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Photo credit Garance Dore

Hayley Phelan


It’s so cool, and rare, when you read something and you feel like you know the writer. They have presented a story in such a compelling manner you can’t help but relate in some way. This is how I feel about Hayley Phelan. She’s personable with a point of view that leads you to thinking in a new way. With stints at Lucky and Fashionista.com she has joined the ranks of writers who have gone freelance to diversify her work and by doing so regularly sees her byline in Vogue (she’s part of the team covering the Fall 2016 collections for Vogue.com), Yahoo Fashion, Elle, and Interview. She discovered her love of fashion through the freedom her mother gave her at a young age to express herself. When Phelan learned she could turn the passion into a profession during an internship in college, the love affair was solidified.


Did you always know you would be a writer?

Yes and no. I’ve always loved reading and I’ve always loved dreaming up and telling stories. But it didn’t crystallize into a career ambition until I was in college and had my first internship at a magazine. It was sort of a gradual dawning of: Hey, this isn’t just something I love, it’s also something I could get paid for.

Do you have an early fashion memory that led you later to love the fashion lifestyle?

Anyone who has ever met my mother knows exactly where I inherited my interest in fashion from. She has this incredible, innate sense of style–she still introduces me to new labels and trends today, and she’s 64! At the same time, she’s all about practicality and not taking it too seriously–I was really lucky to grow up around that. As soon as we were physically able to dress ourselves, she let us wear whatever we wanted. I still remember one of my favorite outfits from when I was about 5 or 6: striped blue-and-white pants with a ragged hemline that had come as part of a pirate halloween costume, a white t-shirt, and clear suspenders with plastic fish on them that I wore backwards with the X in the front. I wore that for days at a time. Meanwhile, my brother would be in the top half of a Robin costume (from Batman) and shorts. I’m sure we were quite a sight.

With stints at Lucky and Fashionista.com – do you have a preference print vs digital?

I think the medium is becoming less and less important; a good story is a good story whether it lives digitally or in print. Readers today consume media on so many different platforms, there’s really no reason to make a distinction anymore. Behind the scenes, digital is more fast-paced–but print has a lot more moving parts. Essentially, I have no preference–but what I love about freelancing is that I get to dabble in both!

What did you learn at Lucky that impacts your work today?

I learned so much from working with incredible women like Eva Chen, Leigh Belz Ray and Katia Keuthe–editing tricks, visualizing how a story will live 360 degrees, time management. And why Fridays should come with treats.

Ultimately, why do you think the magazine didn’t make it?

It’s difficult to say exactly why. The media landscape has shifted so dramatically since Lucky launched in 2000 that it’s practically unrecognizable. Of course, some titles are going to lose their footing–newsstands are down across the board. I think Condé Nast made a bold move to try to fix Lucky but ultimately it was too late.

In your opinion, what are the most important components to an interesting story?

Simply put: the way it’s told. David Sedaris can turn a trip to the dentist into something memorable and hilarious. It’s all in the tell.

What is click bait for you?

True crime stories. And Wikipedia.

Do you enjoy freelancing? Do you ever miss being part of a team?

Right now, I’m happy freelancing but I do miss being part of a team. Sitting alone all day in my pajamas is so not chic.

Who do you think are the most interesting people currently working in fashion?

Oh, so many! It sounds like a cop out but it’s not: I think the industry is full of such weird, diverse, amazing people, who are constantly creating different things, it’s hard to narrow it down to just a few names.

What do you read on a daily basis?

The New York Times, Elle.com, Racked.com, Jezebel, The New Yorker, Business of Fashion, Fashionista.com, my horoscope.

Where do you like to shop? What sort of items do you invest in?

I really go through phases. Right now, I’m addicted to The RealReal and shopping vintage on Etsy. I check both of those apps almost every day. I am not that much of an investor when it comes to fashion; my uniform every day is jeans and a t-shirt. Though I am lucky enough to have inherited (ahem, stolen) some amazing purses and coats from my mother.

Who would you like to see land at Dior? Lanvin?

I’d love to see Erdem or Simone Rocha at Dior. Stefano Pilati would do great things at Lanvin and I’d love to see him back in the (women’s) spotlight!

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