How to Be a #GIRLBOSS, as Told by Sophia Amoruso and Amy Astley

Last week, I was lucky enough to attend a Q&A with Sophia Amoruso, founder of the immensely popular online store Nasty Gal and author of the New York Times bestseller “#GIRLBOSS,” as well as Amy Astley, the editor in chief at Teen Vogue and author of the “Teen Vogue Handbook: An Insider’s Guide to Careers in Fashion.”

The Q&A was on the top floor of Union Square’s Barnes & Noble, and even though I got there at least 40 minutes early, the seats were already halfway full (by the time the Q&A was in full swing, they needed to bring extra chairs and also forced some of the crowded standing audience to leave because it was a fire hazard).

I had to buy the #GIRLBOSS book to get a seat, but I was beyond happy to since I’ve heard so many amazing things about it. Flipping through the pages before the Q&A started, I could see why it was an instant bestseller. Amoruso’s blunt, no bulls*** attitude and unapologetic honesty clearly makes this an inspiring text for anyone who picks it up. I can’t wait to read it!

The Q&A started about 15-20 minutes late, but it was well worth the wait. Amoruso comes on stage decked out in a studded leather jacket, graphic tee and a gorgeous sheer black lace skirt with a grey slip underneath. Her new long hair gives her a completely different look from that on the #GIRLBOSS cover, but she is still the epitome of the Nasty Gal girl. Astley follows her up, wearing an all blue ensemble of a silk t-shirt and a vintage patchwork denim midi skirt, which she says she bought off (and it was the last one).

The witty repartee begins, and every single person in the audience is hanging on their every word. The Q&A began with prescreened questions from Astley then moved on to questions that the audience wrote down and put in a bowl up front for Astley to filter through. Amoruso addressed stepping down as CEO of Nasty Gal, a position now filled by Sheree Waterson.

“I didn’t step down, I stepped up,” Amoruso said. She said she missed doing what she loved, touching clothes and going on shoots, which she now gets to do a lot more. Sometimes, she said, her employees are intimidated when she steps on set since she is the “big boss,” but Amoruso simply said “let’s just make cool s*** together.” Her laid-back attitude makes her someone that every person in the audience wanted to work with.

Amoruso also talked about her idea of what it means to be a Girlboss. She remarked that it’s a new thing in which women are choosing the lives they want because now they can, so a Girlboss gets what she wants because she works hard for it. Nothing is handed over on a silver platter, and hard work is essential. This view, which is explicitly stressed in her book, has prompted hundreds of people to send Amoruso letters thanking her for helping get their lives back on track and inspiring them to work hard for what they want.

The most interesting part of the Q&A for me was when Amoruso addressed several paradoxes from her book (which has a new introduction since being released as a paperback). In the new introduction, she says “the older I get the less confident I become.” Amoruso, who everyone believes to be one of the most confident people, said this is about feeling your own mortality and seeing relationships and the things you’ve built and value become ephemeral.

Another paradox was a chapter in her book that says “money looks better in the bank than on your feet.” How could the founder of a website that encourages people to buy trending clothes and accessories tell this to her readers and customers? Amoruso says it’s all about building a wardrobe made up of pieces that are symbols of things that you have done and accomplished. Every piece should be special, and if you think people are going to judge you for not having one of the latest trends, then that’s a great way to filter out the people you should be hanging out with.

Lastly, she talked about the idea of role models. Amoruso isn’t a fan of having a role model, saying it could lead to unhealthy obsession and over-emulation; you end up losing who you are. She says one should spend more time looking at her own life than that of another person. We don’t know how hard it is behind the scenes for another person. No one has a perfect life. Everyone experiences self doubt (and people who don’t, “those people are freaks,” Amoruso says. “Those people run for president,” Astley comments, making the audience laugh).

Astley and Amoruso gave lots of tips for those interested in pursuing a career in the fashion industry. Here are their top 5 tips:

  1. Be entrepreneurial (be original, have your own ideas and be able to think)

  2. Be ambitious, but not entitled

  3. Be eager, but not jumping-out-of-your-chair eagar

  4. Have your own individual style (“Cleavage is cool, but don’t have your boobs way out” - Amoruso)

  5. Social media positions in the industry are on the rise

Amoruso continued to talk about the future of Nasty Gal and the #GIRLBOSS brand. She is currently working on a Girlboss podcast with Slate Magazine, which she said would be just like the witty Q&A (conversations with empowering women and sharing other people’s stories), “but after a drink or two.”

Amoruso pitched the Girlboss Foundation, which gives away $75k in grants to women in creative business endeavors (apply online at!). She brought up Christen Chang of CHRISU scarves, who used the grant to expand her business of gorgeous hand-painted silk scarves, which Amoruso (and me… and Astley) loves for their youthfulness and versatility (you can find them hanging in the windows of the famous boutique Calypso St. Barth). Chang--a self-confessed Sophia Amoruso fangirl--said that applying for the Girlboss grant was “one of the best things I’ve ever done,” and encouraged the audience to “try to define what success means to you and try not to live someone else’s version of success. Being successful is not a final destination, it’s a journey.”

As someone who aspires to work in the fashion industry one day, going to this Q&A was so lovely and inspiring! And as an added bonus, Amoruso liked my photo from the event on Instagram (I had such a fangirl moment). I can’t wait to see where Nasty Gal and #GIRLBOSS go in the future.