Sarah's Real Life
01. 10. 2014

how to wear flat ankle boots, how to wear ankle boots, how to wear wedge ankle boots, how to wear ankle boots with jeans, how to wear booties

It’s 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. I’ve learned so much since that first post. Most of it is about law, granted, but some of it is about ankle boots. So it seems like a good time to build upon last year’s advice. Welcome to How to Wear Ankle Boots (Part Deux)!

So. People seem to be wary of ankle boots for a couple of reasons. First, they’re worried they’ll look shorter and/or fatter because of how these boots are cut. Second, they just don’t know what to wear with the boots. I’ve said it before and I’ll say it again: The key to wearing ankle boots is elongating your legs as much as you can while still showing off the shape of the shoe.

Here are a few ways to wear ankle boots, and what to keep in mind along the way…

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I don’t know why cuffed jeans used to be a big fashion faux pas, but somewhere along the way things changed. Please. Do not be scared to roll ’em up. Roll or fold your jeans so the hem just barely hits the top of your boots. In case it isn’t obvious, this just applies to skinny/straight leg jeans. Don’t roll flared jeans – that’s crazy talk.

Keep in mind: This look should work well with wedge and heeled boots, but it can be a little trickier with flat boots. Ankle boots can easily make you look shorter, so if you’re already short (like me), just be really careful about proportions. And what about socks? That’s also a tricky issue. I think a peek of sock can be OK, but it can also ruin everything. You can play around with options, but if you want to err on the side of caution, I’d say stick with hidden socks.

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For shorties like me – and probably for most average-height ladies too – even chunkier ankle boots can work with skirts and dresses as long as they’re above the knee. Showing more leg makes your legs look longer, but let’s keep it decent, shall we?

Keep in mind: This shorter-is-better rule applies mainly to more casual boots, meaning ones with wider openings and chunky heels. A dressier ankle boot (like I’m wearing in the last photo in this post) is likely to work well with any length skirt!

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In case it hasn’t sunk in yet, making your legs look long and lean is pretty much my main piece of advice for pulling off these tricksy little shoes. Dark leggings are one of the most lengthening and leaning kinds of legwear I know of. In the photo on the left, I’m even wearing them with flat ankle boots.

Keep in mind: If I see you wearing leggings without a top long enough to cover your lady junk, I will yell at you in public, and it will be very embarrassing.

how to wear flat ankle boots, how to wear ankle boots, how to wear wedge ankle boots, how to wear ankle boots with jeans, how to wear booties

When it gets too cold out, you might not  want that sliver of exposed skin between your boots and the bottom of your rolled up jeans. That’s when tucking comes in handy. I sometimes put my socks over the bottom of my jeans so they don’t ride up too much.

Keep in mind: This only works with skinny jeans, otherwise it looks pretty tucking weird. Ha…get it?

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Some ankle boots are basically just pumps with some extra coverage on the top of your feet. When the boots are nice and fitted to your feet with narrow openings and thin heels, you can wear them with just about anything you would normally wear pumps with.

Keep in mind: All those other rules are just some tips to get you started. Depending on how daring you are with your style, you could very well break some or all of them! But I saved this for last because otherwise you wouldn’t have read the rest of the post. And I worked hard on it.

 

 

Mastered the ankle boot? You’re ready for your next challenge…

How to Wear Over-the-Knee Boots

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28 responses to “How to Wear Ankle Boots (Part Deux)”

  1. Hi Sarah, Love your post and the outfits you put together! Just not too sure about wearing jeans tugged into an ankle boot. I’d probably prefer the cuffed version. But that’s probably just me.
    Love & looking forward to your next post!

  2. ppfgirl says:

    Such a great & informative post here – and I love all these outfits!

  3. “Some ankle boots are basically just pumps with some extra coverage on the top of your feet.” When I first started to follow your blog, I swore off ankle boots. I thought, ‘Hey I’m 44. This is a younger lady trend.’ The more I saw your stylings, however, the more I warmed to them. Especially since I’m 5’8″! Then BAM here is this “how to” post. THANKS SARAH! I still haven’t made the jump but maaaaaaaaaayyyyyybe.

    • Oh yaaayyyy! This makes me happy. Be patient in finding your perfect pair and I’m sure you will learn to love them! I would tell you if I thought ankle boots were only for a certain age group, and I really don’t think they are.

  4. lalovesblog says:

    Awesome post!! I was so scared to wear booties at first but now I can’t stop wearing them!!! My collection has also grown a little over four pairs;)
    ~Lauren
    http://lalovesblog.com

  5. […] post has now been updated for 2014! Click here to see […]

  6. Great post! Very well written and thought out. I love ankle boots with everything as well :)

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    K.McCall
    http://www.TheUrbanFlamingo.blogspot.com

    xx

  7. Jenn Meadows says:

    I just bought my first pair of my ankle boots a few weeks ago. Thank you so much for your tips!

  8. are you seriously a shorty? Because in my mind you are like 5’8″! Thanks for the tips lady!
    xx
    Here&Now
    Enter my current giveaway!

  9. jess says:

    Hi! Youre blonde now! I love it, and i love your post on booties. I just passed up a great pair at target that youve seriously made me think twice about… 😉

    http://www.highheelstosneakers.com

  10. Hey there! This is the first time I’ve seen your blog and I have to say – love the outfits and this tutorial is great. I just got a new pair of ankle boots and I am looking forward to wearing them soon, so it’s quite timely for me. Good luck with law school. I’m a practicing lawyer in the midwest (since 2005) and I love being a lawyer, so don’t let people get you down with all the “life as a lawyer sucks, you’ll hate your job.”

    • So glad you enjoyed! I’m excited to hear how it goes with your new boots :) And thanks for the encouragement – I am still surprisingly optimistic about life even after 5 semesters of law school!

  11. Just stumbled on your blog – thanks for sharing this! I have the hardest time with ankle boot with dresses/skirts because my calves are very large so they look even bigger. If I don’t wear tights, they feel even larger.

    Alice
    http://www.happinessamidlife.com

    • Hey Alice, hope my pointers help! I’ve always had scrawny calves so I’m sorry if I don’t have the best advice on that topic. With skirts, I bet if you stick with boots like the ones I’m wearing in the last picture you’ll be OK. It’s when the top of the boots go above your ankle you might have issues with your calves looking too wide.

  12. Found this on Pinterest. I appreciate this post! I want to love ankle boots so much but am merely 5’6″! I now own a pair of HIGH heeled black ones, and lower to the ground (combat boot type) gray ones. I’m excited to try out your great tips!

    http://kenziescloset.wordpress.com

  13. I love ankle boots! Great post! :)

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

  15. Thanks for your ankle boot 101 post – coming from sunny singapore where is it sunny, humid and warm all the time, boots were a foreign footwear – never had a chance to wear them. Now that I’ve moved to Vancouver, they are a must in winter but I always find it hard to pair outfits with them. I bought some ankle boots that have been sitting in my closet for the past 2 years, I think I will drag them out now.

  16. […] current favorite blog is Sarah’s Real Life. I discovered her after searching how to wear ankle boots. And because of her I discovered Le Tote! (< affiliate) My first package is coming today and I […]

  17. […] seems I’m not the only one who can read a calendar, because the “How to Wear Ankle Boots” post I wrote back in January is getting a ton of hits this month, after a summer of not much […]

  18. Lynne M says:

    I am looking for some cut out ankle boots. I love the ones you’re wearing on the cover of this story. Can you tell me the brand or where they’re from?

    • Sarah H. says:

      Hi Lynne! They are Guess brand and I got them at DSW about a year ago. I don’t know if they’re still available but you can always check!