Shailene Woodley Dazzles In Pink Jumpsuit & Big Blue Hat At Kentucky Derby With Fiancé Aaron Rodgers — See Pics

Shailene Woodley and Aaron Rodgers made a regal appearance at the Kentucky Derby alongside friend and former 'The Spectacular Now' co-star Miles Teller!

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After COVID-19 wrecked the traditional “Run for the Roses,” the Kentucky Derby was back to (sorta) normal on Saturday (May 1). Churchill Downs was open, and a limited number of fans were allowed to watch the “fastest two minutes in sports” in person. Among those gathered was none other than Aaron Rodgers, but he wasn’t alone – as both Aaron, 37, and fiancée Shailene Woodley attended the event. The couple popped up in photos posted by her close friend Miles Teller‘s wife Keleigh Sperry.

Shailene looked ready for a day at the races in a gorgeous bubblegum pink jumpsuit, paired with a large baby blue hat. The accessory featured a big bow on top. For his part, Aaron looked dapper in a suit and top hat as he stood behind her in the group photo. The NFL pro accessorized with a old school black hat and aviator sunglasses, finishing his look with a fresh pair of white sneakers. “Down N Derby,” Keleigh posted in her caption. It’s so sweet to see the close friendship between Miles and Shailene going strong nearly 8 years after their film The Spectacular Now.

Though Aaron is a California native who’s spent the last fifteen years playing for Green Bay, Wisconsin, the Kentucky Derby has become somewhat of a tradition for him. From 2014 to 2019, Aaron would attend the game with “a group of buddies – mostly teammates past and present” – according to the Green Bay Press-Gazette. In 2019, Aaron shared a photo of him with “The Crew” in Louisville, posing along with David Bakhtiari, Davante Adams, Bryan Bulaga, Corey Linsley, Jimmy Graham, Randall Cobb, and A.J. Hawk.

Aaron was also seen taking his “crew” to the 2018 race, where he bet on racehorse Audible (who ultimately came in third.) He and fellow quarterback Tom Brady (who is also known to be a Derby fan) bumped into each other during the 2017 event, as captured by Katie Couric, of all people. This wasn’t the first time Tom and Aaron hung out at Churchill Downs. The two were spotted at the 2014 event, per the Courier-Journal.

 “I plan the weekend and send out an itinerary to everyone in the group,” he told the Courier-Journal in 2019. “We like to get to the track early and spend the entire day at the Oaks and Derby.” Had the COVID-19 pandemic not ruined every major sporting event in 2020 – the Derby was rescheduled to September and held in front of no fans – Aaron probably would have kept his streak alive.

It should be noted that Aaron usually turns the Derby into a guys’ trip. When Aaron was romantically involved with Olivia Munn and Danica Patrick, he didn’t bring either to the Derby with him and “the crew.”

Aaron Rodgers revealed in February that he and Shailene Woodley were engaged (Shutterstock)

Ahead of the Derby, Aaron caused quite a stir when ESPN and multiple other outlets reported that he was “so disgruntled with the Green Bay Packers that he has told some within the organization that he does not want to return to the team.” Reporter Tom Pelissero also tweeted that “The [San Francisco 49ers] reached out to the #Packers on Wednesday about trading for Aaron Rodgers, but no formal offer was made, and a source said there is a ‘zero percent chance’ that Green Bay deals the reigning NFL MVP.”

Sadly, the moment this report broke, Shailene Woodley’s name began to trend alongside Aaron’s on Twitter, as many seemingly blamed her for the decision (and not the fact that despite Aaron winning the NFL MVP, the Packers haven’t been to the Super Bowl since 2011). It was a similar wave of misogyny that Olivia Munn faced when she and Aaron were together.

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