Collaboration has taken over the modern streetwear market. Rarely a week passes by without some ultra-hyped collab hitting shelves, inducing all kinds of lust and FOMO. It wasn’t always this way, however. The concept of streetwear collaboration is one that only really began to gain mainstream momentum at the turn of the millennium – and it was typically a far more complicated affair than simply slapping a logo on a brand’s existing product.

Back in the 90s, only a handful of industry figures saw the value in working with influential identities outside the realm of professional sports – and even less understood its importance quite like Thomas ‘Tommy’ Hilfiger: the namesake behind the brand that stands as one of the greatest fashion success stories of the 1990s.
First Steps
Hilfiger’s fashion career began in 1969, when, at the age of 17, the New York native journeyed to Cape Cod, Massachusetts. Hilfiger, together with seven friends, rented an apartment for the summer and he soon wound up working at a local clothes shop. That same year, while still in high school, Hilfiger began to dabble in fashion design itself. Unofficially launching his first fashion brand in his hometown of Elmira.
Highs & Lows
In 1971, with a grand total of $150 to his name, Hilfiger made the all-or-nothing decision to open his first store, People’s Place. Although initially successful, prompting Hilfiger to open additional stores in upstate New York, such success would be short lived. Due in large part to Hilfiger’s lack of experience and a not-so-serious work ethic, his venture came crashing down in 1977, leaving Hilfiger to file for bankruptcy at the age of just 23.
From Man to Brand
Downhearted and defeated, Hilfiger took a step back following the collapse of People’s Place. He spent the late 70s and early 80s working both for and with other labels, such as Jordache Jeans, while also formally expanding his education in commerce and the business of fashion to ensure he would never repeat his previous mistakes.
In 1984, having well and truly proven his talents in the cutthroat world that is New York City’s fashion industry, Hilfiger finally received his big break. Approached by a businessman named Mohan Murjani, he was given the opportunity to launch a men’s sportswear line under his own name. The Tommy Hilfiger Corporation launched in 1985, along with its now-legendary logo. It was backed by a high-profile marketing campaign right out of the gate, including a massive billboard in Times Square – intentionally opposite key competitor, Ralph Lauren,
Major Success
Despite having proven integral to his eponymous brand’s debut, Hilfiger parted ways with Murjani in 1989. He had found a new financial backer in Silas Chou, the son of the founder of one of of Hong Kong’s biggest knitwear manufacturers. As part of this major shake up, former Ralph Lauren executives were brought on board to lead the brand and the new Tommy Hilfiger rapidly climbed from strength to strength. In 1995, Hilfiger was declared Menswear Designer of the Year by the Council of Fashion Designers of America, but his brand’s true success came from the strings being pulled behind the scenes.

Superstar Status
Inspired by a lifelong love of rock and roll, Hilfiger made sure that his brand, under its new structure, was closely entwined with the music industry. During the 90s, the brand sponsored music tours for everyone from Britney Spears to The Who’s Pete Townshend. In addition, an eclectic A-list of stars from across a broad spectrum either worked with the brand or were clothed by the brand. Engaging with artists considered at the apex of cultural conversation had become key to the brand’s strategy. Core to its success within this, however, was Hilfiger’s staunch belief in the authenticity of collaboration: that it should solely guide and execute an artist’s ideas, not induce an outcome through force or persuasion.
Hip Hop Hooray
While simultaneously working with squeaky clean pop stars like Britney Spears, Hilfiger’s undeniably preppy brand became an unlikely hit within the hip hop community. Its urban appeal was solidified by a name drop on Grand Puba’s 1992 single ‘What’s the 411?’, quickly garnering Hilfiger’s attention. He soon began supplying apparel to hip hop artists, who were drawn to the brand’s use of bright colours and over-sized branding.
The late R&B legend Aaliyah was featured in a 1995 Tommy Hilfiger campaign, later signing on as a brand spokesperson. It was also around this time that Tommy Hilfiger’s fashion shows evolved into star-studded spectacles that saw the likes of Naughty by Nature frontman Treach performing ‘Hip Hop Hooray’ alongside Kate Moss on the runway.

Although Hilfiger had already successfully captured the attention of a generation in the late 90s, his genius foresight even saw him planning to tap into the next from a young age. He worked with Nintendo to put out an official collaborative Game Boy Colour branded with its requisite logo front and centre.
The American Dream
When it comes to 90s fashion, few brands – if any – can rival the success of Tommy Hilfiger. It became the true embodiment of the American dream through sincerity and authenticity. People didn’t wear it because they were being paid to do so: they wore it because they wanted to.

The latest chapter in the Tommy Hilfiger legacy has just landed at Foot District with the launch of the Tommy Jeans Fall Heritage New Capsule Collection, available now in-store and online.