KING COLE | Kenneth Cole in his New York studio Peter Ash Lee for The Wall Street Journal

ONE THEME PRESENT throughout Kenneth Cole's 30-year career: going against the grain. The footwear and clothing designer made headlines recently for a controversial tweet, his second such contentious message in less than three years. This one seemingly referred to the conflict in Syria in the same breath as shoes. "'Boots on the ground' or not, let's not forget about sandals, pumps and loafers. #Footwear," he wrote.

The tweet was met with outrage—but anyone who knows Mr. Cole is familiar with his penchant for envelope-pushing. "This is a Kenneth Cole Production" (Rizzoli), a new hardcover book released for the 30th anniversary of his company, recaps his history of provocative marketing. An ad from 1989, for instance, showed the fall of the Berlin Wall and read: "Now there's nothing to keep anyone from coming to our Semi-Annual Sale." In a recent interview, Mr. Cole put it this way: "Creating intelligent, thoughtful dialogue on important social issues is what I've done for 30 years."

The book also highlights charitable causes in which Mr. Cole and his wife, Maria Cuomo Cole, are active, particularly amfAR, a foundation that raises money for AIDS research. Mr. Cole, involved with amfAR since 1985, has been its chairman since 2005. He was also an executive producer on "The Battle of amfAR," a documentary that debuts on Dec. 2.

Mr. Cole's do-things-differently approach also applies to how he runs his business. At a time when Michael Kors is enjoying the returns of his rising stock price and Marc Jacobs is focused on an initial public offering for his eponymous brand, Mr. Cole is relishing having taken his company private. The deal, which closed last September and valued the company at about $250 million, freed Mr. Cole of the stresses of quarterly reports, he said, and allowed him to focus on other things, such as international expansion.

The company has store openings planned for India, central South America and Thailand. Mr. Cole believes that sales outside the U.S. can potentially account for as much as half the business. "If a brand is relevant anywhere, it's essentially viable everywhere," he said.

Clockwise, from left: A Robert Longo drawing; Kenneth Cole New York watch; 'The Battle of amfAR'; Domaines Ott rosé; Kenneth Cole New York boots; an antique cobbling tool Robert Longo, "Untitled (Men in the Cities)," 1981, Courtesy of the Artist and Metro Pictures (drawing); F. Martin Ramin/The Wall Street Journal (boots, watch, tool)

My design heroes are: Giorgio Armani and Ralph Lauren, who have both stayed true to who they are for countless years. They've resisted trends and they've continued to deliver a specific, quality product with a consistent point of view.

The one thing a man should have in his wardrobe is: dark denim. You can wear it to work or you can wear it after work.

A perfect day in New York is: getting lost downtown, blending into the streets of the city, and watching people watch people.

The biggest change in the fashion industry is: that today, because of the Internet and social media, it happens everywhere in real time. In the past, fashion began in Paris and Milan, and six months later it came to New York and London, and then three years after that to Omaha and Tuscaloosa.

The high point in my career was: taking the company private. It's totally changed everything about the business. I'd tell you about it, but it's private.

One of my favorite artists is: Robert Longo. I think his work is unique and it expresses a level of energy that I find inspiring.

My last good meal was: at Le Langhe in Milan. I had the veal Milanese. As they say, "When in Rome...."

The accessory I wear every day is: a watch. It's a kind of a security thing for me. And it's easier to look at my wrist to see how things are going than to turn to one of my communication devices.

Sunset in Capri Getty Images

The most beautiful place on earth is: Capri. This summer I went to a film festival in Ischia and we took a boat ride over to Capri. The rock formations are extraordinary.

My favorite TV show is: "The Newsroom." The dialogue is smart and provocative. But I don't watch much TV anymore. And I don't watch anything in real time. I watch it on my own time, which is one of the greatest consequences of technology.

The most stylish woman is one who: has enormous self confidence. If you feel that you look right, it becomes self-fulfilling. You are going to relax. You are going to smile. You are going to own the world that day.

A woman should not wear: a heel that's too high to walk in comfortably. If you can't walk, then you shouldn't wear it.

The perfect scent is: one that doesn't arrive before you and that won't linger when you're gone.

The thing that keeps me going is: caffeine. Sleep is overrated.

I always wear: my own clothes. When I don't, I don't admit it. Life in my shoes has gotten me relatively far. Though it's also gotten me into trouble on occasion.

I collect: antique shoemaker tools. Shoes are by far the most complicated thing to bring to market. It's not just design. You need engineering.

I stay healthy by: making balance the key to everything. I work out with my trainer at 5 a.m. three times per week and I also skip dessert—most of the time.

The best part about the fashion industry is: that it's absolutely interpretive and forever changing. What's fashionable to you may not be to her, and what's fashionable today may not be tomorrow.

My favorite bottle of wine is: Domaines Ott rosé, which we always serve in the summer at our home on Martha's Vineyard. Otherwise, Barbera d'Asti is a great choice.

My must-have tech accessory is: my iPhone 5, because it helps me stay in touch with my most loved accessories—my three daughters.

The piece of fashion advice I would give anybody is: don't choose what you're going to wear because it looks good. Choose what makes you look good.

If I had a free hour, I would: send out more tweets.

—Edited from an interview by Elizabeth Holmes