How to Fake Cool

If I can do it, so can you


Yeah, yeah.

Sure, sure.

There was a time, not so long ago, when I argued that you can’t fake cool. And I meant it. Part of me still believes that it is true, but then this other fracture of me says that people change! Ideas change! And with changing ideas come changing energy and when that energy turns into matter, well, we are capable of achieving whatever we set out to accomplish. Right? So recently, I’ve decided to change the narrative: if you want to look cool, then look cool. You can fake whatever you want to fake until, that is, you explicitly make it. (I didn’t write the cliché — I’m just broadcasting it.)

So here we are. Me on this side of the computer screen, you on that side, faking cool as though it is Forever 21-branded leather. But see, here’s the thing that maybe I’m leaving out — in my previous rant (or monograph, if you will), I differentiated cool from effortless, forgetting something of rather significant value about one particular nuance that makes fashion worth participating in: we get to be whoever we want to be without committing long term. By the rules of that notion, fake and effortless, or nerdy and chic, or gothic or girly or whatever all boil down to the same thing.

And that thing, of course, is you.

So maybe this is just another long winded way to say, you do you (without perpetuating narcissism) but in the spirit of “news you can use,” here are also five items that will facilitate your cool a little more seamlessly.

But enough talking, get shopping (or, you know, just looking at the stuff already in your wardrobe with a fresh eye). Here are five things to facilitate your faking cool.

1. A leather jacket, because, duh, Danny Zuko built out that account single-handedly in 1978 when Grease came out. A good version (my favorite is VEDA) is also an easy way not to compromise your summery dresses and girly shit and pridefully nerdy demeanor. It’s like the outfit equivalent of a Michelin star in that once you get one — just one — your life is basically changed.

2. Sunglasses. But not just any sunglasses and not just to be worn indoors. Because fashion is such that trends come in and go out and our perceptions of what looks good is so fickle, right now these sunglasses are round. They might retain a reflective lens though they don’t always. Sometimes they’re two tone. They are not to be confused with the round, wire frames of Coachella fame. Those convey a very different point.

3. A pair of high rise vintage Levi’s. There’s just something about the wash. They’re honest. And you can find them at most vintage shops for under $10. Here’s a guide to make that easier if you’re still not tuned in.

4. Black boots. I am not the best at black boots (unless they come with painted daisies on them) but that is also because I am not the best at being cool. Somehow, this shoe style, in its bleak lack of color, exudes an exclusive energy that makes you want to enroll.

5. A striped t-shirt. Forever the emblem of Serge and Jane — fine, Napoleon’s sailors — there is something so profoundly and inherently French about the shirt that reads, you know, “effortless.” And you know what’s cool? Being effortless. See that cool full circle we just manufactured?


There were lots of stripes in our last episode of Office Apropos. For women who have cool nailed down, check out the differing wardrobes of Maryam Nassir Zadeh, Jane Bishop, and Meredith Kahn. Katie Sturino proves cool isn’t about size, and this kid proves it isn’t about age. Being in a band definitely helps, though. Good news: you’re already in ours.

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