Born and raised in Elmira, New York State,
Hilfiger was one of nine children; his father
was a jeweller and his mother a nurse.
Instead of going to a prestigious fashion
school, he started his career flogging second-
hand denim he had picked up in New York
City. Like many self-respecting Americans,
the first items of clothing he bought were
a pair of Levi’s and Converse sneakers. “I was
13 and they didn’t make boys’ sizes. So I
bought the smallest men’s size in Converse
and put tissue in the toes so they would fit,”
he says. “I had to sneak out of the house
because my parents didn’t want me wearing
really, really tight jeans. They thought that
was for, you know, the bad boys. I wanted to
be a rock’n’roll star, but I was tone deaf.”
So dressing like one was the next best
thing, and it was in fact the British rock scene
that inspired him to travel to London in his
twenties. “All of the style was coming from
London with the Beatles, the Stones and Led
Zeppelin. I would absorb all of what was going
on. And it was really so inspirational, because
the look and feel was revolutionary,” he says.
“It was a musical, political and fashion revolu-
tion. It was coming from Carnaby Street. It
was coming from the Kings Road.”
He frequented the iconic Mayfair night-
spot Tramp, alongside the likes of Rod
Stewart and Robert Plant. “On any given
night you would see all the most famous rock
stars in the world — in one place. And you
can only imagine the outfits.”
In 1969 Hilfiger opened People’s Place in
his hometown with two school friends, selling
flared trousers and fringed vests; it was also a
café and hair salon, and a place to smoke joints
and for bands who were passing through to
rehearse — Hilfiger nailed the “concept”
store idea long before they would exist in
modern retail. He expanded from one store
to a chain and later went bankrupt, before
moving to Manhattan and launching his
eponymous label in 1985. In 1992 his company
went public — and Tommy jeans, underwear,
trainers, hoodies and T-shirts went global.
Famously BFFs with Andy Warhol,
Hilfiger made celebrity hobnobbing a serial
profession in the Nineties, first by dressing
hip-hop stars such as TLC and Aaliyah (in
1994 Snoop Dogg wore Tommy Hilfiger on
Saturday Night Live and sales reportedly rose
by $90 million that year) and later Holly-
wood stars. “We really were the first brand
to do streetwear. When the hip-hop kids
started wearing my preppy clothes, they
would buy them four or five sizes too big,” he
says. “I created big logos, which had never
really been seen before. Logos were such a
no-no back in the Eighties — people were
repulsed by them. But I decided to make
mine enormous. And the styles were influ-
enced by sporting teams. The hip-hop kids
started wearing hockey jerseys with big,
baggy jeans and they would drop them down
around their hips, so you could see the logo
on the waistband, with baseball hats back-
wards and boom boxes on their shoulders.”
Fans of the label included Beyoncé, then
an unknown 16-year-old. “We were doing a
fashion show and our DJ cancelled. So my
brother Andy introduced me to this girl
group who offered to do the music for us.
Afterwards I said, ‘Who was the girl in the
middle? Her voice is incredible.’ He said her
name is Beyoncé,” Hilfiger recalls. “Later on
she became the face of our True Star
fragrance. And we became family friends.”
After more than 50 years in the game, it’s
more a case of who Hilfiger doesn’t know. He
was one of the first designers to sponsor
music tours (Britney Spears and Lenny
Kravitz, among others) and invite celebrities
to co-design collections: first was model Gigi
Hadid (“She was not really well known —
her mom was the reality star and Gigi was
sort of in and out of the picture occasionally,
but had a really great personal style”), then
Zendaya and Lewis Hamilton. “Lewis is a
fashionista. He loves fashion. He knows
exactly what he wants, what he likes, what
colours, what fabrics, how it fits, and he has
spent endless hours with the team devel-
oping the Lewis Tommy collection. I love
grand prix racing and we’ve been sponsoring
F1 for over 20 years.”
Indeed, he prides himself on still having
the ability to spot the next big thing, admit-
ting he’s a “student of culture”; he recently
dressed the in-demand young playwright
Jeremy O Harris for the Met Gala. The use of
celebrities to market his label has unasham-
edly been part of Hilfiger’s brand strategy
since the start. “You need a conduit for the
consumer. And you have to speak the
language of the consumer. The consumers
today are very much in touch with the celeb-
rity world.”
Rather than sell a wealthy Hamptons
fantasy, Hilfiger has always sold authenticity.
“We’ve been doing [inclusivity and diver-
sity] since I started People’s Place. That’s
50 years ago. I carried that into my Tommy
Hilfiger business for the past 35 years, and
it’s just a normal way of life for us,” he says.
“But other companies are just waking up to
it. We just think differently. And we’re always
thinking about how we can affect the public
in a positive way.”
This includes overseeing a purposeful
company. Last year, in the wake of the Black
Lives Matter protests, he founded the
People’s Place Program, “set up to mentor
young people of colour, unlock the door
for them within our industry. Giving back
is somewhat self-satisfying, because you
see you’re making a difference in people’s
lives. But also I think if a company is going
Below, from left Tommy Hilfiger outside his first store, People’s Place, which he opened in 1969; with wife Dee, daughters Kathleen and Ally,
granddaughter Harley, son-in-law Steve, daughter Elizabeth and son Richard backstage at the TommyNow autumn/winter 2016 catwalk show
The Sunday Times Style • 29