How to Wear Ankle Boots (Part Deux)

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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 causal 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.

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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.

Follow my blog on Bloglovin’ or Facebook to see future boot-tastic outfits (and some other fun things too).

See more “How to Wear” posts:

Army Jacket     Oxford Shirt     Denim Jacket     Flared Skirt

26 thoughts on “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. “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.

  3. Pingback: How to Wear Ankle Boots | Sarah's Real Life

  4. 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.”

    • 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.

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  6. 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.

  7. Pingback: Skinny Sometimes | Great Eats, Little Feats & Things I Find Neat #17

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