New Yorkers On the Clothes That Mean the Most to Them

Racked is no longer publishing. Thank you to everyone who read our work over the years. The archives will remain available here; for new stories, head over to Vox.com, where our staff is covering consumer culture for The Goods by Vox. You can also see what we’re up to by signing up here.

This is an excerpt from Worn in New York: 68 Sartorial Memoirs of the City, a collection of clothing-inspired stories from all sorts of New Yorkers, as told to Emily Spivack. The book is available now from Abrams Image.

---

Deborah Berke is the founder of the New York–based architecture firm Deborah Berke Partners and is the dean of the Yale School of Architecture. She was born in Queens and lives in Manhattan and New Haven, Connecticut.

When it rains in New York, it’s horrible, period. It’s as though people have never seen rain before and they don’t quite know what to do. You have to look up to make sure no one hits you with an umbrella. You have to look down to make sure you don’t step off the curb into a two-inch-deep puddle. It’s just... an assault. It rains everywhere, what’s the big deal? But rain in New York is a particular insult. I’m saying this as a lifelong, multigenerational New Yorker. It’s worse than snow.

I wear a hat when it rains rather than carry an umbrella. I’ve had this one from Worth & Worth for more than 25 years. I know because I bought it right before I got married and this year we celebrated our 25th wedding anniversary.

My husband, Peter, and I grew up in the same neighborhood in Queens. We met when I was 10 years old. We were friends for 27 years — pen pals, actually — before we got married. I went to RISD to study architecture. I knew cool people. I hung out downtown. All my boyfriends were starving poets. Peter was pre-med, a total straight arrow, an athlete. We were buddies. I knew all his girlfriends and he knew all my boyfriends. One year, though, when we were well into our 30s, he wasn’t dating anyone and I wasn’t dating anyone. We went out for Chinese food, which we would have done even when we were with other people — as I’ve-known-you-forever friends. That night, though, he asked if I’d like to go back to his apartment, and I thought, “If I sleep with this guy, I’m either going to marry him or it’ll be the end of our 27-year friendship.” Six months later we were married.

A few months before we got married, I wore this hat out one night with Peter. At the time, I had an Annie Hall look — thrift store vests over old cashmere sweaters with jeans, work boots, and, you know, my hat. The night was stormy and the hat blew off my head into the middle of the street. A taxicab drove over it. It didn’t quite have tire marks on it like in the cartoons, but it got crushed in the pouring rain. Peter ran out into the middle of the street and got the crumpled, rain-soaked, slightly oily hat. It was a chivalrous move. We took it to the hat doctor on lower Fifth Avenue together. It was early in our romantic relationship but well into our almost three-decades-long friendship. It felt like a project, like buying a couch or getting a dog — everything was great because we were doing it for the first time together. They cleaned it, steamed it, and reshaped it.

I treat the hat rudely and inappropriately, but I’ll never lose it. It doesn’t live in a hatbox; it just sits on a shelf in my closet. On a day that’s cloudy in the morning and forecast to rain later in the afternoon, I kind of fold it in half and smoosh it into my bag. When it rains, I pull it down over my head to make it look like a bowler, even though it’s not meant to be worn that way. And then it gets rained on and takes on that nasty smell of wet wool.

The fact that this hat had this traumatic experience, almost like a living thing — my not-yet-husband running out into the middle of the street to rescue it, us taking it to hat rehab — makes it a meaningful part of my life. I may treat it poorly, but I’ll never forget it.

When I was younger, the hat looked cool, but now I look ridiculous pulling it down over my head to give it shape. Peter still loves it. He thinks I look cute in it. I try to look like a creative elegant person in my mostly black clothing and tailored look. And then I put this damn hat on because it does the job.

---

Jenna Lyons was the president and executive creative director of J.Crew. She has lived in New York since 1987.

In 2011, something incredible happened: I was invited to the Met Ball. It felt frivolous and self-obsessed to think too much about what to wear, so at the last possible moment, I decided I should deal with it. Hanging in the hallway outside of my office was a wedding dress sample we’d never wound up making. I thought, “I can turn this into a skirt.”

I had a men’s cashmere sweater in my office that I’d wear when I was cold. I threw that on over the skirt and that became what I wore. Wearing a men’s oversize sweater was the antithesis of the Met Ball.

The Met Ball red carpet consists of about 80 steps up to the entrance. When I arrived, I walked the red carpet to the top of those stairs. I looked back and saw that the skirt had lost hundreds of feathers. A sea of feathers was floating down the steps in my wake. Some poor guy was running out onto the red carpet trying to pick them up, because Beyoncé was coming up the red carpet next and no one wanted feathers from my skirt in Beyoncé’s pictures.

