Rachel Bloom
Credit: George Pimentel/WireImage

I’m shuffling down the hall of my middle school, looking down at my Payless zipper shoes and trying not to lock eyes with anyone who might call me a loser—when I see her. Lagan.

Lagan is the most popular girl in school, and unlike her friends who torture me on a daily basis, she’s so sure of herself, she doesn't need to be mean. Her confidence gives her a beauty that the other girls lack. But right now I’m not noticing Lagan’s inner beauty. I’m noticing her outer beauty, more specifically her style, and more specifically specifically the V-neck under which she’s effortlessly layered a camisole.

Who the f— taught her to do that?!

Ever since then, it’s seemed like people who looked cool had been given some secret password that I didn't know. I’d scour teen magazines and write down every single style tip I came across in the hopes of a breakthrough, yet when I would try the ideas myself, it always looked off. It was like the movie The Polar Express; something was wrong, but I could never figure out what.

After many years I decided to tell myself that I wasn't good at fashion because I wasn't “one of those girls.” I separated women into two categories: those who were shallow and naturally fashionable, and those who were interesting and bad at fashion. Now, when I looked in the mirror, I could say to myself, “Whatever, at least I like to read.”

So since Rebecca Bunch, the main character on my show, Crazy Ex-Girlfriend, is partially based on myself, I insisted that she not be too chic. (You know those TV characters I’m talking about: If you saw them in real life, you’d be like, “How can you possibly afford Dior on a barista’s salary?”)

Rachel Bloom
Credit: Michael Desmond/The CW

However, Rebecca is also based on my co-creator, Aline Brosh McKenna. And unlike me, Aline has always had an innate fashion sense. She even wrote the screenplay for The Devil Wears Prada. That whole Meryl Streep monologue that tracks the origins of cerulean? Aline knows fashion so well that she made that sh— up.

The second Aline and I met, it was apparent that we had different tastes. Aline showed up to the meeting wearing a designer blouse; I showed up in what she remembers to be cargo pants. We recorded the vocals for the pilot’s first song in the bedroom of my longtime collaborator and the show’s producer, Jack Dolgen. I told Aline that this recording session wouldn’t be fancy and that she would literally be sitting on a dude’s bed. She arrived wearing an embroidered blazer and studded leather ankle boots.

After working with Aline for a while, the two categories of women didn't make sense anymore. She was one of the smartest people I’d ever met—and one of the most stylish.

I finally started to get it at a fitting one day when our costume designer, Melina Root, asked me to try on some blazers. “Oh, blazers never look good on me,” I said. But then I put one on anyway. Aline was in the room with me and gasped, “That’s. So. Cute.” I looked around like the homely girl in a teen movie being asked to dance: Me?

No blazer I’d ever tried on before looked like this. It was perfect. Melina explained that she’d picked out petite blazers for me because I have a short waist.

And like that moment in The Usual Suspects when Kujan realizes that Verbal is Keyser Söze, I realized that I’d been focusing on the wrong thing. Instead of trying to make my body look good, I’d been trying to make my body look like other people’s bodies. I wasn't Lagan and would never be Lagan, and that was just fine, because I have a short waist. There are clothes made for people like me. Lots of them! I just needed to find them.

Rachel Bloom
Credit: Scott Everett White/The CW

And if I fell in love with something that wasn't quite right, there was always the option of tailoring, which I used to think was solely reserved for brides, Rockefellers, and Kardashians. Now tailoring has become key to making stuff work with my short waist, tiny shoulders, big boobage, and unflat stomach.

I learned even more about fashion after I got a stylist, Annabelle Harron, for press events. Our relationship deepened the day I tried on an electric blue jumpsuit she had picked out; I know it’s not possible to orgasm from a piece of clothing, but
I swear I was close.

After that I got more confident with clothes, and one day last year I even self-styled. I wore a dress of my own choosing to a benefit for the East West Players in Los Angeles. It had a tropical parrot print and featured a keyhole cutout along the bust. It felt summery, fresh, and purely me, especially with the traditional Hawaiian necklace I wore to honor the person who gave it to me at the event.

The next day I received my first negative fashion write-up. A blog informed me that my look was “Boca Retiree.”

But this time, unlike back in middle school, the criticism didn't haunt me in the same way. I owned my fashion choices. When I looked in the mirror, I felt like everything about my look was right—a far cry from preteen me. Even after that write-up, I still loved that dress. And that was some major progress.

So it turns out my “two categories of women” hypothesis isn’t sound. Because sometimes I’ll wear the perfect electric blue onesie that Annabelle picks out and sometimes I’ll wear the parrot dress. I can choose either—I can be both.

For more stories like this, pick up the August issue of InStyle, available on newsstands and for digital download July 7.