How to Wear Ankle Boots

You Pick Wednesday

So, I know it’s spring in Chicago and for many of us our thoughts are turning towards sandals and open-toed shoes. But for anyone who is dealing with cooler temperatures this post is for you!

A reader recently contacted me and asked for help with a pair of ankle boots she just bought.





Here’s what she had to say:

My problem: So the Nine West store here had booties on sale. I loved a pair but as soon as I opened the shoebox at home, I started freaking out. Although I appreciate looking a few inches taller, these booties scare me to death LOL. What kind of outfit can I wear them with?

I bought my first pair of ankle boots in fall 2011.


Admittedly, I didn’t know what to wear with them, either! But it turned out that they are quite a staple in my wardrobe now. So here are my suggestions on how to wear ankle boots.

1. Putting them with black tights or even sheer black textured tights/nylons will help ease you into wearing ankle boots with skirts and dresses.

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2. If you like the look of bare legs with booties, you could wear them with a skirt and no tights.

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3. Wear jeans or pants over the top of the booties.

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4. Tuck skinny jeans into them or roll the bottom of the jeans up so they hit the top of the booties.

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Want more ideas? I have to give a shout-out to Katie from Alaskan Weredork who does the best job I’ve seen of wearing her many pairs of ankle boots with almost any outfit you can imagine.

Do you have ankle boots? How would you wear them?


Don’t forget you can always submit your own questions for You Pick Wednesday!


12 replies on “How to Wear Ankle Boots

  1. Bethany @ Accidental Intentions

    LOVE THIS. I have two pairs of booties that looked super cute when I bought them, but I rarely wear them because I’m always unsure HOW to wear them. I’ll wear them under pants sometimes, but it seems like a waste to hide all the cute details of the shoes under pants, you know? So thanks for this!

  2. kilax

    This is so helpful! I don’t have these types of boots, but I really like the black on black look! And of course, duh you can wear them UNDER something (never would have thought of that). 🙂

  3. Joules

    You’re rocking the booties! I personally like them best with tights or without tights under a pretty dress. 9to5chic wears them REALLY well in some of her older posts.

    Also, they’re perfect for our crappy rainy weather today! (I’m a Chicago girl, too)

    Style by Joules

  4. Katie of Alaskan Weredork

    Hah, and I was reading this going “yay, pointers on wearing ankle boots!” (Thanks for the totally sweet shout out, that was way too kind and I just realized that I probably have way too many ankle boots.)

    I still need to try out a version on your printed dress with the ankle boots, it’s such a cute look! (I also really like the first picture of #4, it’s so sleek looking and pretty with the cardigan.)

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