When I was in my mid-20s, a struggling writer with a handful of part-time jobs, I got a poorly paid gig as a film extra. My scene was in a hip bar. On set, I sat down to have my hair done. The stylist mussed it around a bit and then pulled it into a high ponytail. She stuck a bunch of bobby pins into my head so hard that I thought she was trying to stimulate specific areas of my brain. Then she frowned at my head in the mirror.

“No,” she said. She extracted the pins, brushed out the ponytail and then tried some teasing. She added a sassy braid along one side and then unbraided it. She called over a fellow stylist. And then another.

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“I just can’t,” she said. She pushed my head around a bit, a subconscious kind of movement, like an irritated receptionist drumming her fingers. “I can’t make her look cool.” No matter what she did, I looked as clean-cut as an Archie-comic character.

The other stylists nodded sympathetically. It was, indeed, a problem. Finally, someone put a leopard-print hat on my head, Blossom-style. “There,” said the stylist, with a sort of determined cheer. “Much better.” We eyeballed each other in the mirror, both fully aware that this was not much better.

We’ve all coveted a look that we felt we couldn’t pull off, whether it’s preppy, boho or my lukewarm attempt at edgy cool. But why do we take it for granted that some styles are out of our reach?

Often it’s because we accept the common wisdom that factors like our body and hair type, and even our face, dictate our sartorial options. Could Reese Witherspoon be believably made up like a badass? Sofía Vergara as a nun? If you’re more patrician Gwyneth than punky Lorde, you might assume that dabbling in black mesh and chokers will make you look silly; if you’re a tomboy type, you might feel like eveningwear never looks quite right on you.

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Why women don’t often experiment with their style on the next page…

Then there’s the fact that we’re often more interested in hiding trouble spots than experimenting with the looks we really love. Too long-waisted, too busty, too short—by the time we’re in high school, we’re already intimately acquainted with what the world deems wrong with us. Not looking clueless becomes more important than feeling fabulous: In a world of unlimited fashion options, we learn to play it safe. I know I did.

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In high school, my best friend and I would walk the halls like a pair of mismatched bookends: She was in 14-hole Dr Martens and ripped T-shirts featuring Paul Simonon smashing his guitar; I looked like my family owned stock in Gap. Secretly, I would have loved to try her look, but even as a teen with a nascent sense of style (and self), I was already too shy to take a sartorial leap. I figured my girl-next-door looks would suck the cool out of any punky threads.

Of course, a wider variety of styles will come more easily to some women than others, and a new look will always give you a bit of a jolt when you first look in the mirror, like the first time we saw Felicity’s shorn locks. But sometimes taking the plunge is all it takes—having the fortitude of style-centric imagination.

Before I saw Kill Bill, I wouldn’t have believed Uma Thurman could pull off a Bruce Lee jumpsuit, but damn if she didn’t wear it like she was born in it. And who would have looked at clean-cut cutie-pie Bettie Page and realized she could not only pull off sexy fetish gear but would become an icon for it?

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Can the writer pull off a punky goth look? Read on to find out!

Recently, my friend threw a party in a goth club not far from my apartment. I combed through my wardrobe, feeling lost about what to wear and wishing that my high-school friend still lived nearby. I couldn’t help but think wryly of the film-set stylist: If I couldn’t muster hipster, what chance did I have of pulling off goth?

But fast-forward to halfway through the night: I’m on the dance floor, sweaty hair sticking to my neck, music blaring in my ears. I’m in motorcycle boots, a studded sleeveless top and a black mini-skirt, with vampy lipstick and seriously smoky eyes—worlds away from my usual evening look. A fellow dancer shouts over the music, “You look amazing!”

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And I felt amazing. Sometimes there’s a fine line between costume and armour. A new look can feel awkward, even silly. But if you give yourself over, sometimes it can feel more like a vacation in the superhero version of yourself—a chance to let your sexier, more mysterious or edgier self step out.

Fashion, after all, is aspirational, and it’s a long life to stick to sensible pumps

A moment, please, for Olivia Pope
Now there’s a woman who wears her clothes with conviction. Lyn Paolo, costume de- signer for Scandal, on dressing a character who has become a fashion phenomenon, spawning breathless Pinterest boards and sellout runs on designer and look-alike fashions: “When I’m designing a more fashion-oriented show, I have to look at the actor and the character together,” explains Paolo.

“Body type always speaks to the character, but it’s my job, and the job of hair and makeup, to transform an actor into the character. I always feel that when an actor looks in the mirror and says ‘that’s her!’ I’ve done it.”

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