How to Wear Ankle Boots

One of the questions that I get asked the most is how to wear ankle boots with skinny jeans.  The answer that I give is that you want the hem of your jeans to hit right at or above your boots.   You can accomplish this by either wearing ankle or cropped jeans that hit at or above your boots or by cuffing your jeans.

Cuffed Jeans

cuffed skinny jeans

wide cuffed jeans

You can either double cuff or single cuff your jeans.  Whichever one you do, I think it looks best if you see a little bit of your ankle between the cuff and the boot.  The single cuff is a little edgier and also looks good with new sock boots.

sock boots


Cropped or Ankle Jeans

cropped jeans

ankle jeans

ankle jeans

This is the easiest way to wear skinny jeans with ankle boots and the way that I do it most of the time.  I think ankle or cropped jeans look the best with every type of shoe, especially sneakers and heels.  Also, they are easier to tuck into tall boots.  Here’s some great ankle jean options to try:

skinny jeansrag and bone jeans at Nordstrom ($133) 


Caslon jeans

Caslon Ankle Jeans at Nordstrom ($79) – these have just the right amount of distressing and would work great with a taller ankle boot.


Express jeans

Express Jeans (on sale for $48)



I have also included some great booties.

black booties

ED Ellen Degeneres at Nordstrom ($98)


black booties

Sarto by Franco Sarto at Nordstrom ($100) – comes in black suede and many other colors



Vince Camuto at Nordstrom ($120) – also comes in tan and black


booties1.State at Nordstrom ($78) – these also come in black and red


I recommend wearing no show socks with these booties.  I prefer these and they can also be used with your sneakers.

no show socks

No Show Socks at Old Navy ($10)

I hope this has helped show you guys how to wear ankle boots with skinny jeans.  If there are any other fashion  or beauty questions that you have just drop me a comment and I’ll try to help.  XOXO Michelle



I've been obsessed with fashion and beauty since I was a little girl. I have always loved to help my friends shop and to give them beauty tips. I am so excited to have this platform to share my love for fashion and beauty with more people. I hope you enjoy this and get some great information at the same time. XOXO Michelle


  1. Thanks for sharing! I haven’t attempted to wear skinny jeans with short booties because of the look. Reading this post helped me know what kind of skinny jeans to wear now. Thanks!

  2. Your timing on this post couldn’t have been better for me, as I really like the look but haven’t quite figured out how to get it looking just right 🙂 Thanks so much for all of the helpful tips – I am off to the shops now to find a nice pair of ankle boots

  3. I saw this post in an email the other day. Thank you for the tips! I tried to be a big girl this year and bought my first pair of ankle boots, and then ran into the problem of how to wear what with them! This helped!

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