Which pieces resonated with the hip-hop community?

In the early 90s, hip-hop artists like Grand Puba, DJ Alamo and Snoop Dogg started wearing rugby shirts, polos, T-shirts and large sailing jackets. Denim became hugely popular during the mid-90s.

Collections included bright synthetics and leather - popular materials that were becoming increasingly associated with the hip-hop aesthetic. Original TOMMY HILFIGER designs in bold and bright nylon were a big part of the 90s and early 2000s Tommy Jeans look. The kind that TLC came to love. It captured the hip-hop attitude and relaxed vibe.

What were some of the key denim styles that resonated at that time?

Naturally with denim, big baggy mid-wash jeans resonated with the hip-hop style. Details on pants included the carpenter loop. Red, white and blue features on the sides and waistbands became a hip-hop signature. Contrasting pockets and waistbands with bold TOMMY HILFIGER lettering featured heavily.

Dungarees became an influential look in street style with the classic flag or red, white and blue typing. Cargo jeans and shorts became synonymous with the hip-hop vibe. One type of denim was so associated with an icon of the time it became known as the ‘Aaliyah jean’. A wide leg denim in red, white and blue with contrasting lettering.

Which other styles were popular with the hip-hop community throughout the 90s and 00s?

TOMMY HILFIGER sneakers which launched in 1996. The sailing category with its bright colors, large logos and athletic style. TOMMY JEANS introduced overalls and coveralls in both cotton and denim, as well as bright colored synthetic fabrics.

By the early 2000s TOMMY JEANS delivered more of a contrast in sizing. While the womenswear still included large oversized menswear, shorter shorts and cropped tops started to become more popular. Beading and metal studs become common embellishments. The 2000s saw a rise in full matching ensembles.

Tommy’s background in music and fashion:

“Music is at the core of who I am and has always inspired my designs. I first got into fashion because I wanted to dress like my favorite rock stars. My vision was always to reimagine classics – to take iconic pieces and give them a fun, youthful twist. I wanted to create new American staples that drew inspiration from culture, art, and music all at the same time.”

Tommy on the emergence of hip-hop coinciding with his brand:

“When hip-hop came onto the scene in the 90s street style exploded in popularity. Our original designs had bold, bright colors, oversized looks and playful prep. It captured the hip-hop attitude and relaxed vibe and we noticed rappers started wearing our pieces. My brother Andy was dialed into the music world and became instrumental in helping us make connections because he understood the scene. We were quick to embrace pop culture and give our clothing to rappers when they said they liked it. It turned out we were doing product placement before the term was even invented. Hip-hop brought a fearless style and we wanted to be part of it.”

Tommy on being embraced by the hip-hop community?

“I founded my brand with an inclusive vision and spirit. We loved seeing different cultures put their own spin on dressing and disregard fashion’s traditional rules. When the hip-hop community embraced our brand in the early 90s they styled it in new ways, like wearing oversized pants and jackets. This inspired us to develop TOMMY JEANS bringing in Kidada Jones, Quincy Jones’ daughter, to create for this new movement. TOMMY JEANS was for a younger audience, with brighter, baggier styles and bigger, bolder branding. A collaborative response to the way the hip-hop community was connecting with the brand. We played with conventions, putting women in menswear, letting go of the traditional rules of dressing. In the early iconic Aaliyah campaign she was wearing a bandeau created from a pair of men’s briefs, cut and tied at the back. She embodied the cool and sexy femininity that emerged from the women of hip-hop"

Tommy on co-signs during the 90s golden age

“We worked with innovative artists in the cultural movement. Grand Puba was the first to call us out in lyrics and spread the word across the streets. Snoop broadcast the brand to the world on Saturday Night Live. And we dressed some of the most exciting rap and R&B stars of the time including Puff Daddy, TLC, Destiny’s Child and Wu Tang Clan. We just had so much fun during that time.”

Andy Hilfiger on the London Fashion show, 1997

“We invited fashion editors and brought hip-hop to the stage. We had Treach from Naughty by Nature rapping while wrapped in a Tommy flag, then Naomi Campbell and Kate Moss came out and it was like a dance party on the stage. The English press was asking ‘What’s going on?’ We took this theme around the world and did it in Japan with Total and Da Brat.”

Andy Hilfiger on clashing cultures as punk inspired hip-hop shows.

“Tommy said we should do a punk show, but with hip-hop. There was a punk band we loved called the Dead Boys we used to see at CBGB’s in the 70s. They had an album called ‘Young, Loud and Snotty’, so we did a hip-hop show called ‘Young, Loud and Sexy’. It was very Sex Pistols. Mary J Blige came out in a pink leather thing with studs. We had Mark Ronson DJing, and Q-Tip also on stage. It was at the Hammerstein Ballroom on the upper floor and the elevator broke so all the guests got stuck in the elevator. It was all done last minute but it became the hottest show around.”

Andy Hilfiger on the ad-lib creation of Aaliyah’s iconic bandeau

“My friend had a new artist and said she has an album out and she loves Tommy. Aaliyah comes into the office. We asked her, “Do you wanna model? We have a Tommy Hilfiger Show coming up that’s going to be like the Vibe fashion show. That was the first time she modelled for us when she was 17 or 18. Usher, Wu Tang, and Quincy Jones were all in the show. A few months later, we were doing a photoshoot for the second campaign of Tommy Jeans. We didn’t have many women’s samples, but we had a lot of men’s. So we were on the roof of a studio in LA with Kidada Jones, our stylist.

She was putting Aaliyah in boxers with baggy jeans - all men’s clothing. We took a pair of briefs – cut the crotch out and put it on as a bandeau. The ‘Tommy’ was upside down as it was improvised underwear. In some of those photos the bandeau was underwear – and the look became iconic. And you still see that look today with GloRilla, who nodded to it in the Tommy x Aries campaign.”

Andy Hilfiger on interacting with hip-hop culture

“We had a music department and a street team just like the record companies did. So we were working the same way as the hip-hop community. Puffy was the best at that. Going to the streets and handing out CDs. We were there handing out hats and bags. It was a different way of working. It led to us being one of the first commercial US brand to be in magazines like Vibe, The Source, XXL, Complex and Slam.”