Drake Makes Anna Wintour Laugh at NYFW Spring 2016, Achieves the Impossible

Drake and Anna Wintour at Serena Williams Signature Collection By HSN
Drake cracks up Anna Wintour at Serena Williams Signature Collection By HSN on Sept. 15 Thomas Concordia/WireImage.com for STYLE360

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.

PHOTOS: The many focused faces of Anna Wintour

Drake and Anna Wintour - NYFW (posing)
Drake and Anna Wintour attend the Serena Williams Signature Statement by HSN show during Spring 2016 Style360 on September 15, 2015 in New York City. Grant Lamos IV/Getty Images

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.

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Drake and Anna Wintour - NYFW (talking)
Drake and Anna Wintour attend as KIA STYLE360 Hosts Serena Williams Signature Collection By HSN on September 15, 2015 in New York City. Thomas Concordia/WireImage.com for STYLE360

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.

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Drake and Anna Wintour - NYFW (clapping)
Drake and Anna Wintour attend as KIA STYLE360 Hosts Serena Williams Signature Collection By HSN on September 15, 2015 in New York City. ( Thomas Concordia/WireImage.com for STYLE360

The dynamic duo talked for the entire presentation and were both beaming for the duration of the event.

Serena Williams - NYFW
Serena Willams attends the Serena Williams Signature Statement by HSN show during Spring 2016 Style360 on September 15, 2015 in New York City. Grant Lamos IV/Getty Images

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.

Gigi Hadid - NYFW
Gigi Hadid attends the KIA STYLE360 Hosts Serena Williams Signature Collection By HSN on September 15, 2015 in New York City. Thomas Concordia/WireImage for STYLE360

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.

Lily Aldridge - NYFW
Lily Aldridge attends the KIA STYLE360 Hosts Serena Williams Signature Collection By HSN on September 15, 2015 in New York City. Thomas Concordia/WireImage.com for STYLE360

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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