Designer Tommy Hilfiger shares what it feels like to be in the fashion industry after 25 years and some of the items that are part of his iconic collection.

1. Celebrating your 25th anniversary this year, can you share some things that have changed since you started your career in fashion?

So much has changed. I began my career selling jeans in high school out of the back of my car in upstate New York. I started out with $150 and 20 pairs of jeans. Now we’re a global brand with approximately 1,000 stores in over 65 countries. It is thrilling to see people all over the world wearing our designs.

2. And what hasn’t changed?

My design philosophy hasn’t changed. I have always been passionate about bringing my own twists to the great classics of style. I am endlessly inspired by my consumer and pop culture as well as fashion, art, music and entertainment. We still try to keep it fun, fresh, modern and relevant-this is really important.

3. Can you tell us about the 25th Anniversary collection?

We’ve chosen the 25 essential, iconic pieces in the history of sportswear and given them the “Tommy Twist”. The Icon collection includes 25 timeless pieces-from trench coats to white blouses to a great pair of jeans-that everyone can wear and love forever.

4. How do these pieces relate specifically to Tommy Hilfiger the brand?

Each piece is an icon of great American style. My favorite style icons, such as Steve McQueen, Grace Kelly, James Dean, Iggy Pop, Clark Gable, Debbie Harry and Farrah Fawcett inspired the pieces. These are legendary icons of incomparable, unclassifiable allure and charisma. They each made a permanent mark in music, film, or culture in general. They really personify Classic American style for me.

5. Tell us about the 25th anniversary global campaign, featuring style icons like Steve McQueen and Grace Kelly. Who are these iconic faces and what do they mean to you?

We’re celebrating 25 years of the brand by honoring the faces and iconic personalities that have meant so much to us over years. James Dean, Clark Gable, Farrah Fawcett, Debbie Harry, Iggy Pop. Every so often someone bursts onto the scene by force of sheer charisma. Talent, intelligence, looks, style and individuality come together in a powerful combination and this allure is eternally compelling: one person can have a tremendous influence on culture by just being exactly who they are. It is endlessly inspiring to me as a designer.

6. How do you reinvent a classic?

There’s really no formula. That’s the fun of it. All I can tell you is that it’s always possible to put a fresh spin on a timeless piece, to give it the energy of the here and now, to make it feel really unique. This is my challenge every day, and I love it.

7. What is the most valuable lesson learned from 25 years in the fashion world?

Over the years I have learned to stay true to myself and to be fearless about following my dreams. I’ll never forget when I first saw my name on the billboard in Times Square alongside Ralph Lauren, Perry Ellis and Calvin Klein. It was a crazy thing for an unknown designer to do, but I believed in my vision and it was one of the most defining moments of my life and career. The buzz and controversy surrounding the advertisement instantly put me on the map.

8. Can you tell us about your passion for American pop culture?

In America there is always a dreamer creating some crazy, wonderful thing or dreaming up some revolutionary idea that changes the world. I find it so inspiring. George Lois, the legendary art director, and I worked on a book called Iconic America. We selected iconic moments, faces and symbols of America throughout history-in fashion, art, music, politics, culture and product design. You’ll see Schwinn bikes, Muhammad Ali, Hank Williams, Hershey Bars, Bugs Bunny and Ben Franklin in there. They all represent the wonderful, crazy and inventive grandeur of America. What’s more, the way in which the images are uniquely juxtaposed in the book really makes Americans think about who we are, what we stand for, and perhaps, where we should be heading.

9. Where do you find inspiration year after year? How do you keep things fresh?

I love music and film. I love sports. I love to travel. And I love my children. They are a constant source of inspiration and help keep my feet on the ground. I also love to walk around the streets of New York, the city attracts creative people from all over the world and the result is this wonderful front of new ideas. If I ever find myself uninspired, I just take a little stroll with my eyes and ears completely open. Fashion, art, music, entertainment; it’s all happening all the time!

10. What is the “Tommy Hilfiger Lifestyle?” And how has it evolved over time?

We’ve been building on what we started with; the foundation is exactly the same. Classic American Cool was my approach to menswear, and our womenswear collection was built on the same foundation. Every product and collection I create is projected through the same lens and design sensibility. Creating a lifestyle brand was really about sharing all the things I love in life with people, whether it’s a classic with a modern twist, or music, art, film, publishing or sports. All of these things form a piece within the Tommy Hilfiger lifestyle and culture because these different elements are simply the things that I love-the things I want to be part of, and the things I love to share.

11. With an amazing 25 years behind the brand, what lies ahead for Tommy Hilfiger now?

I’m so excited about continuing to take American prep global! I love that so many people around the world wear my designs and have a taste for great American classics. My Icon collection is the perfect way to celebrate 25 years of the brand. Looking forward, I also hope to continue my charitable efforts. I find giving back to those less fortunate very rewarding and am honored that my success over the past 25 years allows me to make a difference beyond the world of fashion.

Here are some of our picks of classic pieces from Tommy’s collection inspired by his favourite style icons.

Inspired by the great American cowboy boot, these ankle boots are made of super-soft leather and have a wooden stacked heel as well as iconic ribbon detailing.

This legendary barracuda jacket has a snug, elegant silhouette and is made from woven cotton lined with tartan, and sports the US flag on its sleeve.

A shirt with class and flair that’s made with an antique wash in a Bengal stripe.

Every man needs a good blazer in his wardrobe. This version is modernized with sleek lines and cool details. It lends instant smart elegance that’s perfect to wear to any occasion.

This low-cut, straight-leg jean accentuates a woman’s curves in all the right places. Exuding a vintage look that’s finished with a stonewashed effect, this pair of jeans is made with a v-shaped sliton the rear waist. Pair it with a t-shirt for the ultimate relaxed style or with a white shirt and a blazer for a smart yet casual look.

The ultimate American classic, this cool motorcycle jacket displays the American flag on the side of the sleeve as a nod to the brand’s heritage, next to a red zipper and a tartan lining finished with a quilted effect.

Finding the right tee is always a challenge, but with this classic white tee featuring edgy artwork, the search is no more.

This iconic sailor neck sweater offers crisp and casual refinement. Beautifully knitted in white cotton the sweater features brass buttons and the brand’s 25th anniversary ribbon detailing on its cowl neck. Inspired by classic, American nautical chic, this sweater keeps you looking perfectly and effortlessly pulled together.

This tartan tunic with ruffles is for the woman on the go who dresses for comfort and style.

Executed in red, white and blue, this cardigan, made from wool and cashmere, features the stars from the American flag on its back.

This preppy and cool sweater cardigan features iconic stripes on its neck and button and a lettered ‘H’ on the front pocket.

Made from soft light brown leather with suede trims and iconic ribbon detailing, this exquisitely crafted bag is perfect for the three-day weekend.

The iconic wool coat stands the test of time because of its outstanding design. The perfect length, weight, color and fit, it’s sharp looking and functional. This pea coat is modernized with a streamlined silhouette and super-soft, wool nylon. The blue lining is an unexpected twist on a much-loved classic.

The wristwatch is a cult classic you need right now. This elegant timepiece is cool and modern made with a grosgrain strap with iconic ribbon details.

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