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How to Wear Ankle Boots!

A question I get a lot from styling clients is: how do I wear my ankle boots? I think there tends to be a lot of confusion around what length your pants should be when wearing an ankle boot, or if you can wear them with a skirt or not, etc. So as a result, a lot of people tend to just wear them with jeans because it's a simple solution. Thus beginning the all too familiar war on staying fashionable while keeping warm during fall.

I personally love an ankle boot because of how versatile it is! You can pair it with dress pants, jeans, skirts, you name it and you can probably make it work. However, there is a certain style of boot you can wear to complement your choice of bottoms but don't worry, I'll help you with that! Let's dive in!

How to Wear with Skirts!

Photo from @cellajaneblog

When wearing your ankle boots with skirts make sure your they aren't too wide around the ankle, this will create an illusion of cutting your legs off too short and is not a flattering cut with a skirt. Ankle boots that are wider around the ankle look better when paired with jeans.

How to Wear with Dress Pants!

Photo by @candicehuffine

The trick to wearing ankle boots with dress pants is to make sure your pant is the right length. This rule would apply with jeans as well, but contrary to jeans, your dress pants should be hemmed to the right length. Jeans can be cuffed when they're too long. I wouldn't recommend cuffing with regular pants because oftentimes the stitching and colour inside the fabric aren't the same as the exterior.

What is the right pant length?

You want the hem of your pants to end right at the top of your ankle boot, as shown in both the pictures above. If you're going to wear your pants with multiple types of boots at different lengths, try and fit them for an average height of all of them. If the hem falls a little past the boot or is a little short and shows some ankle, both of these scenarios are okay. The length you want to avoid is the hem falling to your heel.

How to Wear with Jeans!

Picture from @stylebyada

Similar rule than with any other pants, you want the hem of your jeans to be just above the top of the boot. Unlike regular pants, you can cuff your jeans to the right length! If you wear a boot that has a wider ankle with skinny jeans, you can definitely tuck the pant into the boot, however, this is the only instance where I'd recommend tucking your pant in.

Want more outfit inspiration? Give us a follow on Pinterest where we pin all sorts of outfit inspiration all the time! As per usual, send me a DM on Instagram if you need more help with your ankle boot outfits, I love to connect with you guys!

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