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Old School Do or Don’t: Cowboys Boots and Dresses June 10, 2010

Filed under: Fashion — davissn30 @ 1:00 pm

For some reason, several of my friends are freelance writers in the NYC area.  And oddly, they all seem to know each other and be freakishly linked with me.  Try to figure out this one: my roommate’s hometown friend’s college friend’s writer friend is also my step-sister-in-law’s sister’s husband.  Whoa.

Which is totally not the point.  The point is I used to get all sorts of “Do or Don’t” requests from them for various magazines.  Like “Do wear white after Labor Day: Winter White is a real thing.”  Or “Don’t wear eyeliner on your bottom lid cause it makes you look whorey.”  That kind of thing.  So today, I have one of my own.  Do or Don’t: Wear cowboy boots with dresses and skirts that hit above the knee.  (Obviously, Linda Ronstadt and my mom in the 80s proved that the long skirt with cowboy boots is h-o-t, so that’s a non-issue.)

I am a proponent of the boot/dress look, even if mostly for utilitarian reasons: My cowboy boots are super comfortable, warmer on a slightly cooler day like today, and don’t make my feet reek like my slip-on flats do.  Plus, Connie Britton rocked the look on the season premiere of Friday Night Lights in May.  Sadly, I couldn’t find the full shot of her with her navy shirt dress and brown cowboy boot combo (which is, in fact, what I am wearing today), but here’s the top half of it anyway.

Also, watch Friday Night Lights.  It’s so good.

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[Updated: Not sure whether this weighs for or against the look, but a man on the subway platform stopped me to tell me that I had the prettiest legs he’d ever seen except for his.  Yeah . . .  First, thanks.  Second, no I really don’t.  Third, really?  You can only see about 3 inches of them.  How can you possibly tell?  Also, additional utilitarian use of cowboy boots: running from shards of glass swept up by frenzied cab driver.  Who knew?]