My Secret Life: Tommy Hilfiger, fashion designer, 59

(Annie Leibovitz)

My parents were ... hard-working and moral. My father was a watch-maker and very strict but also sociable and extremely dapper. My mother was kind and forgiving and would take in all the waifs and strays in our neighbourhood; we always compared her to Mother Teresa. She taught me a lot.

The house/flat I grew up in ... was a modern clapboard house in a small town called Elmira in upstate New York. I'm one of eight siblings, so our five-bedroom house was always a little crowded.

When I was a child I wanted to be ... an American football player. But I was always much too little to be in the team.

If I could change one thing about myself ... I would like to be 20 years younger and a whole lot smarter.

You wouldn't know it but I'm very good at ... skiing.

You wouldn't know it but I'm no good at at ... board games. Sitting still for long periods of time is not something I like.

At night I dream of ... travelling. Last night, I dreamed I was on a motorcycle driving along the highway in Nantucket.

What I see when I look in the mirror ... myself, ageing before my very eyes.

My favourite item of clothing ... has to be my jeans. They are comfortable and versatile: you can wear them anytime, anywhere.

I wish I'd never worn ... high-heeled boots. I thought they looked so good at the time, but have since changed my mind.

I drive/ride ... a Range Rover and Mercedes. I also have a Ferrari Enzo which is a limited-edition model with a camel interior. I wish I had more time to drive it, it's quite a car.

My house is ... in the French Normandy-style, in Connecticut. I also keep an apartment at the Plaza, which I use when I'm in New York City. My most unusual place is on Mustique. It's a beach-front house made entirely of coral; it was based on plans drawn up by the set-designer Oliver Messel.

My favourite building ... is the Plaza in New York. I love living there – all that history, all those interesting stories.

My favourite work of art ... the painting of the American flag by Jasper Johns. I'm also a great Warhol fan and Picasso was amazing.

Movie heaven ... is any Woody Allen film, or 'Midnight Cowboy'; Dustin Hoffman is fantastic.

The last album I bought/downloaded ... was a replacement copy of 'Beggars Banquet' by The Rolling Stones.

My secret crush ... is Grace Kelly, who was endearing and inspirational.

My greatest regret ... was not having gone to business school. I had to learn on the job, which was hard and time-consuming. I opened my first shop in 1969, with 20 pairs of jeans; it was successful at first but then it went bankrupt because of bad decisions.

My real-life villains ... I disapprove of lots of decisions made by George Bush: the war, the meddling in the affairs of other countries, the conversations with dictators; it was a dark time. Obama has given us hope, but he has a huge job ahead.

The person who really makes me laugh ... is either stand-up comic Jimmy Fallon or comedian David Chappelle.

The last time I cried ... was about a year ago, when my baby, Sebastian, was born. I was so full of joy and happiness.

My five-year plan ... is to work less, though I'll never retire. I want more time with my family.

What's the point? I'm not sure, but I know what the point isn't: fighting, war and conflict.

My life in six words ... thankful, appreciative, grateful, happy, hopeful, satisfied.

A life in brief

Born in Elmira, New York, on 24 March 1951, the son of Irish-Catholic parents, Tommy Hilfiger founded his eponymous fashion label in 1984. He sold the company in 2006 for $1.8bn dollars. Hilfiger divides his time between Connecticut, New York, and his house on the Caribbean island of Mustique where he was for many years a neighbour of Princess Margaret. He lives with his second wife, Dee, and their baby Sebastian. This season the designer launches the Icon collection featuring 25 classic American pieces