Life as a Runway: What 10 Entrepreneurs Wore to a Girlboss Rally

They came from as far as India and Peru — hairdressers and editors, entrepreneurs and influencers. They came to learn the ways of Sophia Amoruso, the author of “Girlboss” and founder of Nasty Gal, the once-buzzy fashion label that filed for bankruptcy in 2016.

The Girlboss Rally, a physical manifestation of what Ms. Amoruso hopes will be a “LinkedIn for women,” drew approximately 1,000 women to the Knockdown Center in Queens last month. Here’s how 10 of them worked it.

Sophia Amoruso

Age: 34

Occupation: founder, Girlboss

How’s your Girlboss going?

It’s great. We have 1,000 women here. From 31 countries.

What were you thinking when you got dressed today?

Mostly, does this silhouette work? There are a lot of photos and you don’t know what angle they’re being taken from — not that I can dress a double chin. Black can be really severe, but I tried to keep the glam youthful.

Severe, but without being Darth Vader.

Or headmistress. With the hair back it was headmistress. The dress is Max Mara. The boots are Chloé.

Can I ask what the tattoo on your arm says?

It’s a Jenny Holzer quote. It says, “Words tend to be inadequate.” I regret getting a tattoo on my forearm, because people ask to read my arm. And I’m not someone who gets tattoos to show off. It was $80.

Kirsty Godso

Age: 30

Occupation: Nike master trainer

You were leading the room in a workout. How do you dress for that?

Because people are dressed here, I chose to come in non-Lycra. I wore nice pants, from Khaite, but kept a sports bra on, because it’s more authentic to me. I would wear a sports bra under a nice shirt.

Would you really?

This is my casual sports bra. If I’m actually training, I’d wear a different one. This is from Nike Lab, where they do cool, more fashion-style product. You can wear it out. This one I like because it’s more street.

Your shoes have zippers.

These are a Nike Air Force One collab with Acronym, called Lunar Force One. I got these at ComplexCon last year.

Mattie Bradley

Age: 26

Occupation: student

What are you doing here?

I’m trying to become a stylist and break into fashion. It’s my first time in New York.

What did you pack for the trip?

I packed, like, three jackets. I live on the West Coast. I don’t really get to break out my jackets.

Why this suit?

I really needed a nice suit: business wear, but also street style in a way. It’s the velvety crinkle. It’s just different. And not pink, because pink is too common when it comes to femininity.

You matched it all to the sneakers.

I really like the whole chunky, dad-sneaker trend.

Nicoline Roth

Age: 25

Occupation: co-founder, BeBold

Your shoes are from your own company?

We’re producing work wear for women, launching on Women’s Day, March 8th. We’re starting with shoes. We’ve created this special memory foam inside the shoe, so they’re very comfortable.

They’re great. Why did you decide to wear so much pink today?

Generally I like to put together sets. When I buy clothes, I don’t just buy one piece. I buy it for the whole body. This is all from MSGM, in Copenhagen.

It wasn’t to project power, or femininity?

No. In fact, I look like an employee because the girls who work here are wearing pink. Honestly, I just thought it was cool.

Sagal Muse

Age: 24

Occupation: founder, Muse Avenue magazine

What are you doing here?

I’m here to get inspired. I’m also here to get notes for my magazine, so I can inspire other women interested in entrepreneurship.

How did you dress for a Girlboss Rally?

I’m inspired by New York street style, so I went on Pinterest and Instagram and created an ensemble from my inspirations, like Haute Hijab.

Your coat is a big plaid.

I’m really into oversized clothing. It creates dimensions. And plaid is really in this season. Trendy, but not too flashy.

Danielle DuBoise

Age: 32

Occupation: co-founder, Sakara Life

What’s your company?

We’re a wellness company. We deliver tools to people to help them feel like their best selves, in the form of fresh food, snacks, supplements.

Tell me about your pants.

I was inspired today by Katharine Hepburn. She’s an icon, and she’s one of the first women to make pants really sexy. I thought that belonged here.

What about the shirt?

This is vintage Esprit. It was my grandmother’s shirt. Silk. I’m bringing women that inspire me today.

And you’ve got Cleopatra-level jewelry going on: Are those two rams’ heads?

My co-founder is a Capricorn and she has very grounded energy, so I try and wear some of that.

Laura Zheng

Age: 31

Occupation: co-founder, Showbrow

What was your approach to dressing today?

We’re presenting to Uber. I wanted to match my deck, to be honest. It’s black and white. And I brought a backup.

What’s the backup?

It’s silver and sparkly. The opposite.

I love a pajama shirt.

I knew people here today would be wearing plaid blazers, which I love, and they are. This could stand out.

Your necklace is a rainbow.

It’s Gucci. The nails, too. I’m very colorful on the inside. On the outside, I might look like a dark space cowboy, but on the inside I like to keep things bright.

Cory Harris

Age: 55

Occupation: founder, Zip My Dress

People dressed today!

I think that clothing is our armor, in essence. When I was getting dressed today, I was thinking about what would make me feel powerful and confident and comfortable.

I quite like your dress.

This is J. Crew. I love J. Crew because it fits my body type, and also it fits my personality. I’ve got Tory Burch boots on.

They’re strong. As is your cross.

This was my grandmother’s. Her name was June, and she was a tiny redhead white lady who named herself Magdalena and danced Flamenco in Los Angeles. She was ahead of her time: On her days off she wore Converse tennies that she spray painted gold.

I could tell that you’re a boss because of your Rolex.

I’ve worn that thing 25 years. When I was your age, I was dying for one. Buy your Rolex used. Because it’s “used” as soon as you walk out the door anyway.

Jarae Holieway

Age: 25

Occupation: freelance artist

I may be off here, but when I saw your outfit I thought: ’90s music video.

Yes! Very much on point. Today I decided to be ’90s power.

You’re doing shades of blue.

This is a velour jacket. I try to thrift as much as possible. I found this one at a store in L.A. The jumpsuit is a fast-fashion thing. I try to pick things by color, shade and tint.

I can’t even begin with your jewelry. There’s so much of it.

I am an extra kind of girl. When people say, “Take one thing off,” I say, “Put a few more things on.”

Your cap makes me think of old-school NYC cabdrivers.

Yes. It’s leather Adidas. It’s the perfect season to wear it. I would describe my style as fashionable. She looks like she could beat you up, but she also looks like she would be a good time dancing in the club.

Alexandra Apple

Age: 30

Occupation: salon owner and hairstylist

Can we start with your green hair?

I’ve been into green these days. I change my hair all the time because I’m a colorist at my salon in Montreal.

You earrings are very geometric.

They’re from Bing Bang, in New York.

What was your thought process for dressing?

It’s fall, so I like dark colors. I picked up these sweet pants from a Montreal company called Frank and Oak.

Is your engagement ring pink?

It’s a pink sapphire. I had it custom made.