The Story Behind 'SNL' Host Woody Harrelson's "Fashionista" Look

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Woody Harrelson on 'Saturday Night Live'

In a surprise reveal of his inner "fashionista," Harrelson literally ripped off his classic black tux to unveil a sleek, satin pajama set custom-made by hipster Harlem-based haberdasher Dapper Dan.

During his opening monologue as host of the 45th season premiere of NBC's Saturday Night Live, Woody Harrelson literally ripped off his tux to unveil a custom satin pajama set underneath created by the uber-cool upscale streetwear designer Dapper Dan.

“I’ve been working for a long time and, I’d like to tell you, I’m the same old Woody you know and love. But never before in 34 years since the mantle of fame was thrust upon these over-broad shoulders have I been what I am now: a fashionista!” he said coyly in his monologue.

“I mean, look at me, I’m a damn cover boy!” Harrelson continued as a shot of the actor on the cover of Esquire magazine’s September issue shared the screen. “The best-dressed list is new territory for me. I’ve been on the worst-dressed list many times for good reason! You know, I never used to think about what I wore. I guess I was anti-fashion because it always seemed to me like there were more important things to focus on: The ice is melting; the Amazon is burning; our water, food and air are polluted. But now that I’m a fashionista, all that’s forgotten. Because now I care about one thing and one thing only — looking good.”

“So I asked my buddy Dapper Dan to realize my dream of the ultimate in eveningwear," he added. "And I am not talking about this tux, by the way.” That being said, Harrelson literally ripped off his tuxedo, exclaiming, “Pajamas, the time has come!” 

While Daniel Day (a.k.a. Dapper Dan) was attending Paris Fashion Week and unavailable for comment when The Hollywood Reporter reached out, a spokesperson for him gave THR the backstory on Sunday, saying that Harrelson contacted the Harlem-based haberdasher about two months ago: “Woody had a clear vision that he wanted his clothing to match the monologue; he wanted to make a strong statement. He had this pajama idea, getting away from a traditional formal look.” Dapper Dan made three custom sets of pajamas for him and “it was a game-time decision on which one he was going to wear.”

The host ended up wearing a deep-blue satin pajama set with a pattern of red bees, golden stars, yellow piping and luxe golden lining. While the designer’s representative would not reveal details of the other options, he did say that Harrelson always asks for natural versus synthetic materials.

Turns out that the actor connected with Dapper Dan years ago through their mutual friend, screenwriter Frankie Hyman, who hails from Harlem and with whom Harrelson also collaborated to write the off-Broadway play Bullet for Adolf in 2012, an account of their meeting in 1983 and continuing friendship, which Harrelson also directed.

Dapper Dan posted a video of the fashion moment on Instagram, adding, "I guess white boys can jump! LOL." 

We're looking forward to the next chapter of Harrelson rolling out his inner fashionista.