How to wear ankle boots: The Do’s and don’ts of booties

How to wear ankle boots


Ankle boots are to me, what a bob cut is to Anna Wintour, what pajamas are to B1 and B2, or like what Ryan Gosling is to 18-40 year-old women. They are probably (certainly) the most adored section of my wardrobe. If I could they’d rest on purple velvet cushions, sprinkled with glitter and dusted with baby’s breath, no exaggeration (yes, exaggeration).

WANT MORE: How to wear ankle boots between seasons

They’re incredibly comfortable, easy to wear and require minimal effort to style.

It’s for this reason that we’ve come up with this list of suggestions for the do’s and don’ts when it comes to styling ankle boots. Of course, you can totally ignore our advice and throw your computer out of the window, but we suggest you don’t because that’s both unproductive and a bit weird, but mostly because we have an awesome gallery chock-full of fabulous looking women sporting their favourite ankle boots. You know what this means? An excuse to buy more ankle boots (like we need one)

Gallery: How to wear ankle boots!

Image courtesy of, cover image courtesy of @ 

What are some of your boots do's and don'ts for how to wear ankle boots? Help out the sisterhood and tell us below!


  • Peta says:

    I love ankle boots, they really can be worn with anything. I am afraid I am a bit naughty though and my uggies do make it out of the house. Usually only to the servo or a dance class though. That’s allowed, right?!?

    • jessikins says:

      Me too. My uggies are pretty so I dont mind in someone sees me at the servo in them.

  • GMeers says:

    I wish I had cute uggies so I could wear them after pointe class when my tootsies need lots of TLC! :/ But I do have some ultra-cute suede boots that are pretty awesome and also much more public-friendly.
    I love the dress the model was wearing in the pic about not wearing skirts that end where your boots begin! :)

    • Brides says:

      Cotton On Body have a sale on atm, one pair of ugs for $25, two pairs for $30. I bought myself two pairs on the weekend. Cute enough and oh so comfy. 😉

    • I love how many Pro-ugg boot comments we’ve gotten on this post 😉

  • Chessor says:

    I only have one pair of booties, I’ve still not managed to convince myself that I can pull off the look. I will have to buy more pairs so that I can figure out more ways to wear them….did I just think of an excuse to buy more shoes??

  • Dana says:

    Very sensible and helpful tips! Thank you! And agree Ugg boots are not meant for public use!

  • Tess says:

    Love the comment regarding toe-less booties being inappropriate for Melbourne Winter! I was reading a style blog the other day encouraging the wear of toe-less booties “to show off your pedicure”, but like you said – blue toes ain’t a good look!!
    Ankle boots have quickly become a Winter staple for me and I love all the different styles and looks you can work with them :) x

  • Britt Chapman says:

    Love my booties and wear them with everything from leggings & cropped pants to skirts and dresses! I find that the ones that cut at the right spot on the ankle can actually make legs looks slimmer! Winning!! :)

  • thecatwhosawstars says:

    Totally agree that toe-less booties and winter do not mix. It is cool to be warm girls.

  • Beautynutter says:

    During the winter months I pretty much live in ankle boots, I have lots of pairs.

  • nettyballs says:

    i love ankle boots, i can never get them to work with jeans though, just tights and leggings!

  • Miss Rikki says:

    I spotted a pair of Spurr boots I liked today, boo for leaving the house with no money as a means of banning myself from spending. Did work though.

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