Ken Jennings is ready to wager on "Terrible Clothes" for a cool $1,000. The beloved Jeopardy! host took a nostalgic stroll down memory lane, revisiting the eclectic wardrobe choices he made during his record-breaking 74-game winning streak in 2004. And let's just say, Ken wasn't exactly thrilled with his past sartorial decisions.
"If my eyes don't deceive me, that's a truly hideous tie," Ken mused in a video shared on Jeopardy!'s Instagram on September 22, as he scrutinized a clip of himself from 21 years ago donning a beige shirt paired with a vibrant, Coca-Cola bottle-patterned tie. "And honestly, it's a shirt color I'd never go for these days." Labeling the ensemble as "truly unfortunate," the 51-year-old quipped, "I feel like I should be rocking some cozy sweaters instead."
Ken's next fashion faux pas featured a pinstripe jacket layered over a cream-colored shirt and a fuchsia tie, which the former software engineer revealed was part of his collection of "cheap dollar ties" acquired during his stint in South Korea. "You could snag knockoff threads on the cheap," Ken explained. "I bet none of these ties cost more than, say, $3 American. And it definitely shows."
Another outfit, consisting of a maroon shirt matched with a striped, olive green tie, prompted the Jeopardy! champ to remark on the outfit's unappealing coordination. "It's like they clashed in the worst possible way," he marveled.
Reflecting on his past style with a hint of embarrassment, Ken confessed that he resembled "some kid raiding his dad's closet." "I was just trying to mix things up as much as possible," he explained. "I thought, 'Oh, you don't want to repeat the same six shirts. The audience will catch on to that.'" The host jokingly added, "So, instead, I opted for new, even worse shirts."
Questionable fashion sense aside, there's another aspect of Jeopardy! that still gives Ken—who took over hosting duties following the passing of Alex Trebek in 2020—the heebie-jeebies. "I have to admit," he shared on the Lovett or Leave It podcast in August, "as a kid, I found the Jeopardy! interviews so cringeworthy that I'd actually leave the room. That's my Jeopardy! origin story."
That's why Ken now strives to "make it the least cringeworthy it can be" and wrap up the interviews as swiftly as possible. "I've spent my whole life perfecting the art of escaping conversations in 25 seconds," he quipped. "That's why being the Jeopardy! host is the perfect gig for me."
