Tailor Daniel Day, better know as Dapper Dan, made his name outfitting ’80s hip-hop legends in custom outfits that were, at times, more than inspired by high fashion brands like Louis Vuitton and Gucci.

After previously working with artists such as Run-D.M.C., Salt-N-Pepa, and the Fat Boys, Dapper Dan welcomed Conan O’Brien to his Harlem store and helped him get “swagged all the way up and down.”

Predictably, Conan is the more eccentric of the two as he sets out looking for the most eye-catching outfits the store has to offer until Dan steps in and delivers his signature swag.

Watch the video above to see what garms Dapper Dan picks out for Conan (skip to 5:30 for the end product) and then check out our in-depth interview with the legendary stylist and fellow Harlemite A$AP Ferg.

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