Drake just proved that nothing is impossible. While sitting front row at rumored girlfriend Serena Williams' Signature Collection by HSN Spring 2016 fashion show on Tuesday, Sept. 15, Drake made famously stoic Anna Wintour crack up, and there's actually photographic evidence.
The "No New Friends" singer, 28, definitely has a new bud in the fashion industry, judging by the way the Vogue mogul, 65, was smiling.
Wintour, in her signature blunt bob, wore a green, geometric sheath dress with a matching statement necklace and her signature shades to attend the show, while Drake went with an all black ensemble.
The dynamic duo talked for the entire presentation and were both beaming for the duration of the event.
Williams, 33, wearing a plunging black bodysuit with a black fringe skirt and matching stilettos, revealed that Wintour has been her fashion mentor. "I have been working really closely with Anna and she’s been so amazing helping us out with the whole collection. I have a great team as well," she told Us Weekly at the event.
The tennis star's runway was also attended by other certified fashionistas, including model of the moment Gigi Hadid, in a white two-piece crop top and pants with a tan suede trench-vest and nude heels, who sat on the other side of Wintour.
Taylor Swift squad member Lily Aldridge also sat front row at the event in a similar color scheme of nude and white, choosing a long, light maxi with a fringe-covered suede jacket, and strappy sandals for the event.
What do you think made Anna Wintour laugh? Tweet with @UsWeekly using the hashtag #stylebyUs!
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