Conan O’Brien may be a California man now, but he’ll always have a little piece of Harlem. The talk-show host brought Conan to N.Y.C. for a week of shows at Apollo Theater, and the series has already been a delight. From taking the “New York City citizenship test” with Jon Stewart (“Where in New York City is the ball dropped every year?” “Citi Field.”) to debuting the Law & Order “dead body tour,” the show is thriving in the city Conan once called home. But ever since the host tweeted that he’d be getting a makeover from Dapper Dan, the Harlem-based clothier who has dressed hip hop legends like Salt-N-Pepa and Run DMC — and famously been, shall we say, emulated by Gucci — we’ve been anxious to see the results.
— Conan O’Brien (@ConanOBrien) October 9, 2017
Finally, the show revealed Conan’s transformation, and it did not disappoint. First, Conan got “Harlem Swag” tips from Dan, and then Conan was set free to try to dress himself. How did he do? Comedically, great. Sartorially, not so much. “Is this a Pee Wee Herman special we getting ready to do or what?” Dan asked, of Conan’s first look, which included a sequin pattern jacket, matching bowtie, red fedora and sparkly loafers.
Conan’s second attempt was even less successful. Inspired by Dapper Dan’s all-plaid look, he chose multiple plaid pieces in various colors, a straw fedora and floral shoes. “You think I look like a pimp?” Conan asks, to which Dan responds, “You look like someone trying to be a pimp.” Burn.
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Conan’s third — and most hilarious — outfit features a sheer bomber jacket worn as a shirt, a fur coat, splattered jeans and red combat boots. Dan’s critique: “It looks like you was nominated for five BET Awards, you wore five outfits and you wore all of them at the same time.” Can we get this man his own show already?
After a brutal but fair second opinion on the street (“I don’t like it.”), Conan decides to leave the styling to Dan himself. And finally, the two walk out on stage at the Apollo, and the final look is nothing short of menswear brilliance. There’s even a cane! Watch the full segment in the video above.
What do you think of Conan’s makeover from Dapper Dan? Let us know in the comments!