Michael McClung

Retired Nautica fashion executive Michael McClung doesn’t wear socks and never did, not even at corporate meetings. One of the style maverick’s favorite Manhattan summer looks was Bermuda shorts, button-down shirt and blue blazer. Recently he bought a pair of shoes even though his wife informed him they were slippers. "They’re soft and well made," he declared. "I’m wearing them." Soon a fashion spread in Esquire showed those same slippers with a tuxedo. "I don’t care about dressing as part of a tribe," he says. "But I do look for comfort, and I like color." He leans toward Zanella slacks, Zenga shirts and Ferragamo shoes. He has a closet full of cashmere and recently purchased a dozen suede shirts in shades from mango to eggplant. "I wear them as jackets." The 52-year-old pilot, sailor, tennis player and golfer now sells real estate for Michael Saunders. And his favorite shoes since moving to Sarasota? Flip-flops, of course. Vest and sweater by Marina Yachting, pants and shirt by Arnold Zinberg.

Chad Glauser

The 30-year-old general manager of Glauser Mercedes-Benz admires beautifully designed, high-performance cars. He feels the same about his wardrobe. The New Jersey native defines good clothes as functional art and will consider anything from cotton to cashmere as long as it’s well made and exquisitely tailored. He favors dark Armani suits for the workday and shoes from John Lobb, a favorite New York boutique.

"For business I want to feel confident and present myself well so I choose quality labels and classic, refined looks. But at home relaxing with friends or my girlfriend, Lisa, it’s strictly jeans, sneakers, a T-shirt and a baseball cap." Glauser buys in abundance, locally and while on vacation, and recycles frequently, giving clothes to pals and office staff. One thing he won’t recycle: a Burberry shirt Lisa bought him for their first trip together. "It not only looks great, but seeing it brings back good memories." Clothes by Armani Collezioni.

Hank Battie was nine when he bought a sweater at Webb’s on Palm Avenue with earnings from yard work. "I chose a sweater," he remembers. "I was impressed by Johnny Mathis, not his voice but his vast collection of handsome sweaters." Over the years Battie’s regard for the power and pleasure of quality clothing intensified ("We really dressed at Sarasota High in those days"), and today the 58-year-old style guru owns 13-year-old Cravats’ Custom Clothier for Men in the Sarasota Quay. "Whether you’re in New York or a small town such as ours, only about 10 percent of men will be well dressed with individual style," he says. "The trick is to wear what flatters your body type, invest in quality and insist on careful tailoring." Classics in his closet? "I always own two navy blazers with interesting gold buttons, not shiny. One is single-breasted, the other is double. A quality blazer is a true friend." Suit by Canali, shirt by Hugo Boss and tie by Zegna.

Philip Mancini

The 42-year-old co-proprietor of Michael’s On East favors black clothes, gold jewelry, fast cars and cool music. For work, the king of caterers opts for black Kenneth Cole pants, dark shirt and Kenneth Cole rubber-soled shoes. Although he likes to shop (especially in Las Vegas, Boston and Providence), his greatest passion is music. "I own over 1,000 CDs and I play the radio at night to fall asleep. And I’m at every concert that comes this way." Mancini scours his closets regularly, giving clothes away to friends. Lately, he shops the Internet, buying six pairs of the same-style slacks and a dozen shirts at a time. He never buys just one pair of shoes. "I know what makes me feel good, so why mess around?" he says. But with jewelry, it’s different. "Most of the fine jewelry counters know me," he admits. "I buy for myself and I love to select jewelry for my wife, Kim." Clothes by Armani.

Carl Weinrich

When Carl Weinrich, 58-year-old CEO of the Sarasota Family YMCA, was a kid, his parents owned a furniture store, and his decorator mother "used to drag me along when she was consulting on drapes." As a result, expertise about textiles and colors became second nature. The rare male who enjoys recreational shopping, he even orchestrates shopping expeditions for his wife, Cindy.

A few years ago, when Cindy bought a show-stopping red designer gown for the YMCA’s Going For The Gold gala, Carl got busy scouting a coordinating outfit. In a Cuban men’s store in Miami he found a flamboyant red tux shirt with a dramatic black ruffle and added red and black socks. People still remember seeing the couple make their entrance. Who knew the man who has made Sarasota’s Y a national leader in foster care, family services and cutting-edge facilities is also at home on fashion’s fast track? Sweater by Jhane Barnes, pants by Armani Collezioni.

