The Thigh High Boot Challenge

They’re sexy, scary and a great excuse to not wear pants — but are they cool?

11.19.16

Leandra

Thigh high boots are like a cashew in that they trick their consumers into thinking they’re one thing (a nut when they’re really a fruit, a practical shoe decision when they’re anything but), then following use they pose the philosophical question of: Huh? 

As in, did I really just eat 51 cashews a.k.a. 51 individual fruits, or am I emulating Julia Roberts in Pretty Woman during the former half of that movie, and is that an acceptable role to play through the motions of my psychic architecture, respectively?

I know, I know, I should just drop the mic now but of course, I’m not going to do that. Instead, I’m going to go on and on and on (and on) — and then let Amelia do the same — about a challenge that was self-imposed and consequently accepted this week. Following actionable curiosity about thigh high boots (call it fascination of the abomination: you hate them, you hate them, you can’t look away, you want them, you need them, you get them, you’re confused — now how to wear them), we set out to figure out just that: how to wear them. Follow the slideshow + comments above to read some equal parts reductive and emotional sentences about how the boots makes us feel — plus some verdicts.

Oh, and happy Friday!

Amelia

Cashews are low on my nut list so allow me to throw out another metaphor, this one situational: remember in middle school when you had a suspicion that something was cool, but because you were at an “impressionable young age” and needed the confirmation of others, you kept quiet and didn’t tell anyone? That’s how I felt about thigh highs. They seemed sexy and trendy (see: shoepants) and hard to pull off — but were they cool? Fashionable as opposed to hot.

You’d think that if I’ve learned anything by now, it’s that “cool” is a state of mind. But it’s also a state of styling. If you harbor hope for a sartorial something then rarely is it a lost cause. You know the cliché: if there’s a Will, there’s a Grace.

There’s also a way. If you’re trying something scary, build the rest of your outfit in the same way you would regularly and your risk won’t feel so strange.

See what I/we/us/yee(zy) mean(s) in the slideshow above.

Then party.

Photographed by Krista Anna Lewis

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