So, Why Exactly Is Everyone Freaking Out About Gov. Ron DeSantis’ Boots?

AP Photo/Charlie Neibergall

The third Republican primary debate is scheduled for next Wednesday. While most candidates would like to be talking about policy and their perceived path to victory ahead of the event, the DeSantis campaign has been left to answer questions about… the Florida governor’s boots. 

On Thursday’s show, Megyn was joined by RealClearPolitics co-founder Tom Bevan and Ruthless host Josh Holmes to discuss the obsession with DeSantis’ footwear and why he doesn’t just nip the controversy in the bud.

Footwear Faux Pas

If you’ve seen DeSantis on the campaign trail, you’ve likely seen him in what has become his trademark cowboy boots. He has multiple pairs in multiple colors that he wears with everything from jeans to suits, but the one thing that stays the same is the heel height. The boots add about two inches to the governor’s reported 5-foot 11-inch frame. There has been some speculation, however, that hidden lifts inside the shoes are actually making DeSantis appear even taller.

Earlier this fall, Donald Trump suggested on Truth Social that his 2024 GOP challenger was wearing “hidden heels” during an appearance on HBO’s Real Time with Bill Maher. On Tuesday, Politico published a feature by menswear writer Derek Guy titled 3 Expert Shoemakers Say Ron DeSantis Is Probably Wearing Height Boosters – an in-depth expose on how the Florida governor is artificially inflating his height.

The experts – who Politico pointed out were not paid for their analysis – apparently looked at various photos and videos of DeSantis and determined based on the “unusually high wrinkle” in the governor’s boots, the “unusually taut” instep (i.e. the area of your foot where shoelaces usually sit), and the curled toe bed that the interior of the shoe has likely been manipulated. Austin-based cowboy bootmaker Graham Ebner told Guy it looks like “his foot is being lifted up and stretching out the leather.”

During an awkward exchange on Patrick Bet-David’s podcast on Monday, DeSantis denied the allegation that he’s wearing lifts, instead saying his preferred footwear is “just standard, off-the-rack Lucchese boots.” His press secretary, Bryan Griffin, took the denial even further. His statement to Politico read, in part: “The governor doesn’t pad his boots, but if he ever needed anything to line a pet cage or fold up and wedge under a table leg, that would be the highest and best use for Politico Magazine.”

DeSantis on His Heels

Political campaigns are, in Holmes’ words, “brutal” and often require candidates to not just present policy positions but also to be ready for jabs from opponents that are meant to distract. Trump has been “really, really good at doing this,” Holmes said, while DeSantis seems to “have some sensitivity” to doing it back. 

That dynamic is on display here. “When you have one side that is willing to deploy every tactic in the book and get the national conversation about whether he’s wearing lifts and you’re not willing to say, like, ‘I’m gonna take my lift and shove it up your fat ass,’ it’s a one-sided discussion and you can never get out of it,” Holmes explained. “It’s not trying to be a pun, but [Trump] has had [DeSantis] on his heels.”

Megyn said honesty is the best policy here. “I think if I were a guy in his position and I did not have lifts inside the boot, I might actually take off the boot and show it to Patrick Bet-David,” she said. “It’s a little beneath the dignity, but it would have put it to rest once and for all.” Alternatively, he could own it. “Another route could be… ‘I do wear them. I’ve always been kind of sensitive about the fact that I’m not a little taller. You caught me in my insecurity. Maybe other guys out there can relate,’” she suggested.

While DeSantis is not necessarily known for his sense of humor, Holmes joked that he could have some fun with it. “He could come out on the next debate stage on stilts or something and just make the whole thing a clown show,” he concluded. “I’m sure people would love that.”

You can check out Megyn’s full interview with Bevan and Holmes by tuning in to episode 661 on YouTube, Apple Podcasts, or wherever you like to listen. And don’t forget that you can catch The Megyn  Kelly Show live on SiriusXM’s Triumph (channel 111) weekdays from 12pm to 2pm ET.