Pedro Reis

His years of training as a professional aerialist show in his bearing, and Pedro Reis, the 44-year-old director and co-founder of Circus Sarasota, knows how to claim a spotlight. Whether he’s wearing the ringmaster’s red coat or a tuxedo, he radiates razzle-dazzle and sex appeal. "When I’m meeting donors, I stick to conservative business attire," says Reis. "I favor a body-hugging European cut, and I know how a garment should fit from years of wearing costumes." He looks for items that "catch my eye right away" and admits that "as a practical person, I love a sale." Because of a long-ago accident, he insists on comfortable rubber-soled shoes. Any treasured pieces? "A clown-pattern necktie from my days in circus school in South Africa. I wear it often and will keep it forever. It’s a link to my past." Vest by McNight Tiem, tuxedo by Armani.

Ray Sandhagen

Banker yes, boring never. SunTrust Bank Southwest president and CEO Ray Sandhagen learned the value of a conservative dark suit as a young trainee. He adds pizzazz with colorful and zany neckties. His closet boasts at least 60, and he recycles twice a year, delivering them to local charity thrift stores. For casual Fridays, he sticks to slacks, golf shirt and sports jacket; and for relaxing at home it’s usually a Tommy Bahama shirt, Polo shorts and Topsiders. To save time getting dressed, the 53-year-old Sandhagen organizes his closet by color and degree of formality. "Spend money on alterations," he advises younger professionals. "A sloppy fit symbolizes an uncaring attitude." His suit choice is most often Brooks Brothers. Since his social life is full, the banker keeps three tuxedos in his closet and rotates them. He favors a single-breasted, vented style and, of course, has fun with flashy bow ties. Suit by Canali and tie by Brioni.

Tom Luzier

A passionate preservationist and advocate for the arts, 36-year-old attorney Tom Luzier grew up and still lives in a 1925 bungalow built by his grandparents. He calls girlfriend Renee Phinney his "fashion barometer," who spurs him to be creative, including with "goofy ties" and trendy Burberry plaid shirts. At the Mistletoe Ball, he once showed up tieless and rakishly undid the top two buttons of his shirt. He wore a tux jacket over black silk pajamas to the UnGala Gala. Strictly Brooks Brothers conservative in the office, he’s a stickler for fit. "I used to be skinny; now, let’s just say I’m complacent, but I hate that baggy look." And deep in his closet lurks a madras shirt he bought for $65 of his own money in high school. "It doesn’t fit any more. But what can I say? I’m a preservationist." Shirt by Jhane Barnes, pants by Armani Collezioni, shoes by Ferragamo and watch by Armani Emporio.

Aaron Degroft

As head of the team that restored the Ringling Museum’s Cà d’Zan, Aaron DeGroft understands fabrics, design and style. And he notes that John Ringling (subject of DeGroft’s Ph.D. dissertation and upcoming book) could be a fashion mentor today. "He was an elegant dresser," says DeGroft. "He had his shoes specially made for his long, narrow feet. He had a favorite crossword-puzzle necktie and often went out with a cane. You’d notice him on the street." DeGroft, who played baseball at William and Mary College, has an athlete’s small waist and must have his jackets altered to fit properly. His favorite look is a herringbone jacket, camel pants, royal blue shirt and a bright necktie. The 37-year-old is partial to Italian suits and Cole Haan shoes and collects watches. Any falls from couture? "My old college T-shirts emblazoned with ironic sayings. Some are threadbare, but I’ll never get rid of them." Tuxedo by Armani, tie by Brioni.

Mark Famiglio

Jet-setting entrepreneur and philanthropist Mark Famiglio (pictured here in Key West) owns a wardrobe that fits a myriad of occasions and includes seven tuxedos (mostly Armani) and four white dinner jackets. Relaxed black attire is for Sarasota Film Festival parties he hosts for Hollywood luminaries. A man who loves the art of the deal and will fly anywhere to close one, 44-year-old Famiglio often lives out of a suitcase aboard his private plane. In the past his closet was arranged to accommodate his fluctuating weight, which escalated out of control after a motorcycle accident in 1997 left him in a cast and wheelchair bound for months. Now he’s 80 pounds lighter, and his new favorite piece of clothing is a pair of paint–splattered blue jeans that he wore 20 years ago. Jacket by Fres for SFA, shirt by Zegna and Armani Emporio watch