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From all the brands we wear daily, how much we know about them. And how much we know in order to get inspired and motivated by their creators and all that they have done to celebrate individuality, well-manufactured items and a lot of hard work behind it.

One of the stories that caught my attention the most has been @TommyHilfiger who started his own business at 17 years old selling only jeans, a small business that evolved into a store at his basement selling candles, clothing and all things rock’n’roll to already famous people like Bruce Springsteen.

My first Tommy was a perfume -honestly-. The classic “Tommy Girl“, my dad gave it to me as a present when I turned 15. It is magic for the senses. If you are a classy girl, you must go for it.

People’s Place -Hilfiger’s shop- went bankrupt when Tommy was only 25 so he decided to study commerce before launching his own label in 1985. As a designer, his first motivation came from his desire to update the stiff preppy clothes of his youth that he disliked wearing as a young man such as “boring khakis and ill-fitting button-down shirts.” He realized that classic looks needed a contemporary spin.


Honestly, Hilfiger didn’t possess any extraordinary talents or an academic background that would propel him to success. He is the second of nine children, who grow up in Elmira (New York) idolizing rock stars like Mick Jagger, as all the rural humans do. When he was in his early 20s, he was an aspiring entrepreneur struggling to break even and had to file for bankruptcy. Like many these days.


In his own words that near crisis taught him an important lesson about money: “You have to know your company’s numbers inside and out. Some people learn a lesson and then make the same mistake again, I tried very hard not to make the same mistake twice.”

American Dreamer by Peter Knobler.


From his style and his personal achievements and failures, here are 5 things we ALL can learn from Tommy’s life and career:

Care for the business.

Hilfiger brought fashions from inner-city New York and sold them in his first store People’s Place. He was in love with UK rock bands, such as The Beatles, The Rolling Stones, and The Who, so he made it his business to bring those looks of the day to young America. He bleach dyed denim bell-bottom jeans, he found bongs and beads and sold them and all that was part of the culture in his thriving shop. With the look came the lifestyle. He had to be a part of the scene and right in the middle of it was where he lost sight of the business and finally had to file a Chapter 11.

Is nice to be in the eye of the hurricane but better be in the eye of your business, keep the core.

Take on the challenge.

Before the making of his lifestyle brand, Hilfiger worked at some fashion companies and took on freelance design assignments. He landed a job at Calvin Klein brand just 4 days before he was to fly to Hong Kong to take on the role, businessman Mohan Murjani approached him saying he wanted to back an American menswear designer. Hilfiger had a choice: go and work for Calvin Klein or compete with the powerful fashion label, then it all started.

We all have the power of decision, and usually, the hardest and risky ones are the ones that pay the most. Don’t be afraid to choose.

Stick to your knowledge.

There are designers and there are brands. Tommy -who is not a designer- knows how to threat his label as a brand. Powerful runaways, refreshing styles, attractive models, high-end partnership, connection with amazing creatives. TH has been always on top by cherishing the style and mixing the high-end background with clothing production. And many people said at the time he would not make it because he wasn’t a designer like YSL or Chanel. But he has done and remains to do it. Tommy Hilfiger is always on its roots.

Learning to craft the back end of your business is primordial to go on a long run and escalate. Craft your own recipe.

Watch the other way.

Hilfiger knows best about casual dressing. When he launched the brand in 1985 with a menswear line that included oversized shirts other labels were offering fitted looks. He was always on the other side of the road. Then, street fashions were hot at the time but Tommy went another way and launched his H line with luxury fitted pieces. Hilfiger famously said that it worked because “they were zigging and we were zagging”.

If people are doing one thing and you see the room too crowd, go the other way. There is plenty room for you if you know how to fill it.

Have Fun.

The brand has always been a celebration of being carefree, youthful and happy. It is a brand that doesn’t take itself too seriously and makes us think of shiny happy people.

Share a motivation, an idea of a feeling people can follow.


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