LOUISVILLE, KENTUCKY - MAY 03: Gail Simmons attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
I AM DELIGHTED. This hat was a paid partnership with Wisconsin Cheeses and this is exactly the kind of spon-con we need in these times. (They're auctioning the hat to benefit the Barnstable Brown Diabetes Center.) MORE CHEESE HATS. Your move, Royal Ascot.
Jonathan Owens and Simone Biles
LOUISVILLE, KENTUCKY - MAY 03: (L-R) Jonathan Owens and Simone Biles attend Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
They're very cute, together and separately. Fun fact: I wore this color in Heather's wedding. (I love it, lavender needs to come back.)
Shaboozey
LOUISVILLE, KENTUCKY - MAY 03: Shaboozey attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
A relief that Shaboozey continues to be 100% charming.
Carmelo Anthony
LOUISVILLE, KENTUCKY - MAY 03: Carmelo Anthony attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
Melo is joining the NBA on NBC team, hence his appearance at this event. This suit looks comfy. I look forward to seeing his on air outfits!
Izabel Araujo and Joey Fatone
LOUISVILLE, KENTUCKY - MAY 03: (L-R) Izabel Araujo and Joey Fatone attend Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
I might have done a blue tie on Joey?
Chris Tucker
LOUISVILLE, KENTUCKY - MAY 03: Chris Tucker attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
Thumbs up! I approve of glitter shoes on all people.
Mickey Guyton
LOUISVILLE, KENTUCKY - MAY 03: Mickey Guyton (L) attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
HOW CUTE IS MICKEY'S LITTLE BOY? I love him. (And it's very cute that their shoes coordinate.)
Richie Sambora
LOUISVILLE, KENTUCKY - MAY 03: Richie Sambora attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
Proof of life for Richie Sambora here! Always good to check that off the list.
Wilmer Valderrama
LOUISVILLE, KENTUCKY - MAY 03: Wilmer Valderrama attends Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
Wilmer low-key agitating for someone to cast him in the Gatsby musical. (I totally think they should stunt-cast Gatsby the way they do Chicago. It would be fun.)
Amber Mariano and Rob Mariano
LOUISVILLE, KENTUCKY - MAY 03: (L-R) Amber Mariano and Rob Mariano attend Kentucky Derby 151 at Churchill Downs on May 03, 2025 in Louisville, Kentucky. (Photo by Jeff Schear/Getty Images for Churchill Downs)
They got Boston Rob out of his Red Sox cap! IT'S A CHRISTMAS MIRACLE. This might be the one celebrity couple whose divorce would devastate me. STAY TOGETHER FOREVER, ROB AND AMBAH.
