How to Rock Thigh-High Boots

Thigh-high boots. For some, they’ve become a staple in their fall and winter wardrobe. For many others, they’re intimidating as Hell. For whatever reason, there’s a lot of “rules” that surround thigh-high boots. These rules, like most fashion rules, are pretty arbitrary and unnecessary. One magazine will say you have to posses giraffe legs to successfully pull off a pair, which is not humanly possible, while a sales associate will say you need to buy a designer pair to really make your purchase worth it. Give us a break.

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As you know, we’re all about rule breaking.With just a quick peruse through our Pinterest board (above), you’ll clearly see that there are tons and tons of different ways to rock thigh-high boots. It doesn’t matter what so and so magazine, blog, or bitchy drunk girl in the bathroom told you, because whoever you are, no matter your style, body shape, lifestyle, whatever, you can rock thigh-high boots if you want to.

However, before you do, here’s a few important style tips to keep in mind:

1. Play with Volume and Texture

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Taylor Tomasi Hill

From suede, leather, vinyl and more, thigh-high boots can come in a lot of different textures. A fun way to play off the texture of your boots and make your look more interesting, is by pairing them with contrasting fabrics. For example, if your thigh high boots are made from a sleek leather, pair them with an oversized, chunky and fuzzy sweater dress. Or, mix a few contrasting separates together to create a multi-dimensional look (like the one pictured above). Play around with fringe, faux fur, even neoprene, and see what comes of it.

Separately, but equally as important as texture: play around with the size and width of the pieces you pair with your thigh-high boots. Once again, because thigh high boots are so sleek, you can pair them with massive pieces on top, and they’ll balance each other out.

2. Pair Them With Tights or Thigh-High Socks

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Since all the attention is bound to be on your legs anyway, wearing thigh-high boots is a great time to play with fun and bold hosiery (that’s the fancy word for tights, nylons, socks, etc.). You can keep it simple (like the photo above) and pair your thigh-high boots with a contrasting pair of socks. Or, you can be a little bold and pair them with printed tights or socks. Whatever you do is totally up to you, and will probably look good, because, done in good taste, this is essentially a fail-proof style tip.

The best reason to pair your boots with socks or tights, though? Extra warmth. Thigh-high boots do more than just look super cool. They can actually keep your legs really, really warm during the winter. An added layer underneath your boots just adds to this warmth and makes your outfit a little more dimensional.

3. Keep it Monochromatic

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Ashley Madewke of Ring My Bell

Naturally, you can wear your thigh-high boots however you damn well please. But, if creating a super-chic look is something you’re super into, then we suggest playing around with a completely monochromatic outfit (aka a look that consists of only one color).

The way we see it, you can essentially approach wearing thigh-high boots a couple ways. 1) You can go all out. Thigh high boots are already pretty wild, so you can play off this and wear an entire outfit that is bold and fun. Or, 2) you can keep it simple. A monochromatic outfit actually falls in the middle of these two style-extremes. It’s a safe, yet, not necessarily typical styling choice, and it’s a good way to comfortably ease yourself into wearing thigh-high boots.

4. Keep it Short

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Louise Roe

As you’ve probably already noticed from the number of photos in this post, thigh-high boots pair really well with short hems. So, pull out that 70s-style mini or bottom-grazing sweater dress, that are usually reserved for a night-out, and pair them with your sassiest pair of thigh high boots. Because thigh-high boots are so, well, high, you can get away with pairing them with really short pieces/pieces with a high slit. The boots will actually end up covering a majority of your legs, and while you can totally wear them with longer bottoms, they look exceptionally good with shorter pieces.

It’s like styling a crop top, in a way. Sure, you can pair a crop top with a bottom that sits lower on your waist and you’ll show your midriff, which is fine. Or, you can pair your crop top with a super high waisted skirt or pant, so there’s just a sliver of your skin showing. This technique, whatever it’s called, is sexy in a very subtle and tasteful way.

5. Elevate Your Basics

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As killer as thigh-high boots may look with an edgy outfit, they can be just as cool and stylish paired with a more casual look. Use your thigh-high boots as an opportunity to elevate your band t-shirt and denim. An oversized cardigan, tank and leggings may be your go-to lazy day outfit, but throwing on a sleek pair of thigh-high boots transforms that look into a semi-polished one that can be worn going out for coffee or meeting a friend for lunch.

Basically, what we’re getting at is that thigh-high boots are actually a lot more versatile than they may originally seem. They may seem like a frivolous piece that won’t get much wear, but you literally can wear them with whatever you want if you’re creative and daring enough, which leads us to…

6. Be Daring

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Beyonce Knowles attends the Costume Institute Gala for the “PUNK: Chaos to Couture” exhibition at the Metropolitan Museum of Art on May 6, 2013 in New York City. (Photo by Dimitrios Kambouris/Getty Images)

The biggest issue people have with rocking thigh-high boots is that they lack the confidence to do so. Thigh high boots are not for the faint of heart. They’re a statement piece, and justifiably so. People pay attention to you when you wear them, so you have to be prepared to channel your inner Beyonce, and be comfortable in your style convictions and decisions to accept those stares and head turns. No matter what tips or tricks you follow (even the ones we’ve listed above), you will not successfully rock thigh high boots if you do not think you can. You need to own the fact that you’re daring and bold enough to pull off the look and you will.

What tips and tricks do you have for styling thigh-high boots? Leave your answer in the comment section below! 

Emma Klug started The Style Note in the fall of 2012. Her writing has been featured in DBusiness Magazine, Chicago Sun-Times, Nothing Major, The Working Wardrobe, Chicago Talks, Inexpensive Chic, and The Wayne State University student paper: The South End. When she’s not writing you can find her eating pizza, binge-watching Netflix and working her day job as a magazine editor.

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