I LOVE Ankle Boots – you might have picked that up if you are a regular reader! I’ve written about them here and here recently, but I have had a few people mention to me that they still aren’t exactly sure when and where and how to wear them.

So I’m going to try, in my usual babbling way, and explain some of the different scenarios in which these little boots can be worn.

First off, some of the basic buying suggestions;

  • always start with black. They will be more versatile
  • a medium heel (cuban heel) is again, the most versatile. You should be able to wear it comfortably all day, but it will give you a little extra height, which helps no matter how tall you are.
  • buy good quality boots. In Winter, you shoes cop a lot – mud, puddles and the like. A good quality leather will last you much longer, and on the whole, be more comfortable too.

Three of the best to start with – here are three of my faves available right now in black.

Black Ankle Boots

SHOP THE BOOTS: 1. Witchery “Lois” boot $279.90 | Mollini black boots from StyleTread $199.95 | Country Road “Isadora” boot $229.00

Ok. Now that we’ve bought the right ankle boot, let looks at different ways you can wear them.

1. With tights and dresses

In Winter, treat a black ankle boot and opaque tights the same way you would treat a nude shoe in summer – use it to ELONGATE YOUR LEGS.

The ankle boot still allows the shape of your leg to be seen (as opposed to a knee high boot which makes your lower leg look thicker) so they are a more flattering cut when wearing skirts and dresses.

ankle boots with dresses

This works with skirts too. You always want to be elongating your leg, so the uniformity of black tights and ankle boots doesn’t break up your leg in too many spots.

ankle boots with skirts

If you wanted to expand your ankle boot collection, a nude or tan ankle boot works well with a bare leg and dresses in the in between seasons like so…..

nude ankle boots

2. With skinny pants

Now this is where I remind you that everything I saw is just a suggestion! Something to try, but of course, there is no wrong way to wear anything!

If you want to wear your ankle boots with skinny pants, you can either cuff your pants like so……

skinny jeans cuffed with boots

(even if you jeans AREN’T super skinny, try cuffing them over ankle boots – I ALWAYS wear my Boyfriend jeans cuffed with ankle boots) This still allows your to show off the most slender part of EVERYONE’S leg – your ankle.

boyfriend jeans collage

OR, if you pants or jeans are SUPER-skinny, you can totally tuck them into the tops of your ankle boots.

tucked into skinnies

This will depend on how skinny the pants are, AND how big the opening is at the top of the boots – but to be honest, don’t think TOO much about it! Both ways are right!


3. With draped pants

Ankle boots work really well with draped pants that taper at the bottom (ie. become thinner). They will tend to just sit on the top of the ankle boot (maybe a little bit tucked in). I find this is a great alternative look for jeans in winter. My feet are warm (because i can wear socks)

draped pants with ankle boots

See, there really are a HEAP of options – I hope that gives you a few more idea about HOW you can wear your ankle boots?

Any other tips? Tell me in the comments below, I’d love to know!

Until Next Time, In Love & Style Always