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5 Ways To Wear Thigh-High Boots This Winter - Fashionista

5 Ways To Wear Thigh-High Boots This Winter

Ranked in difficulty, from easiest to "eek!"
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On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

Over-the-knee, thigh-highs... call them what you will, but there's no denying the appeal of this winter's most dramatic boot style. There is also no denying that part of that appeal lies in the style's innate subversiveness. 

Maybe that's because OTK boots have a long history of provocation. Well before Julia Roberts wore her iconic shiny vinyl swashbucklers in the 1990 film "Pretty Woman," women were using them to turn heads. Back in the 19th century, theatre actresses wore them onstage to show off their (usually hidden) legs, hoping to draw bigger crowds. It's no coincidence that by the time the boots made their fashion debut on the runways of Balenciaga and Yves Saint Laurent in the early '60s, the youth subculture and a more liberal attitude toward dressing was starting to explode. A decade later, raffish "It" girls like Jane Birkin had made the style a quintessential part of the '70s look.  

So, where does that leave us now, in a time when nearly anything goes and nearly everything — including OTK boots — is available in every incarnation imaginable? It leaves us with lots more options, sure, but also with lots more ways to be confused. How the heck are we supposed to wear these enticingly provocative yet on-trend boots in a way that embraces their innate power and sexiness whilst still feeling classy and stylish, and not totally over the top? 

The answer, as with most things, lies somewhere between portraying total confidence and the attitude of IDGAF. But in case that's too abstract, we've broken down five ways to wear the trend right now and ranked them in order of difficulty from 1 to 5, with lots of handy tips sprinkled throughout. Check them out, below.

With a Midi 

Difficulty Level: 1

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

Arguably, one of the best reasons to wear thigh-high boots in the first place is to keep your legs warm, and this look lets you do so comfortably whilst also looking cool. It's one of those rare occasions in which function and fashion meet; a style unicorn! And it's relatively easy to pull off, too.

To avoid feeling frumpy, choose a dress or skirt with an A-line shape and boots with a slender toe and bit of a heel. Play around with coordinating or contrasting colors and textures — try suede boots with a silky dress, perhaps, or a twill wrap skirt with tonal leather boots. Since you're not showing any skin, you've got some room to experiment.

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With Jeans

Difficulty Level: 2

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

This look is pretty easy to pull off, as long as you don't mind that the focus of your outfit will be somewhat on the crotchal region of your body. With that in mind, the fit of the jeans is pretty important. For obvious reasons, you'll want a skinny cut (it's a lot harder to cram a flare into a boot) and you really, really don't want anything remotely resembling camel toe. This might be the perfect time to break out those slightly stretchy skinny jeans you haven't worn in ages. 

Speaking of which, skinny jeans look great with something boxy on top, so do that. Try a big, chunky sweater. Or, this season's ubiquitous puffer jacket, perhaps?

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With a Girlie, Knee-length Dress

Difficulty Level: 3

On the street at spring 2017 Milan Fashion Week. Photo: Imaxtree

On the street at spring 2017 Milan Fashion Week. Photo: Imaxtree

Pairing something delicate (a girlie dress) with something tough (leather boots) is an aesthetic no-brainer. But to really get this look right, pay careful attention to the amount of skin peeking out between the hem of the dress and the top of the boot: Choose a dress either skims the top of the boots or hovers ever-so-slightly above to reveal just a sliver of skin.

But a word to the wise! Without tights, you run the risk of 1) getting cold and 2) accidentally flashing everyone when the wind blows. Some people may not care about that kind of thing, but if you do, wear biker shorts underneath. 

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With a Mini and Tights

Difficulty Level: 3.5

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

On the street at fall 2016 New York Fashion Week. Photo: Imaxtree

This leggy look isn't actually that tricky — as long as you keep a few things in mind. First, you've really got to love your thighs. They're the stars here. Second, you'll want very opaque tights in a shade that matches your boots. This helps create one long, lean line. 

After that, it's just a matter of finding the right skirt: Tweed, wool, leather or denim give the look structure; and silhouettes with a slight A-line are the most flattering for legs and hips.

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With a Short, Slouchy Dress

Difficulty Level: 5

On the street at spring 2017 Milan Fashion Week. Photo: Imaxtree

On the street at spring 2017 Milan Fashion Week. Photo: Imaxtree

Okay, so there is a lot of thigh skin showing here. These sweatshirt dresses are short. Normally it would not be considered "classy" or a "good idea" to wear a super-short dress with high-heeled, thigh-high boots. But that's not really the point here. This is really more about being irreverent and cheeky. High-low. That sort of thing.

That said, the sweatshirt dress-thing needs to be oversize and slouchy. It should not, under any circumstances, contain Lycra or be body con. It should be big and look like maybe you stole it off your boyfriend's very clean, very expensive floor.

If the hem of the dress hits at or below your fingertips, this look isn't actually all that risqué. (See above, right.) Still, proceed with caution! For most of us, this is definitely NSFW. It's just way too casual, exposed thigh skin or not. So, if you do decide to go this route, do it off the clock. Awkward meetings with HR aren't fun for anyone.

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