They’ve become a footwear staple – the ankle boot.

But I still hear from my clients and other women I meet that they are confused about how to wear them.

Where should the pant hem hit? Do I cuff the hem or not? Can I wear them with skirts?

So, to clear up the confusion once and for all, I’m going to give you my favourite 3 ways for wearing ankle boots along with some do’s and don’ts so you can finally feel confident wearing this footwear staple.


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#1: When wearing ankle boots with skinny jeans, the jeans should either be very tight at the ankle (no bunching allowed) and tucked into the boot OR if they are slightly looser, cuff them. 


how to wear ankle boots, skinny jeans, with skinny jeans


If you’re wearing them cuffed, it’s okay to have a bit of skin (or a scrunched up sock) showing between the top of the boot and cuff of the jean.

Messy cuff, thick cuff, thin cuff, any one will do.

NEVER try to pull a skinny jean over top of your ankle boot though!

You can also do the ankle boot/cuffed jean combo when wearing a narrow straight leg jean or boyfriend style.

Just don’t do the cuff with any wider of a hem. So avoid any bootcut, flared, or wide leg styles.




#2: For work, swap out your predictable pumps for an ankle boot when wearing your favourite pencil skirt.



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Not only will it be comfier, but you’ll look super stylish!

Just make sure to go with a dressier boot. nothing too chunky or casual looking.

Also, if the skirt goes below your knee, you don’t want to lose too much of your leg line though – so the only rule is to make sure you wear a boot that dips down a bit in the front to show some of your ankle, or a boot with cut outs to show some more skin.




#3: For a playful and fun weekend look (or if you work in a casual or creative environment), ankle boots look great with fuller skirts!


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Again, to avoid losing too much of your leg line and making your legs look shorter, go for a boot that dips down a bit in the front to show some of your ankle.

If you are wearing a style of boot that cuts straight across the ankle though, make sure the skirt is above the knee so more leg is exposed.


So, what do you think? Are you ready to rock your ankle boots now?

I hope so!

If you need some encouragement or have any questions at all, request to join my private and FREE Style Society Facebook Group and I can help you out over there!

In the meantime,

Happy Styling!