If you’ve seen the cover of my latest book, Pretty Powerful: Beauty Stories to Inspire Confidence, you’ve seen our hot pink skateboards (so rad, right?). The inspiration for the original Pretty Powerful skateboard on the cover came from wanting to empower women to try something that isn’t typically thought of as a woman’s sport. We wondered: what better way to celebrate Pretty Powerful’s confident spirit than getting confident on a skateboard? Our friends over at The Cools thought so too.

Cut to the basketball courts of Tompkins Square Park in NYC’s East Village and pro skater, Eli Reed. His task? To teach a bunch of fashionable newbies how to skate in two hours’ time.

 

So who showed up to learn some ollies? (Ok, ok, Eli started with them simply standing on the board.) It was a who’s-who list of names from fashion and entertainment, including Tales of Endearment’ blogger, Natalie Joos; model Jessica Hart; Refinery 29’s very own Annie Greenberg; Kat Stoeffel, NY Mag’s associate editor of The Cut; The Man Repeller’s Leandra Medine; entrepreneur-dj-model, Hannah Bronfman; Logan Horne, star stylist; art director, Sugar Vendil; Harper’s Bazaar editor, Chrissy Rutherford and from HBO’s “True Blood”, Anastasia Ganias— all of them from The Cools’ uber-cool roster of stylemakers (who you can follow and shop through their social marketplace).

(Fun fact: our pal, Harry Beee—yep, that’s three Es—made the skateboarding 101 suggestion after spying us assembling the neon boards in our SoHo office from his own digital agency, The 88, across the street. Neighbors are so nice, don’t you think?)

Check out The Cools behind-the-scenes video to see how our 10 Pretty Powerful skateboarding friends did.

Photos & Video by The Cools