25 Famous Men on How Clothes Make Them Feel

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“I was born into bespoke clothing.” —Gay Talese Photo: BFA, BFA, BFA, Corbis

For this week’s “Men Getting Dressed” series, we asked 25 famous men to talk to us about clothing. What makes them feel masculine? What are they most insecure about? Best are their memories of that first moment of sartorial self-awareness — when, wearing a certain jacket or pair of Jordans, they realized that they looked good and felt great. Read on for Loren Stein’s signature look, Gay Talese’s and Jim Nelson’s childhood suits, and the year when Alec Baldwin’s style peaked.

Lorin Stein, editor
“I wear the same thing almost every day, corduroys and Clarks and a V-neck sweater. Every once in a while I used to try to spruce myself up, always with pretty silly results. It was my friend Rita — who is English, and very stylish — who taught me to stop trying. ‘Those Clarks are hideous,’ she said, ‘but they are you.’ Until then, I’d thought of them as invisible. Rita made me feel like Auden wearing his slippers to the opera. She also sent me to a tailor she trusted — Kirk Miller — so now I have the option of putting on a good suit. I like corduroy or seersucker, depending on the season, since you look as rumpled at breakfast as you’ll look at midnight. The less I have to think about how I look, the happier I am.”

Rodney Smith, photographer
“I wear the exact same clothes I wore in high school. Khaki pants, shirt … Having a uniform of sorts, I find it very comforting and a comfortable response to the world. The ins and outs of everything remain consistent to me.”

Sam Shahid, art director
“If I wear tie-up leather shoes, I walk differently, I talk differently than when I wear sneakers. My mood is different. I think shoes tell a lot about you. They define who you are, what you feel about the day … Your body language changes depending on your shoes.”

Andrew WK, musician
“There is an absence of style, to a degree, in terms of what I wear. I wear white jeans and a white T-shirt and some kind of contemporary supportive athletic shoe. Always a black digital watch, and underwear and socks, too. The main concern is how filthy are the clothes and how offensive is the odor and aroma going to be. Have I taken the clothes off recently? Who am I going to encounter and how will they react? How can I lessen the filth and muck and grime? … That’s my main concern. The livelihood of the people around me.”

Cheyenne Jackson, actor
“I have these boots that I’ve had since I was 15, these steel-toed boots that I got for work at the paper mill. I wore them in my first play … They still fit because you know, my feet are 12-and-a-half and they are always going to be that. So, yeah, I put them on and I feel super butch like a lumberjack.”

Michael Arden, actor
“I feel hella sexy in a hoodie. It sends a message. Not only do I not quite care about how you think I look, I’m prepared for slight drizzle, maybe even a bit of a downpour. Now, that’s hot.”

Austin Stowell, actor
“I don’t wear jeans. I’m not against jeans, I just think there are so many more comfortable options. They’re just, they seem very rugged to me. And, like, I guess because I’m kind of an active guy, I want something that really can help out in that lifestyle, and so I think jeans hinder me more than anything. Chinos, you know? Bathing suit is great. I think if you have a bathing suit on, you have a great day going.”

Ignacio Mattos, chef
“It always goes back to navy, black, and white. That’s when I actually feel the best. I love colors but I don’t think I’m the guy who can pull it off. I feel the best wearing comfortable material. And it always goes back to cotton … Maybe I was 26 when I figured it out: This is it. I need to simplify my life.”

Max Greenfield, actor
“I don’t love ties. I like them. I like the idea of them. Some of them are beautiful but it feels like I’m choking myself and I’m not into it. So, if I could avoid it, I would like to do that. I’ve worn them on talk shows sometimes and I feel like it’s the reason that I can’t speak sometimes. I’m like, ‘Why can’t I speak? Oh, I think it’s the tie around my neck.’”

Wes Bentley, actor
“Shorts are always tough for men. I see some guys pull it off great. I don’t think I could necessarily do that unless I am working out. Maybe then I could, but just wearing them out on the street, I don’t think I could do it and pull it off.”

Jon Michael Hill, actor
“I think I have skinny skinny legs. On my show, Elementary, I wear pretty skinny pants. The designer, she’ll put me in some pretty fitted slacks, but usually the calves aren’t as tight. Like they’re not skinny jeans, so people can’t see how skinny my calves are. I’m pretty self-conscious about that.”

Alec Baldwin, actor
“There was a moment when I thought I looked fantastic. I thought I looked great. For like one day in 1989. I thought I looked so good. I was doing a photo shoot with Greg Gorman. He shot photographs of me for a magazine. And damn I looked great that day, but it’s all been downhill since then.”

Jeffrey Bilhuber, interior designer
“The biggest worry is trying to make sure you can keep people from noticing that it’s all an act. If something comes off as artifice or if it comes off as premeditated, then you have not succeeded. That comes through confidence, that comes from being able to fully understand where you are most comfortable, and what gives you confidence when you put it on.”

Matthew Weiner, Mad Men
“I work with actors who look amazing and are even more insecure than I am. Like everybody else, you want to make sure you don’t look fat — that’s it. Or not that fat.”

