styling plaid

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This past weekend, a friend and I indulged in some retail therapy, to help us through the crazy week. I came across this plaid skirt and fell in love with it. Maybe it’s the fact that I wore plaid for twelve years (although the uniform shirt was markedly less flattering than this one), but I’ve been looking for a plaid skirt for a few months now, and was delighted to finally find one. But then I started to wonder if I would really wear it. Would I find myself pulling out knee socks, or my letterman’s jacket, in a desperate attempt to make it work?

The thought had no more crossed my mind, when a good old competitive spirit reared up. Challenge accepted. I was running through different ideas in my head and finally settled on my favorite three. They may or may not be titled after a musical, a movie, and a TV character, but it’s fine.

No. 1: Heathersplaid skirt, black booties, sequined tee

I know, I know, Heathers was a movie before it was a musical. But why angst about your problems when you can angst and sing about them? If you haven’t heard of Heathers, it’s basically your typical story about cliques and high school drama, just with the casual addition of murder. Mass murder, I should say. Why on earth I ended up trying to mirror that style, we may never know. Maybe my rebellious stage is hitting late, maybe I just wanted an excuse to sneak Broadway into a post (defs the latter). Edgy isn’t a look I can generally pull off, but this look helps me fake it. We’ll update the classic skirt with some sequin accents, while the heeled boot helps out the silhouette. As I’ve said before, sequins/glitter aren’t a look I’m generally inclined to. But give a girl the right skirt (and the right cast album), and she might just make it work.

No 2: Ordinary Peopleplaid skirt, wool sweater, brown heeled boots

Along a similar theme, yes, I am aware that Ordinary People was based off a book. But the movie adaptation got Robert Redford an Oscar, so that’s what we’re going with here. Fun fact, this film was actually shot at my mother’s high school in Lake Forrest, Illinois. One of her friends was this close to Timothy Hutton (squee?). Another story with surprisingly dark, but redeemingly thought-provoking, themes, Ordinary People revolves around family identity more so than school. The look it inspires is pretty much textbook early 80’s. We’ve got a classic wool sweater and brown boots this time. The heels on the boot might attempt to modernize the look, but if we’re being honest, it’s charm lies in its dated-ness. And it is pretty charming, in my opinion. Oh and the books are an official accessory here.

No. 3: Blair Waldorfplaid skirt, black heels, bow blouse, pearls, LOFT

There’s a lot to love, a lot to hate, and a lot to roll your eyes at when it comes to Gossip Girl’s resident “prep”. Note the quotations. Her fashion sense is something I can generally (GENERALLY) stand behind, though. In my mind’s eye, this is Blair’s outfit when she’s slipped into her imperturbable “I’ve not time for men or friends or feelings, just ruling the Upper East Side” mindset. This is your running a company (as opposed to plotting a high-school takeover or visiting your psychiatrist, see above, respectively) look. Pearls and a bow blouse soften the heels and feminize the plaid, but it’s still a powerful look. Wear to business meetings, or to tea with a Duke–as one does.

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