How to Look Super-Chic in Women’s Ankle Boots

Women’s ankle boots are stylish and convenient than knee high boots. They’re an absolute must in every fashionista’s wardrobe – adding to your Summer to Fall transition outfits, as well as showing more of your leg and fabulous hosiery!

Brown flat studded ankle boots

Ankle booties and boots are perfect for sporting that chic Parisian look and make it easier to move around, especially when you’re out clubbing. However, there are certain things that you should keep in mind when buying a pair of women’s ankle boots; on whether they would go well with your wardrobe as well as flatter your legs.

They can make short legs look shorter and wide legs even wider if worn incorrectly. You’ll have to work with your proportions, height and body shape to achieve a flattering look. On this page I’ll talk about some practical strategies, don’ts and do’s when buying a pair of womens ankle boots, as well as where you can buy them and how you should wear them.

How to Buy Womens Ankle Boots

 Scale them to your legsSelecting the right scale of boots for your legs, feet and ankles is important to avoid showcasing your size. Basically, a pair of stiletto heels will make full legs look like bricks in comparison; or if you have delicate legs and ankles then platform ankle boot heels will make them look like twigs. The size just becomes too obvious.

 Tips on how to get slimmer and longer legs in ankle boots:

catherine Zeta Jones wearing a top to toe black outfit with ankle boots


Match the boots with the color of the bottom (ex. black ankle booties with black or dark blue skinny jeans or leggings, tan boots on tan skin, black against dark opaque tights, etc.). Avoid mixing contrasting colors such as black on white as it will visually cut your legs in half.

Make sure the bottom is slim or tapered around the leg so that the hem looks slim and straight when tucking them in the boots.A little bit of heel slims your calves.

Stick to matté material textures such as leather

Shiny fabrics like patent will expand the size of your feet.Opt for womens ankle boots with minimal interest.

A lot of straps and buckles will make your legs look heavy. You should also try boots with visible zipper detail for a maximum slimming effect.

Select boots with a tapered/slim shaft

Although your ankles with look smaller, it may interrupt the streamlined silhouette we’re aiming for and drag your body frame down if you’re Petite and/or have short legs. Make sure the proportion of your outfit is rightThe taller the shaft of the boot, the shorter the skirt should be.

Kate Winslet wearing ankle boots perfectly, Sandra Bullocks looks shorter

Wearing a knee-length skirt with a taller shaft visually shortens the leg and gives you a chopped-off stubby look. This applies to dresses and shorts as well.

 Dress your body shape

We’re aiming for a well-proportional body shape. By knowing your body shape you’ll find it easier to pick fashion ankle boots that will flatter your body.

Also if you’re short and/or have short legs, avoid complicated details that make you look shorter.

Here are a couple of guidelines for each body shape:

Pear (heavy/wide bottom): Simple boot styles with a heel (eg. wedge) to avoid drawing too much attention downwards.

Complement the look with a short jacket, nice makeup or a pair of cute earrings Inverted triangle (heavy/wide top): 

Bright colored or embellished styles to visually “fill out” your slim legs and draw attention away from your prominent shoulders.Rectangle (little or no waist definition): 

Detailed boots because your goal is to add curves to your body frame.

Apple (round or wide torso): Same as inverted triangle. Complement the look with a belted cardigan or jacket.

Vanessa Hudgens wearing fringe ankle boots. No no for her petite frameVanessa Hudgens celebutopia

Avoid heavy and wide fringes on Minnetonka boots unless you’re tall and thin or a rock star. Your legs will look like clunky, wiggly human dusters. Need I say more?

 Bring life to your outfit with trendy boots

After securing the basic neutrals (womens ankle boots in black and brown), build on your boot-collection with various styles that reflect your personal style.Examples are suede ankle boots, wedge booties, bright colors, croc print, visible zipper details, studs, etc.Wedge ankle boots are definitely one of my faves. They boost your height without having to use your energy on balancing on heels – they’re fun and trendy too!


How to Look Chic with Womens Ankle Boots: Outfit ideas

There are many blogs and fashion stylists who have branded ankle boots as a tacky accessory, creating conservative rules such as “Don’t wear them with short skirts or you might end up looking like a hooker”. C’mon, we live in the 21st century! Let me give you some chic examples on how to wear them:

With a skirt adds a sassy twist to both your knee-length and short skirt. Ankle boots look trendy with casual jersey skirts as well as classy black just-above-the knee pencil skirt.Ankle boots with skirt outfits

I love how casual yet sexy a pair of brown flat ankle boots look together with denim shirt or a casual tee. A very wearable and flattering everyday outfit, even for those who don’t have a supermodel body. Opt for a right-above-the-knee skirt if you’re shy about your legs.

And another gorgeous party look I’ve seen on many famous fashion bloggers, is the from-top-to-toe-black outfit consisting of mini pencil skirt, black tee and black ankle booties. It’s a bit daring but it still looks balanced and chic.

The various textures (leather, jersey and caged booties are a joy to the eye. You might also want to throw in a pair of black sheer pantyhose.

Tip: If you’re conservative or shy about your legs, opt for a taller boot shaft and a pair of tights.

With a dress the same strategies for skirts apply here as well.

And don’t forget the proportion-rule as well – the taller the boot shaft thus shorter hemline is needed.

Ankle boots with dress outfits

I love how chic Gwyneth looks. The tunic shirt dress looks amazing with the tights and the matching accessories, and not least the chunky heeled ankle booties.

You can also wear ankle booties for parties and clubbing – but I prefer heeled ankle boots that have a short boot shaft that sits right below the ankles. Very leg-lengthening. Top it off with a matching belt for instant chicness!Oh, and avoid wearing ankle boots with a maxi dress at all cost!

With Tights and Leggings

A classic and effortless way to wear womens ankle boots. Hosiery makes it possible for you to wear your short dresses and long tops.If you decide to wear leggings with the boots, make sure that they’re not capris and that you don’t show any skin between the boot and hem – the tight pants-y just doesn’t complement the ankle bootie look. It looks silly.


Yes and no when wearing ankle boots with hosiery

I love how Rachel paired her brown ankle booties with black opaque tights, tee dress and knit cardigan. So effortlessly stylish.

With pants the best pants styles are tight or slim, which are easier to tuck in the boots. Here are some ideas with both bootcut and skinny jeans.

Skinnys Womens

Ankle boots are the perfect match for skinny leg jeans and pants. Just slip the bottoms into the top for a sleek look. If you’re not comfortable in skinnys then check out my tips below on wider hem pants.


Ankle boots with skinny jeans

No one wants the awkward bunches at the top (they’ll make your ankles look wide and chunky, by the way) with boot cut jeans.


The huge plus to wearing pants over shoes or taller boots is that you get ankle coverage without the bulk of a knee-high boot.

You can achieve a very attractive and classy look when wearing the ankle boots over the top of your ankle boots, disguising the short look of the shoes. Just make sure that the bottoms cover the top when you bending your knees.

Keira Knightley wearing bootcut jeans and ankle boots

Avoid pairing the boots with flare or wide leg – it creates an unflattering balloon effect. Slacks and boyfriend jeans can also be worn to expose a bit of skin, but the boots need to be short around the shaft, right below your ankles.


It looks fresh and stylish with a pair of denim shorts paired with a simple tee. I would also try this out with classy dress shorts as well.

Celebs wearing ankle boots with denim shorts

See how much longer their legs (Nicole Richie and Giselle Bündchen) look in shorter womens ankle boots? The wide and tall shaft on Kate Moss makes her look stumpy – even though she is a super model with long, slim legs.

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