Jack Antonoff, musician
“I feel really masculine if I wear a shitty gold chain. I grew up in N.J., and in the early ‘90s a lot of visions of masculinity to me were like men who were not in killer shape with a little gold chain. I’m wearing one right now. And I like that. It’s somewhere between my idea of New Jersey masculine and my idea of super feminine, for me.”

Matthew Patrick Smyth, interior designer
“When I get dressed up in a tuxedo, there’s nothing more masculine than that, just looking proper and confident. It’s almost as if someone takes your shoulders and pulls them back, automatically. You know, whenever someone corrects your posture in gym class, you put the tuxedo on and you stand up straight automatically. It just works.”

Hunt Slonem, artist
“My father was a career naval officer so I grew up with a lot of protocol, uniforms around. So in my life, the closest I’ve come to that feeling of the masculine world is the tuxedo, which I have to wear quite often. It’s not unpleasant at all, it’s very comfortable, very easy — except for putting it on and taking it off. It’s a no-brainer. You feel like you’re a man. There’s no crossover with that. There’s the idea of a uniform, where men and women are defined by what they’re wearing as separate genders. This roots back to my upbringing around a military presence. You can dress it up with studs and cuff links, but they’re basically all the same. It’s easy and it’s very identifiable: You’re a boy and putting on a boy’s suit. Not that women don’t wear them. It’s just a real clear signal of gender, usually.”

Simon Doonan, Barneys ambassador
“Growing up gay in gritty post-war England, I had to develop a thick skin … We had no money when I was young. My sister and I often wore our school uniforms at the weekends. When I was about 10 years old, the album With the Beatles came out. I saw it in a record-shop window and lost my mind. In their black turtlenecks, the lads looked very nouvelle vague. Very beat. I scraped together my pocket money and gave it to my mum. She set off to Marks and Spencer and returned triumphant. The feeling was orgasmic, a transformative magical fashion moment … It was a bridge into a world of creativity and optimism. It was symbolic … I continue to treat clothes that way. I get things that are going to give me that turtleneck kick.”

John Cale, musician
“Gender-free clothing! It challenges any preconceptions of sexuality from both sides of the fence. I’ve never thought of myself as particularly masculine as it’s a misnomer at best. Being a musician and surrounded by art/artists has always reminded me of how unimportant masculinity is at its core. Feeling ‘manly’ happens from the inside … a chemical thing with neurons and such. When I’m in good physical shape and going to the gym regularly — I feel masculine in whatever I’m wearing … especially my new pleated skirt!!”

Patrick Mele, interior designer
“I look at men, of various age ranges, and I think when they look most comfortable, like they haven’t tried that hard, is when they seem to me most masculine, most sexy, most cool … Especially with older men. I look at guys in their 50s or 60s, and that kind of intrinsic style that hasn’t changed, that isn’t informed by trends or isn’t gimmicky, but just kind of oozes out of them.”

Jonathan Adler, decorator
“My bar mitzvah look was on fleek. Navy Brooks Brothers suit, red tie, and mini Gucci loafers — a totally early-’80s power look. There’s a picture of me lounging on a sofa, surrounded by all the girls who were there. I felt powerful and I felt confident. But mostly I felt that I wished they were dudes.”

Jim Nelson, editor, GQ
“I remember being about 9 and wearing a brown thick-waled corduroy suit, looking at myself in the mirror, grooving out on the ‘70s vibe I was putting out, and thinking: ‘Has anyone ever looked more adult? Has anyone ever inhabited the Adult Look more than the man-child standing before you? No, they have not.’ See, this is why the world needs a magazine called Pre-Adolescent GQ.”

A$AP Rocky, musician
“The first time I thought I looked good I was child … From what I can remember, when I really liked something that I wore I was either 6 or 7 years old. I wore the patent-leather Jordan 11s with a black dungaree suit and a white T-shirt. It was Easter and my dad got me those sneakers; they were either white and black or red and black.”

Gay Talese, writer
“I was born into bespoke clothing. My father was a tailor and he had people, distinguished people in the town, in a three-way mirror. And I’d look at my father measuring people, the mayor of the town, the principal of the schools, the editor of the weekly newspaper. And I always thought I want to be measured like that. I felt, you know, clothes can conceal a lot of flaws … You could be a fat man and a good tailor could make you look slender. Not only for women is this true, it’s true for men too.”

Bryshere Y. Grey, actor
“I was in high school. It was dress-down day, I had saved up a little bit of money and purchased me some Louis Vuitton. I wanted to wear it in school. Which I did, and the kids went crazy! I walked through the halls and it was like, ‘Oh, no, he didn’t get the sneakers!’ And I was like, ‘And I got the shirt, too.’ I unzipped the jacket and I had the shirt on. [Laughs] Yeah.”

Reporting by Belle Cushing, Adrienne Gaffney, Kylie Gilbert, Kelly Marino, Jamie Sharpe, Yelena Shuster, and Trupti Rami.

*A version of this article appears in the November 2, 2015 issue of New York Magazine.

25 Famous Men on How Clothes Make Them Feel