Heroes of Menswear: Tommy Hilfiger

Tommy Hilfiger, the brand, turns 30 this year — which is more than half the lifetime of its founder and namesake, Tommy Hilfiger, the man. In that time, he’s created a global empire tagged in iconic red, white and blue, propagating a line of preppy all-American staples to runways and showrooms and offices and classrooms around the world. In fact, for a while there in the ’90s, it was almost too omnipresent. But the truth is, he’s still doing good work today — and he’s doing it all without any formal training in fashion design or business. All of which to say: if you care about your clothes, best to listen to what he has to say about them.

It’s All Been Done

“Every successful designer is a re-designer. The pant is already invented. A shirt, a skirt, a sweater, it was already invented. If you look at any fashion brands, there are very few new inventions. There are re-designs, from vintage or the classics, whether we’re talking about a pair of jeans or a gown.”

Fresh Takes

“I grew up wearing preppy clothes, but in my later years I thought they were quite boring. So I decided to redesign all of the classic, preppy clothing from my closet and reinvent a new image and attitude around these clothes. At the time, I made everything relaxed, colourful, oversized, washed, with all sorts of detail and a bit of a sense of humour. Up until that point nothing like that existed. There were button-down shirts and chino pants, but they were normal. I didn’t want normal. I wanted to make them hip and cool and fun and edgy.”

Practice Makes Perfect

“I collect shirts. I have probably every shirt known to man. I’m a bit of a shirt fanatic. I’m always comparing our shirt to everyone else’s and always trying to build a better one. They’re addictive. The fit, the fabric, the color, everything about the shirt is perfect. That’s what I’ve been doing for 30 years — making our shirts perfect. ”

Dress Like A Man

“Men shouldn’t be overly fashion conscious, but I think they should at least be aware of how they present themselves. One thing that bothers me is that a lot of men wear a T-shirt under a suit or a sports jacket, and that’s so ’80s. It makes them look lazy.”