I come from a blue-collar family. My father worked at the American Can Company as a mechanic. He broke his back and was disabled, and the first memory I have of him is in the hospital. My mother was a working mother — she had two jobs. Everybody in the house had to help out. I was the first in my family to go to college and so, growing up, I thought that dressing well opened doors.

And did it?

For me it did. I’ve always loved fashion and I started working at [the Boston haberdashery] Louis Boston when I was 16. Later I went into the management training program and began to learn the business there. Already in high school, though, I’d been voted best-dressed, so the interest was always there. One irony is that, in my yearbook photo, I’m wearing a fawn-colored corduroy jacket with a black turtleneck — and I’m still wearing a black turtleneck now.

Is it accurate to say your approach to design is that of a traditionalist who is fashion-forward, though not so much as to scare off consumers?

When I got into the business, there was a very preppy point of view: saddle shoes and pink button-down shirts. There wasn’t a sophisticated American option. My goal was always to dress American men and make them feel better. Of course, at the time you had Armani, with the softer form of silhouette. Armani was a big thing in my world. He defined the ’80s and the ’90s. He was the standard-bearer. But on Wall Street at the time, if you wore Armani to work, they’d say, “Go home and take off your pajamas.”

So you found an opening between what Armani and others were doing and the man in the gray flannel suit?

You have to know your place in the universe. Preppy hung on so long, and I felt it tended to make American men look provincial. I thought, what can I add? How can I make a suit a little more fluid, sexier, less schoolboy? How can I get the natural-shoulder Ivy League guy to move a little bit? I found my white space there. I was one of the few designers who were anchored in tailoring. So if Armani was Europe, and Ralph Lauren was the United States, I was in the middle of the Atlantic.