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I knew how to use Photoshop from editing photos, but I did not know how to use InDesign, so I designed Nasty Gal’s first website entirely via Photoshop. Also, as I was self-taught, I didn’t know any shortcuts. I moved everything one pixel at a time. I must have spent hours hitting the arrow key, like doo doo doo doo doo doo doo doo doo doo doo doo doo doo doo doo . . . okay, now that box is halfway to where I want it to be, so . . . doo doo doo doo doo doo doo doo . . . You get the picture. When Cody, who helped with the site development, showed me that I could hold down the shift key and move something like ten pixels at a time, it was as if the heavens opened up, the angels sang, and I got back several hours, maybe even days, of my life.

I have always been an observer. When I see music live, I like watching not only the band but the crowd as well. What are their favorite songs? Who’s a fan and who has never even heard this band? Where’s the obligatory fifty-five-year-old man with no rhythm who arrived alone and is louder than anyone else in the room? Currently, I am always trying to imagine things from the customer’s point of view. Now that Nasty Gal’s creative decisions are made by our creative team, they have to look at things from three views: their own, the customer’s, and mine. Thank God I hire brave people, because the inside of my head can be pretty weird sometimes.

Nasty Gal is now at an inflection point where we have to institutionalize the magic, as I like to say. That means that everyone’s job, to some extent, is to pull out of my head what has made Nasty Gal successful for the past seven years. When the brand was an extension of just me, I never had to stop and ask myself whether or not it was “on brand.” Today, our team is constantly working together to examine what has made us successful, what of that we want to keep around, and what newness we can introduce to evolve the brand. We then have to communicate that and share it. Our creative team is learning how to think like I think and I’m learning how to think like they think. Brains everywhere, all the time. Cue air drums.

PORTRAIT OF A #GIRLBOSS:

Leandra Medine, Manrepeller.com and author of Seeking Love, Finding Overalls

When I was a kid I really thought I was going to be a ballerina, but then I realized I suck at dancing. So by the time I was in college, I wanted to become a reporter. I hoped I’d get a fact-checking job at New York magazine out of college, but instead I started Man Repeller.

I was a junior at the time and started the blog because I was writing so much content that was not funny at all and I just felt like I needed a place to inject a little bit of humor. What I wanted to do with my life figured itself out. I did not by any stretch of the imagination think that it was possible to take my blog anywhere that professional stuff happens. Sometimes I still feel like the universe is playing a trick on me. Since 2010, I have since grown Man Repeller from a one-person blog (here’s hoping, fingers crossed) to a website with staff writers and graphic designers and ad sales people and bikini waxers on demand! Just kidding. Fuck waxing.

I remember when I was younger that every time my mom wanted to buy something expensive, she had to run the purchase by my dad. I knew I never wanted to have to ask anyone to appease my indulgences, so that was a point of motivation to work hard. If you’re working, you’re working hard, and if you’re not doing that, what are you doing? I also think you age a lot quicker if you can’t keep yourself busy and under the right, healthy dose of stress. Too much of anything obviously isn’t good, but as my dad always said: Overwhelmingly busy is a much better state to be in than overwhelmingly bored.

Fashion has always informed the way I approach life. It’s also helped me manipulate my moods: I could be having a shitty day but the right pair of shoes can sometimes change that—which is powerful. I make a lot of jokes about fashion, but I love it. And on the topic of style, I think clothing will always look good—no matter how outlandish or ridiculous you might think it is—if you wholeheartedly own it. If you feel equally as excited and comfortable in a fruit-silhouette head contraption as you do in a pair of jeans, the rest of the world will watch. And likely in admiration. There are no apologies necessary for being you.

It sounds incredibly platitudinal, but no one will ever be able to love you if you don’t love yourself. What’s beautiful about it is that if you love yourself enough, you don’t need the validation from anyone else. My advice to #GIRLBOSSes is to get excited about the mistakes you’ll make.

Own Your Style Like You Own Your Used Car

When you don’t dress like everyone else, you don’t have to think like everyone else.

–Iris Apfel

As much as I would like to say that photography was my first love, I think my first real creative effort was getting dressed.

Mom, and me, with her “punked” collar. 1987.

Both my parents were well attired, but my mom especially had great style. Before she headed out the door, she put the finishing touch on her outfit by “punking” (better known as popping) the collar of her ’80s polo shirts. It was always in my blood to care about what I wore and how it fit. At age six, my one true love was a pair of acid-wash jeans with an elastic waist. In sixth grade I became obsessed with the Sanrio crew: Hello Kitty, Pachacco, Kero Kero Keroppi, and the lot. My look could best (or worst?) be described as suburban mall Harajuku girl through a Northern California lens: baby T-shirts, barrettes, and white Walgreens’ knee-high socks that I wore with my Converse One-Star sneakers.

Before I knew that real punks don’t wear polo shirts.

When I was fifteen I liked a pair of bedraggled brown Levi’s corduroys that I found at the Salvation Army by my house so much that I wore them at least five days a week, until they met their untimely demise in a gas station parking lot (I’ll spare you the gory details, but let’s just say that it involved a really upset stomach, lack of a nearby public bathroom, and me crying in shame). Even when I was in my Abercrombie & Fitch phase (yes, even I have succumbed to peer pressure), I washed my jeans after every wear so that they still fit exactly the same as they did when I bought them.

A staple look from my boring-ass Abercrombie phase. 1998.

I was a ’90s teenager, so of course I went through a grunge phase, donning bell-bottom flares that dragged on the ground and an equally shapeless men’s V-neck sweater. My clothing choices were in line with my contrarian nature. As I mentioned earlier, my mom begged and pleaded with me to buy clothes at the mall, a typical teenage girl’s dream; we spent hours there only to leave empty-handed as store after store failed to usurp my preference for the corduroy and threadbare T-shirts I could only find at the local thrift store.

After that, I went through a couple of different iterations of skater girclass="underline" the cute type, with tiny board shorts, a tight tank top, and skate shoes; and the not-so-cute type, when I cut off all my hair and paired those skate shoes with baggy Dickie’s work pants.

At age seventeen I was a crust punk who refused to change her all-black clothes. At eighteen I was goth, which still involved all-black clothes, but at least now I changed them. That was when I lived in Seattle—and the goth suited the gloom. After that, when I moved back to San Francisco, I became a rock ’n’ roller and that stuck for a long time. I hooked my thumbs through my belt loops and did honky-tonk scoots across dance floors. My long hair parted in the middle and I wore exclusively vintage T-shirts with high-waist jeans that practically grazed my boobs.