In 1996, R&B star Aaliyah became the face of Tommy Jeans. In her TV ads, she wore a red, white and blue bandeau top and baggy jeans that ran an oversized Tommy Hilfiger logo down one leg. The outfit came to define the brand’s massive ‘90s moment: Over the course of the decade, Tommy Hilfiger’s sporty denim collection was worn by Kate Moss on the runway, Snoop Dogg in his music video, and Britney Spears on her first tour.

In the years since, Tommy Hilfiger’s Tommy Jeans division faded out as the brand shifted toward a more mainstream aesthetic. It went from an edgy brand to a “Macy’s brand,” said Jessica Navas, chief planning officer at agency Erwin Penland, selling everything from polo shirts to home goods through the department store and other wholesale partners.

Amidst a revived obsession of ’90s fashion, Tommy Jeans returned on Monday with revivals of its past-era Dungaree overalls, short-sleeved cropped sweatshirts, oversized jean jackets and the red, white and blue bandeau, all featuring the iconic brand logo. Exclusively sold through Urban Outfitters, the collection retails between $45 and $199 and is the first release of an ongoing partnership that will also include a men’s collection and a spring collection due next year.

Tommy Jeans for Urban Outfitters is the retailer’s latest partnership with a brand that brings with it a wealth of nostalgia capital resonating from the ‘90s. It also sells exclusive collections from Calvin Klein, Wrangler, Fila and Adidas Originals, all of which hit on the same throwback fashion trends that are popular today: cropped T-shirts and sweatshirts with minimalist logos, loose, high-waisted jeans, white sneakers and chokers.

“These partnerships put Urban Outfitters in a trend-forward space while legitimizing its role there,” said Chris Gilbert, senior social media strategist at the digital agency Kettle, which works with retailers like Aldo and Sephora. “This helps drive sales while serving as a strong branding play.”

After a long time slump, Urban Outfitters, Inc. (which also owns Anthropologie and Free People) reported that, for the first quarter that ended on April 30, its namesake brand’s sales climbed 2 percent to $299 million, with wholesale revenue climbing 16 percent, to $62 million, improvements that the company attributed to factors like improved product selection and fewer price markdowns. 

But it’s not just a score for Urban Outfitters. The relationship is mutually beneficial.

“These ‘90s brands are struggling,” said Gilbert. “They used to be associated with urban culture, but they’ve had a hard time building a young, hip audience in recent years. Now that street style is being received by the masses, these brands get to own the fact that they were the ones originally to play in the space.”

In an announcement, Urban Outfitter’s president of North America Trish Donnelly said that the company was focusing on defining trends with “greater conviction.” While riding the resurgence of these original brands, Urban is at the same time curating how the trend is packaged and sold today. The pieces in each collection are picked and styled by the Urban Outfitters product team, and the result is an instantly recognizable yet modernized version of the ’90s vibe.

“It’s the new retro. Urban Outfitters knows how to style these trends for a specific customer, and in turn, these brands give it a certain gravitas,” said Navas. “They’re reinterpreting the ‘90s, but it feels curated for now. At Macy’s, it doesn’t feel cool. It feels old.”

Urban Outfitters has taken a specific portion of the Tommy Hilfiger and Calvin Klein brands — the ’90s, streetwear, urban inspired divisions — and pulled together items that, in a previous life, were worn by Mark Wahlberg, Kate Moss and Aaliyah. Today, the branded crop tops, bras, jeans and sweatshirts are seen on Gigi Hadid, Kendall Jenner and Justin Bieber. It also wrangles together social media influencers in its user-generated content feed, pitching the old items in new, Instagram-filtered settings. That’s key to how millennials spend their money, according to Hilldun CEO Gary Wassner.

rainy Sunday with my boy

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“Pop culture has a tremendous influence on millennial shopping choices,” Wassner told WWD. “If it looks good on Gigi Hadid, then the millennial shopper wants it and seeks it out.”

Meanwhile, department stores like Macy’s that also carry Tommy Hilfiger and Calvin Klein don’t offer any point of view on the brands. A Tommy Hilfiger logo shirt on sale at Macy’s, similar to what Urban Outfitters carries, looks a lot less desirable in the mix with Tommy Hilfiger-branded bedding and a cable-knit cardigan beside it.

“I’m sure the Macy’s of the world are kicking themselves watching Urban Outfitters enjoy this Tommy and Calvin renaissance,” said Gilbert. “But the nature of their business is much more mass, and they have to be more watered down to appeal to more markets.”

Urban Outfitters will see a halo effect across its broader product assortment, said Navas, as exclusive, limited time collections bring customers into the store. And while vintage loyalists may sneer at seeing a rare edition, original Tommy Jeans denim jacket on sale at Urban, which has a reputation as the “sell-out” point for underground brands, it’s claimed a certain territory here.

“Everyone else is doing knockoffs, Urban Outfitters has the actual thing,” said Navas. “That excitement and attention is going to spill over to the company itself.”