The energy inside was so intense. It was exciting. It wasn’t like watching from the sidelines. I was standing next to people who I had seen only in magazines and on TV. There was American royalty in the room. I learned quickly that all the cool kids were hanging out in the bathroom — that’s where the party was. Girls were helping each other get their skirts over their heads to go to the bathroom because people were wearing massive dresses, crinolines, and corsets. The boys would come in and be rowdy. People were sitting on the counter. No one could get to the sink. Everyone was smoking cigarettes, smoking around all these flammable dresses, not to mention priceless art. They’ve since cracked down and there’s a guard in the bathroom now, but that year, the bathroom was the most insane situation.

This feather skirt left a trail wherever I went that night. After we left The Met, we drove to the party that Valentino hosts every year. I left feathers in the car. I left feathers at that party. Then we went downtown to a place called Up and Down. Someone met me later who had been at the same after-party, and they had a cup of feathers from my skirt in their hands. I ended up at the Boom Boom Room until well into the early hours. I sat in the corner like I was nesting and left more feathers behind. I liked that I was leaving pieces of myself everywhere, that my skirt was disintegrating all night.

I felt like a goose in this skirt. But it was also the first time I really felt glamorous. It’s so delicate and soft, yet it’s vast. It’s this massive undulating skirt. Trust me, you can’t hide when you’re wearing it.

---

Billy Gonzalez is the owner of Billy’s Deli in the Bronx. He grew up in the Dominican Republic and has lived in New York since 1983.

Like most immigrants, I came to the United States because my mom wanted to have a better life. I arrived in New York from the Dominican Republic in the winter of 1983 when I was 16. It was cold and ugly. I wanted to go back the same day I arrived. I told my mom, “My dream is not here. How am I going to play baseball?” Since I was a little kid, my passion was to be a baseball player. But I stayed because I wanted to make my mom happy.

I tried out for the Yankees and the Mets in 1986. I never got signed, because I’d broken my leg. I had been hit by a car a year earlier and my whole life had changed. I had good power, good hitting, I had almost everything, but the main reason they didn’t sign me was because of my leg.

This uniform is from the last time I played baseball 20 years ago, when I was playing in the Crotona Park league in the Bronx, the best minor league in New York City. We played two to three games per week each summer. I played third base. I was playing with my heart, but my leg never entirely healed. Every baseball player knows when their body isn’t working the same way, when they’re not seeing the ball the same way — they know when they need to retire. I knew it was time to go.

I decided to run my own business. I started my deli with $100 in 1998. The guy who had the deli before me was probably very tired. He told me to pay him $100/week for five years to take it over. I gave him what I had in my pocket and I got the business. This is my passion now. I love this business like I loved baseball before. I work almost every single day, 12 hours a day. As soon as I arrive in the morning, the only thing I think about is the business.

Every penny I made, I put back into the floors, the ceiling, the walls, the equipment, redoing it little by little. I had this crazy guy paint the night sky with a coyote on the ceiling. The nighttime is so beautiful when there are a lot of stars and this glow from the sky. I wanted everybody coming into my store to look at the sky.

I work here with my wife. She works in the kitchen and I run the front. She was originally a customer. She liked my sandwiches. She was on vacation from the Dominican Republic and she came to the store and ordered a chicken sandwich. She came back for another one the next day and I decided to give her my number. I told her to call me at 10 p.m. And she did. She returned to her country and we talked on the phone every single day. Then she came back to see me, and we have been together ever since. I had been feeling lonely and depressed because I had gotten divorced and my kids were living with their mother, but I said, “God, please send me a beautiful wife,” and he did.

I’ve been in this neighborhood for 35 years. I see a lot of things, good and bad. Every night at 10 p.m., we give away the food we don’t sell, because we want to keep everything fresh. Usually between 20 and 25 people come by. Sometimes, people will come in and say, “Billy, you might not remember, but I was in that line looking for food and now I’m good.”

One time my son, Jonah, when he was 10 years old, asked, “Daddy, why are these people always in line?” I told him it’s because we give away anything we don’t sell. I told him, “It’s better to give than to receive because every time I give to anybody, I feel good.” Later, my son told me one of the kids at school said that he didn’t have money to buy lunch, and his mind went back to what I said about helping other people. Even though he was hungry, Jonah gave money to the other boy. I told him, “You’ve done the right thing.” That day, I cried — not in front of him — because he had listened to me. I feel lucky. I have my family, my kids are proud of me, and there’s nothing better than that.