Destinations

Fifth Avenue: Through the Eyes of New Yorkers

A panoramic view of the city’s most famous street.

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In celebration of Fifth Avenue — a stretch of New York City that will soon turn 200 years old — we reached out to a few notable New Yorkers and asked for their memories, impressions, and opinions of the legendary street. For visuals, we partnered with 100cameras, a nonprofit that provides photography workshops to kids around the world. With programs in locations from Peru to Iraqi Kurdistan, 100cameras’ mission is to empower youth by teaching them to show how they see the world and their place in it. In this case, we worked with students from their program at City Knoll Middle School on West 53rd Street in Manhattan, just a short walk from Fifth Avenue. The photographs here show the iconic thoroughfare, seen through the fresh eyes of young New Yorkers.

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AS A PERSON who did not grow up in New York City, I spent the early part of my life harboring very weird notions about what the city was actually like. My naive idea of Fifth Avenue was mostly informed by watching shows like “Green Acres” and “Dynasty.” According to the television of the ’70s and early ’80s, Park Avenue was where rich people lived, and Fifth Avenue was where they shopped, had lunch, and occasionally slapped each other while drinking Champagne in the back of speeding limousines. 5th Avenue was also a candy bar that, when first introduced in 1936, was named to associate itself with the most fashionable and fancy part of the city. Fifth Avenue was almost always synonymous with razzle-dazzle, the height of style, high art, and impossible wealth. Now that I’ve spent the better part of three decades in the city, I have a much better understanding of what this particular stretch of New York City has to offer me, even if it remains somewhat charmingly inscrutable.

In 2024, Fifth Avenue — which extends north from Washington Square Park in Greenwich Village all the way up to West 143rd Street in Harlem — will be 200 years old. And while the full expanse of the thoroughfare cuts across a wide swath of famed neighborhoods — Millionaire’s Row (across Central Park between 59th and 96th), the aptly named Museum Mile (from 82nd to 110th, home to the Met and the Guggenheim, among others) — there’s one particular section that remains forever lodged in our cultural psyche. Starting at the corner of 60th and going down to 49th, the “greatest retail strip in the world” is home to some of the most luxurious shopping on planet Earth. That includes iconic New York mainstays like Saks Fifth Avenue, Tiffany & Co., Bergdorf Goodman, Rockefeller Center, and flagship stores for seemingly every luxury brand currently in existence. Depending on whom you ask, this part of Fifth Avenue is either the most glamorous and aspirational part of New York City, a sort of jewel-encrusted architectural fantasia that turns the idea of window shopping into a true spectator sport; or it’s possibly the worst, a shiny manifestation of excess that is all of our worst capitalist desires writ large. In reality, it’s both, which is also what makes it so fascinating.

When I reached out to a few dyed-in-the-wool New Yorkers to give their thoughts on the world’s most famous avenue, I naturally started with Fran Lebowitz. “Did you know our new mayor wants to open a casino on Fifth Avenue? A casino. Can you imagine?” She fumed. (She’s not wrong — there are actually talks afoot to open a glamorous Monaco-style casino atop Saks, of all places.) Fran might be appalled, but I have to admit I sort of can imagine it. A sparkly gambling mecca straight out of “Casino Royale,” while odd, would probably not be the weirdest thing to see on Fifth Avenue these days. It remains the only place I’ve ever taken a casual Sunday stroll where one can be within breathing distance of a million-dollar Cartier necklace and still somehow also be within arm’s reach of a street-vendor pretzel. The always-evolving avenue is also evidence that, if there’s one thing that will remain constant about New York City, it might only be its never-ending capacity to reinvent, redefine, and generally out-glitz itself in ways that no one can ever predict. Fifth Avenue is as New York City as it gets, a glorious mess of beauty, excess, and opulence that is as weird as it is beautiful.


Ira Sachs

Filmmaker

“Fifth Avenue is a long strip down the middle. When you arrive there, you feel the clarity of being at zero; you know east and west, north and south. A parade route, it brings me back to earlier eras of the city, as well as the cultural divides, and the tribal identifications among groups of people wanting power in a city that withholds it. Fifth Avenue is Judy Garland in ‘Easter Parade’ and Frank O’Hara on his lunch break. It’s my grandmother returning to the city she grew up in, still expecting to see women wearing gloves when they walk down the avenue.”


Graydon Carter

Founder and co-editor of Air Mail, former editor of Vanity Fair

“In my own naive Canadian way, I suppose Fifth Avenue represented men in top hats and women in long, shimmery dresses. (Most of my knowledge of New York came from magazines and old movies.) If you’re not in the market for a discount camera or NBA sportswear, it’s pretty much just a useful route to get back downtown.

What are essentially big-box stores in the middle portion of Fifth are bookended on the north and south by fabulous apartments — and in the case of uptown, spectacular views.

I now live on lower Fifth, which I love. It’s still in the Village, but the sidewalks are wider and flatter than in the West Village. And I’m pretty sure that the pot that hangs in the air is of a better grade.”


