Angel Ramos is getting dressed for work.
Custom-tailored suit, check. Custom shirt, check. Custom tie, check. Vintage cufflinks. Handmade shoes.
No socks, however. Not even custom ones. You got a problem with that?
Ramos, a Miami real estate agent who spends a lot of time contemplating his wardrobe, says that showing a little ankle works just fine among affluent businessmen in the South, and you should believe him.
This month Esquire magazine named him its Best Dressed Real Man of the Year.
For Ramos, 29, who recently joined One Sotheby’s International Realty in Miami Beach, Fla., after several years in real estate in Atlanta, the award is an affirmation of something he knows in his gut: Image may not be everything in his business, but it counts for a lot.
That’s especially true in his specialty, the luxury market, where he’s developing a niche catering to athletes, entertainers and other luxury property buyers and sellers.
"We’re dealing with millionaires, billionaires — very, very high net worth individuals. These boys and girls are putting a lot of thought into what they buy," he said. "If someone sees me in a bar or a restaurant, they look you up and down and they want to see, ‘What’s this guy about?’
"They should be able to say, ‘This guy gets it, he understands what I want,’ " he said.
Barely a week after being awarded the men’s magazine’s annual "best dressed" title, Ramos said he’d been showered with media attention and had heard from clients and friends, though he said it was too soon to know how it would impact his career.
"Everyone asks, ‘Are you going to get into fashion styling now, or are you going into personal shopping? No. Fashion’s cool, but I am a real estate junkie — I am all about business," he said. "I’m still trying to strategically plan how this can make me more business, pick up more listings."
Ramos said he’d heard about the annual contest a couple of years ago, but didn’t enter. His wife urged him to try this year, so he submitted a handful of photographs; about 2,000 other men also entered, he said.
A panel of Esquire editors narrowed the pool to 25 semi-finalists, based on entry photos, a questionnaire, and phone interviews.
Visitors to Esquire.com got to vote on their favorite from the semi-finalists, and that vote-getter became a finalist. The magazine’s editors chose four other finalists (including Ramos) and the eventual winner.
In addition to being featured in the magazine, he has won a $10,000 wardrobe, a $5,000 watch, and tickets to designer shows at the next New York Fashion Week in February, he said.
Ramos said his taste for fine clothing goes way back. As a child in Brooklyn, his mother took him to a tailor to get custom suits for confirmation and church events, he said. He attended New York’s High School of Art & Design, whose alumni include designers Marc Jacobs and Calvin Klein and where developing a personal style was built in to the school’s culture.
"New York is an in-your-face kind of place," he said. "It’s all about fashion in many different genres, whether it’s high-end fashion or preppy fashion.
"Even in terms of hip-hop and rap music, if you walk into Brooklyn and Harlem, they put a lot of thought into what they’re wearing — for their genre, they’re very fashionable."
He’s not always as admiring of some of his fellow real estate agents, however.
"In New York, I was taught, you dress to the nines, all the time, to command respect. You don’t walk into a meeting and look like garbage," he said. "It’s not that a lot of agents don’t take care of themselves, but they don’t put too much care into what they wear and how they look."
When he worked in Atlanta, he said, all too often the daily uniform for male agents was too casual, in his view: golf shirts, golf slacks and boat shoes. Or, getting a little dressier, they’d upgrade to a navy blazer and gray slacks. "Boring," he said.
Ramos estimated he spends $10,000 a year on clothes.
"I get all my suits custom-made," he said. His favorite source is Astor & Black, where suits start at $500, though he usually buys the firm’s three-suit packages (custom-made shirt and tie included), which start at $2,200.
Other labels he admires include Domenico Vacca, Gianni Agnelli, TM Lewin, Eredi Pisano, and Tom Ford.
"But there’s no problem with buying off the rack," he said. "The No. 1 thing that agents should keep in mind is fit, no matter where you shop. The clothes should look like you’re wearing them and they they’re not wearing you.
"Fit is everything," he said. "If a suit is too big or too small, when you’re a real estate agent and walking around sloppy, that reflects on you, it says something about how detail-oriented you are."
He recommends high-end consignment shops for vintage cufflinks or tie bars, but said he’s not inclined toward jewelry, beyond his wedding band and wristwatch.
"I’m a little more classic and old school," he said. "Here and there I wear bracelets that have character — they’re leather or they’re beaded. They have a story."
The no-socks thing is a warm-weather climate phenomenon, he said.
"I don’t go to New York in the winter and not wear socks," he said, laughing. But he maintained that in Miami or other parts of the South — and especially in Italy, where he admires men’s fashion sensibilities — it’s not unusual to see a guy in a fine suit and fine shoes who’s sockless.
"Northerners, Middle-West people, they think it’s extremely weird, and I think it’s something that many people can’t pull off," Ramos said.
"I like to give a little ankle cleavage, as they say in the fashion magazines," he said.
Now that he’s won the "best dressed" mantle, he wonders how far popular expectations are supposed to stretch.
"My wife and I went to a coffee shop in Miami," he said. "We had just finished working out. I had on shorts and sneakers, and she said, ‘What if someone looks at you who reads Esquire or saw your article in the Miami Herald and sees that T-shirt?’
"What am I supposed to do? I go to the gym," he said.
"Now I feel a lot of pressure," Ramos said. "Now, do I have to go get groceries in a suit?"
Mary Umberger is a freelance writer in Chicago.