a stretchy and comfortable alternative to faux-leather fabric, try some black snakeskin leggings. 

Layered With Leggings

Another playful way to assemble the legging and bootie power-duo is adding an extra layer: socks. Cropping or rolling your pants in the winter months is out of the question. We recommend a neutral-colored sock to avoid drawing too much attention to your feet and going for a cropped or shorter pair of socks to avoid bunching. Your socks should be visible above your boot, but shouldn't reach higher than a few inches. 

Try fuzzy socks for cold-weather comfort, which pair well with black or animal print booties alike. To keep your legs just as warm as your feet, style this look with a pair of fleece-lined leggings for an outfit that will keep you warm all day.

Wear With Flair: How to Wear Ankle Boots With Wide-Legged Pants

If you're at a loss for how to style short boots, try some nice wide-legged pants. The wide-legged pants trend that rose to fame a few years ago is holding strong. If you're tired of tucking, wide-legged pants are a stylish way to wear your booties. Short boots are a must for anyone looking to rock a pair of wide-legged pants, so here are a few fashion tips:

Ankles Away

Just like with cropped skinny jeans, be mindful of how much ankle you want peeping out. You have a bit more leeway when you've got a flowy hemline, but it may start to look funny if you're showing more than a few inches of your legs with a pair of wide-legged jeans.

The key to pulling off ankle boots with broader pants, whether you reveal a bit of skin or not, is to pay attention to the width of the ankle. With wide-legged pants, the tighter the ankle, the better. You never want the opening of the boot to look thicker or as thick as the cut of your pants. So, if you are wearing a pair of straight-legged pants or boyfriend jeans, your best bet is a sock bootie or one with a tight opening at the top. With cropped flared paints, you can get away with a looser fitting pair of boots, but still, try to steer clear of wide-ankled boots.

Tie It in a Bow

A truly inspired look for those seeking a wide pant style is a ribbon waistband. You can pair them with an extra-short bootie, and you don't have to fear that wider-set heal. If you've been hesitant to jump on the wide-leg pant train, you can try a tapered pair of pants for the best of both worlds. 

Culottes, Culottes, Culottes

Whether you call them culottes, gauchos or just cropped wide-leg pants, they're an all-star trend ripe for an ankle bootie pairing. While you still may want to avoid a wide ankle bootie, you can get away with a semi-wide ankle, thanks to the broader, flowing hemline.

You'll feel just peachy in some corduroy culottes, which balanced with neutral gray or tan booties will make any outfit stand out. Looking to go even shorter for a dapper summer flair? Try airy gray culottes matched with a short brown or light-tinted boot.

If you decide to wear gauchos to the office, it's best to limit your skin exposure. We recommend pairing a professional black culotte with a pair of taller, thinner-ankled booties.

From Midi to Maxi: How to Wear Ankle Boots With Dresses and Skirts

Booties and skirts are a match made in heaven. The hemline of a dress or skirt makes any bootie look great, no matter the height of the boot, point of the toe or width of the ankle. If you've got a pair of booties that don't seem to look right, you can wear them with confidence with almost any skirt:

Fitted and Fab

Fitted and Fab

If you prefer a tighter fitting dress to a looser one, you can still rock practically any bootie you have in your closet. Try a rounded toe with a shorter fitted skirt for a casual style, or a pointed toe paired with a textured fitted skirt for classy occasions.

Flowy and Floral

Whether you are a pretty in pink kind of girl or looking for a bolder look, you can find your style with a floral dress and booties. Just like fitted dresses and skirts, you'll be hard-pressed to find a bootie that doesn't look great with any floral dress you own.

For a cute and feminine appearance, try a delicate flower-covered dress with a mauve, gray or tan boot. If you want something more daring, pair a dark-colored floral dress with a shiny or suede black bootie.

Socks and Stockings

Can you wear tights with ankle booties? Definitely. You could even winterize your favorite dress or skirt with a pair of fleece-lined tights and booties.

But, if you don't want tights, you can also go with socks for a dressed down, cozy look. Try wearing a pair of brown or neutral socks under booties paired with a skirt — perfect for early fall.

Style Your Boots Your Way at My Sister's Closet


At My Sister's Closet, we believe you can wear ankle booties all year long. They're a classic fashion piece that can be dressed up or down, so you can be prepared and have fun at any occasion. As long as you take the shape of them into account, you'll have no problem figuring out what to wear with ankle boots.

If you're looking for a new pair of booties or an updated wardrobe, check out My Sister's Closet. Looking for more style tips? Browse our newest arrivals for the most fashion-forward pieces.