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How to Wear Ankle Boots With Your Pants – An easy guide

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Wear Ankle Boots With Your Pants

Ankle boots are a trendy shape of boot that has become a classic. They are indispensable in your closet and can look modern, current, kicky and fresh. They also run the risk of shortening your leg line and therefore making your legs look stumpy.  In addition, ankle boots can make your feet look chunky and cartoon-like. So how do you wear ankle boots without making your legs look stumpy? To this end, the answer is simple…show a little skin!

The way to wear ankle boots is to show some of your lower leg shape. Showing that your ankle or bottom of your shin is narrower than your pants and your booties helps to lengthen your legs instead of chopping them off as you would expect. This sliver of skin will visually elongate your leg because you are showing how narrow your legs really are. Revealing a small amount of your leg line keeps your feet and legs from looking disproportionate.

To this end, don’t pull skinny, straight or boyfriend jeans down over your ankle boots. Keep those hems ending above your ankle boots. This will create the styled and fresh look you are going for. There are many iterations of short booties: flat or heeled, fitted or wide open at the ankle, straight across the top or dipped at the front, above the ankle bone or below. Here is how to wear ankle boots with the leg coverings you already have in your closet…


Add a cuff to your pants in order to instantly create the ideal space between your legwear and your booties. Turn the hem up once to create a narrow or even a wide cuff. Keep in mind, a too-lengthy cuff can shorten the line of your leg. Check your silhouette in the mirror before you commit. If you do a longer cuff with skinny jeans or pants, it is easier if they have a lot of stretch to fit up your calf. You could do this wide one-roll with straight-leg jeans too.

A woman in black coat and black pants.

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A woman in blue coat and jeans holding onto a black purse.

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A woman in blue jacket and jeans holding a black bag.

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Alternatively, you could build a cuff with a double roll to ensure you are showing a little skin. The objective here is still to make a cuff that leaves a small space between the bottom of your jeans and the tops of your boots. This truly helps to keep your ankles from looking thicker than they are.

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A woman is holding onto her purse while wearing skinny jeans.

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Intentionally undone is the best way to describe this look. This messy finish gives the look an insouciant feel. It creates a casual impression for your outfit, like you care, but you don’t care. The definition of cool. Roll your cuff up in a larger cuff and then messily roll up again in a smaller cuff over the larger one. Or, roll your cuff up in a larger cuff and then messily pull the bottom edge of the pants a little way back down. Done, but then slightly undone.

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A woman sitting on top of a couch wearing black boots.
Mara Arnold by Juan


Your straight leg or skinny pants and jeans that end several centimetres above the top of your ankle boots are an ideal pairing. There’s no need to make that space with a cuff or roll because it is already there.

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A woman in black pants and a long coat.
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Cropped wide leg or cropped boot cut jeans are well-suited to ankle boots. This is a more fashion-forward look, certainly. Keep in mind that the space between the cropped pants and your booties should be no more than about 6 centimetres or your legs start to look chopped in half. That narrow sliver of leg skin helps keep your legs from looking cropped.

A woman in jeans and boots holding onto a bag

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A woman wearing jeans and a black cardigan.

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A woman in black jacket and jeans standing next to wall.

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A woman in black pants and red jacket holding a purse.

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If you are tucking your pants into your ankle boots, they need to be fitted quite snugly to your leg. Otherwise, you loose the lengthening effect and your legs can look stumpy. This means that this look is best with leggings that show off the shape of your legs. Many jeans aren’t tight enough at the ankle for this look to work.

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A woman in brown coat and black tights.

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When it is especially frigid outside, or if you are a person that is typically chilly, you can always wear a nude-for-you stocking or knee-high. Then when you are showing your shin skin, you will still be cozy.

Certainly, you can wear ankle boots with long, full length pants but then you lose the effect of the ankle boot. When your pants cover your shoe, no-one will see that you have ankle boots on. It definitely makes your ankle boots versatile and will decrease their cost-per-wear.

We love to help make these adjustments to the pieces you have in your closet. Try out our Essential Package and we will help solidify your style direction and remix your closet to match. You can always use us to build your wardrobe now or at a later date!

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