Sarah's Real Life
01. 26. 2013

This post has now been updated for 2014! Click here to see it.


It’s time for the long-awaited next installment of “How to Wear”! This time I’m talking ankle boots or booties. They’re so darn adorable, but they can be hard to wear. They cut off your legs at the ankle (as you might have guessed), which can make you look shorter, which in turn can make you look fatter. I don’t mean to speak for all women, but I tend to shoot to look more like Gisele and less like Danny Devito. The key to wearing ankle boots is elongating your legs as much as you can while still showing off the shape of the shoe.

Your ankle boot styling options depend on the kind of heel you’re working with, so I’ve split my examples into 3 categories: wedges, flats, and heels.

Wedge ankle boots


Wedge boots are my favorite so I put them first! You get extra height, which makes them easier to wear, but they’re still comfortable. I wear my wedge ankle boots with cuffed skinny jeans all the time. Skinny jeans make my short legs look as long as they’ll ever look (still not that long). But cuffing them a bit helps show off the shoe. If you have cropped skinny jeans, that would work too.


Wedge ankle boots can work with a skirt or dress too, as long as the hem falls a few inches above the knee. The more leg that’s showing, the longer your legs look. Just keep it decent, OK ladies?

Shop Wedge Ankle Boots: Save // Spend // Splurge

Flat ankle boots


Flat ankle boots are the hardest. They accentuate my lack of height, but I still love them! I wear them with cuffed skinny jeans just like my wedges. You’ll notice in both of the above outfits I tucked in my shirt – if you’re already cutting off the leg line at the bottom, you don’t want to do it at the top too!


Friends don’t let friends wear leggings as pants. Always cover your junk. That said, leggings can be very slimming on your stems, and you can get away with a short tunic. Flat booties with leggings can be a fun alternative to sneakers or flip flops with a super casual outfit.

Shop Flat Ankle Boots: Save // Spend // Splurge

Heeled ankle boots


Heeled ankle boots can be worn almost any way you would wear regular old pumps. They’re a great option for the winter because they’re a little sturdier than pumps and you get more coverage on your chilly feet.

Shop Heeled Ankle Boots: Save // Spend // Splurge

See more How to Wear posts:

Army Jacket     Oxford Shirt     Denim Jacket     Flared Skirt

20 responses to “How to Wear Ankle Boots”

  1. Cindy says:

    I would love for you to do a blog on The 6 Essentials that Should be Found in Every Closet.

  2. Tori says:

    I love ankle boots! If only I was brave enough to wear them! Your blog is darling!!

  3. Andrea says:

    I love all these pairings. They all look great !

  4. ashleigh says:

    I love wedge ankle boots! This is a great post.

  5. Great post Sarah – I’m short too and find ankle boots really tricky. I’ve bought two pairs and to be honest am not sure I bought the right ones! So hard to know in the store – love all you pics!

  6. The more you post about how to dress up flat footwear, the happier I am. I have a back injury and can therefore no longer wear heels at all. I was depressed about this for years and lived in running shoes, but, eventually, I got smart and just started buying nice flat shoes, sandals, and boots. I miss my heels, but at least now I have some variety.

    On another note, I’m short too and have never understood why women mind looking short. I like it. I think it makes me cute and I like that too. I own my stature with pride. My partner loves my shortness and always calls me a “boo, ’cause you’re just little!”

    • I’m a proud shortie too! I think I like flats just as much as heels, just depends on my outfit and mood and what I’m doing. If I’m going to walk very much, I don’t bother with heels because I know I’ll just get grumpy.

  7. Amanda says:

    Just saw your post and can’t agree enough about the problems with being short (although my mother always said “say petite”)! I have a couple of ankle boots and am always conscious of wearing them and looking shorter (read fatter), but your post now makes me appreciate their versatility. I will try again. Thanks heaps.

  8. ziainprint says:

    This is a really helpful post!! Thank you so much :*

  9. G says:

    i think the best look is when they’re paired with jeans! perfect for fall. thanks!

  10. quintanj1 says:

    You look great in all the styles of ankle boots, I love the ones with the print!

  11. Susie says:

    Love your work Sarah, and hope we can keep in touch, even though our connection wasn’t on the normal terms! Your work is amazing.

  12. Redzgurlz says:

    Great post!
    Love it!
    Thank you so much!

  13. […] been almost a year since I originally wrote about how to wear ankle boots. Back then I only had like 4 pairs, and now I have…you know…more than 4 pairs. […]

  14. […] How to Wear Ankle Boots (Sarah’s Real Life) […]