From working in retail to fashion career - Episode 39

One of the most sought after and exclusive industries is the fashion industry.

Thanks to movies like the Devil Wears Prada and Confessions of a Shopaholic, a whole host of millennials grew up aspiring to work in this space, myself included.

While I ultimately had aspirations of being a magazine editor (which I did go on to do) I was always looking for ways to get my foot into the door in college.

Internships are an obvious way to make connections but are not realistic for everyone.

I have long said that my time spent working in retail at Free People is one of the best things I did for my career in fashion so today I thought I’d get into why I think it ultimately helped me so much and share some of the behind-the-scenes of what working in retail in NYC was really like.

 
 

Create & consume

  • What I’m creating this week: NYFW mini vlog on Instagram recapping the Snow Xue Gao presentation where they invited editors and influencers in attendance to transform into the models, will link

  • What I’m consuming this week: 2 amazing meals upstate in Callicoon: Seminary Hill: venison taretare with hot peppers and straw potatoes and chicken with braised greens and gravy. Black Walnut: charcuterie board and rigatoni with porcini mushroom ragu and grass fed beef

In this episode:

Getting into fashion often means internships, but that’s not always realistic for everyone:

  • Some internships require college credit, which not all students qualify for.

  • Many fashion internships are based in major cities, making access difficult for those who don’t live nearby (though remote work has changed this somewhat).

  • Many internships are unpaid, which isn’t financially feasible for everyone.

I worked at the Free People store in Rockefeller Center from October 2013 to January 2016. I bonded over my love of the brand with a friend at Barnard and we applied to work at the store together. We both ended up getting hired!

Logistics of the job

  • Rotated between different areas of the store: front of the store, back of the store, fitting rooms, register, and greeting customers.

  • Shifts were either 4 or 8 hours and I typically worked two shifts a week, sometimes closing or being on call. 

  • Pay started at around $8 an hour and increased to about $10 an hour after a year.

  • Employee discount: 40% off everything across the URBN group (Free People, Anthropologie, Urban Outfitters, and BHLDN).

  • We were encouraged to dress in the brand’s style but we didn't have to wear Free People 24/7.

  • Overall, it was a friendly and positive work environment!

Working in Rockefeller Center in NYC

Extremely busy, especially during the holidays—on the night of the Rockefeller Christmas Tree Lighting, we had to clear out early.

To keep our jobs we also had to work a few holidays. Black Friday was high-energy with huge sales goals—exhausting but fun. I typically grabbed lunch from the Rock Center concourse, which had tons of food options (RIP Hale and Hearty I miss you every day).

What I learned about fashion from retail

Working in retail actually taught me quite a bit about the fashion industry! Here are some of my top takeaways and transferable skills that I used when I went on to other roles. 

  • Direct customer feedback on what was selling out versus what ended up on clearance.

  • Hands-on styling experience—helping customers find the right fit, color, and styling pieces together.

  • I got to buy great clothes at a discount, which helped me build my personal blog and brand.

  • Free People’s Instagram accounts would sometimes repost me, which was great exposure.

  • Gained deep knowledge of one brand: understanding style categories like Lou (tomboy chic) vs. Candy (super girly).

  • Learned merchandising and store design concepts from the Free People home office in Philly.

  • Noticed trend cycles—some styles returned every season, while others disappeared quickly.

  • Developed people skills, like reading customers to see who wanted help and who preferred to browse.

  • Earned money while doing something I loved and made valuable connections with people who still work in fashion, PR, and retail today.


I'm not the only one who feels this way as I was also able to write an article for Fashionista on how retail jobs influence fashion careers.

Interviewed industry pros about their retail experiences, including Rebecca Ramsey, former fashion director at The Cut, Eric Wilson, fashion editor (InStyle, The New York Times), Lauren Eggertsen, Who What Wear.

Eventually, I put in my notice when I landed my first (and only) paid internship at New York Magazine, which was a big career milestone.

In summary

Working in retail gave me invaluable hands-on experience in fashion, styling, and customer service.

It was a great way to immerse myself in the industry while making money and building connections that still benefit me today.


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The long-form content renaissance - Episode 38