Ken Jennings Roasts His Jeopardy! Outfits Over the Years

Ken Jennings may know pop culture, but style is another story.

A recent video shared on the Jeopardy! Instagram account showed the 51-year-old contestant-turned-host reflecting on his least favorite outfit choices during his early days, whizzing through questions on the long-running game show. 

“If I’m seeing that right, that is a terrible tie,” Jennings said in the social media clip while watching himself be introduced as a contestant circa 2000 by the late Alex Trebek. “And really, it’s a color of shirt I would never wear.”

Footage showed the 74-game Jeopardy! winner wearing a tan, long-sleeved, collared shirt with a colorful neck tie decorated with vintage glass Coke bottle designs. 

“I guess if you like Coca-Cola, like, you’re into that outfit. That’s really unfortunate,” he added. 

Jennings then had a suggestion for his past self. 

“I feel like I should maybe be wearing… maybe some sweaters,” he added before moving on to another look that he deemed slightly better than the one prior. “At least there I’m wearing a jacket.”

His next look consisted of a brown jacket with a light-colored dress shirt underneath. The former software engineer added a fuchsia necktie to top it off, though he admitted the pop of color piece likely cost him “no more than $3” when he bought it while living in Korea. 

“A lot of these were just kind of like cheap dollar ties, probably from when I lived in Korea, you could get knock-off clothes for cheap. I bet no tie here cost more than, say, $3, American. And it really shows,” Jennings joked. 

The game show host wasn’t done with his roasting session. 

Another one of his tops came in a deep shade of red and did seem to be to his liking. However, Jennings wasn’t a fan of the tie he paired with it, as it was patterned with “horizontal stripes, so it’s not exactly slimming.”

He also criticized his “thousand-yard stare” as he focused intently on the game at hand. 

“This is actually an okay look,” Jennings said. 

He continued, “It’s just a nice, striped shirt. The checkered tie is alright, but it still looks like some kid wearing his dad’s clothes — and not blinking.”

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Additionally, Jennings confessed that back then he would wear “new, worse shirts” so the audience didn’t catch on to him wearing “the same six shirts.”

Despite his own critiques, fans in the comment section couldn’t get enough of his reactions to the throwback clips. 

“If you don’t think Ken is adorable, there’s something wrong with you,” one person wrote. Another added, “Ken your brain + winningness > greater than fashion!! We loved you then and love you now!!”