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Isaac Mizrahi

Designer, author, and performer

“One of the great experiences of New York City is the Fifth Avenue bus. Taking the bus from uptown always felt like a slide down rather than a climb up — the Fifth Avenue bus passes so many fabulous New York City landmarks, it’s like an amusement-park ride for New Yorkers. The museums uptown, like the Met, the Guggenheim, the Jewish Museum, and Cooper Hewitt. Central Park and The Plaza. All the fabulous stores in Midtown, like Bergdorf’s and Saks. Rockefeller Center. Then downtown, The New School, 14th Street, Greenwich Village, all ending at the arch at Washington Square Park, which is, for me, a vortex of great energy in the world.

When I was in high school, I took the Fifth Avenue bus whenever I had the chance, and I adored the feeling of sharing all that with the other New Yorkers on the bus. I dreamt of living in the Village near Fifth. Once I moved here (over 30 years ago), I decided it was the only neighborhood in the city where I could ever possibly live. As my mother says, I will leave, ‘feet first.’”


Thom Browne

Designer

“Fifth Avenue represents what people come to New York for. It’s that ultimate experience of that cosmopolitan city that every young boy and girl from every small town comes to New York to experience.

When I moved to New York in 1988, you had remnants of the stores from the ’50s and ’60s still in their original locations. New York was very different back then too. It’s been polished since.

The style on Fifth Avenue now is totally mixed. Of course, you have the idea of Audrey Hepburn passing by Tiffany’s early in the morning from the movie — that really sophisticated man or woman that is effortless in the way they live, but they live a very privileged life. But nowadays, we live in a much more interesting world, in that things are more beautifully mixed. For the fashion industry, for the world, Bergdorf Goodman on Fifth Avenue is one of those few places that represents fashion, represents quality, represents clothing. At the beginning of my career, I was so fortunate that the merchants at Bergdorf Goodman took a chance on somebody that nobody knew, with a collection that didn’t fit anybody, and no one could afford. They put my clothes in the store’s windows on Fifth Avenue ... I remember seeing my collection in the most important windows in New York, and that was the beginning of it all.

And here we are 20 years later — you get what you ask for.”


Tina Brown

Author and former editor in chief of Tatler, Vanity Fair, and the New Yorker

“I think of the flags rippling in front of the Met and the mass of spring tulips at the dreamy Conservatory Garden across from the Museum of the City of New York.”


Victor Glemaud

Designer

“When I think of Fifth Avenue, I think of New York. I think of power. I think of glamour. I think of beauty. I think of energy. I’ll never forget a year or so before Covid, my aunt was walking on Fifth Avenue and saw a dress of mine in the Saks window on Fifth. And I was like, Wait, what? I hustled over there and was blown away. I was like, Something I’m doing is hitting — we are on Fifth Avenue. It has weight. I miss Bill Cunningham, seeing him lurking and hanging out quite discreetly by Bergdorf Goodman. I think the reason why he was there was because you did see this cross-section of people going to do business in the morning and a different type of person in the afternoon and in the evening.”


Samuel R. Delany

Sci-fi writer

“Every afternoon when I left the Dalton School, I stood at Fifth Avenue and 89th Street, waiting for the number 2 bus to take me back to 110th Street, across to Seventh Avenue, and back up to Harlem. When I started, the Guggenheim Museum was a hole in the ground, and when I graduated in the eighth grade, it was practically finished. When I was a kid, of course, Fifth Avenue was two ways. Now, it just runs downtown.

Back then, the city was cut up into totally nonmixing ghettos. 110th Street was the southern border of the Black ghetto of Harlem, where I lived, up on Seventh Avenue between 132nd and 133rd. Up where we lived, we never even heard about Fifth Avenue, though my grandmother had an apartment whose back windows looked out across it in 1902 into the windows of Harlem Hospital, where, 40 years later, I was born, and two years later, so was my sister. Fifth Avenue divided the east side from the west side, and the division of neighborhoods during my childhood in the ’40s and ’50s was as absolute as if there were a wall. My grandmother’s memories of when the neighborhood used to be full of Germans playing their zithers out in front of their houses when she got home from work (she lived in the first integrated building in the neighborhood) were very hard for me to imagine, though the history of the place actually included tales of Orson Welles and Canada Lee. But that’s to get into Harlem and leave Fifth Avenue behind … ”


Debbie Harry

Musician

“As I approach my 77th birthday, I wonder what I should share about New York City’s fabulous Fifth Avenue. My first experience was walking up and down the avenue as a very small child looking at the holiday window displays. The festivities, the lights, the crowds, and the gigantic Christmas tree at Rockefeller Center at the center of holiday celebrations. What a wonderful time it was!”

Header image: Photography by Melissa/100cameras.

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Our Contributors

T. Cole Rachel Writer

T. Cole Rachel is the deputy editor of Departures. A Brooklyn-based writer, editor, and teacher with over 20 years of experience working in print and digital media, his writing has appeared in the New York Times Magazine, Interview, and the Creative Independent.

100cameras Photographer

100cameras is a nonprofit organization that works with youth around the world and teaches them to process and tell their stories through photography in a way that impacts how they view themselves and their role in their community.

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