The former businessman and political neophyte is running neck and neck with Terry McAuliffe, the longtime Democratic fixture who is seeking a return to the governor's mansion after serving one term from 2014 to 2018.
A Youngkin victory would be significant. It wouldn't just send tremors of fear through Democrats nationally, presumably making the party's agenda that much more difficult to get through Congress; it would point to a viable path ahead for the GOP in swing areas, one that keeps on board the Trump base while regaining lost ground with independents and suburbanites.
If Youngkin pulls it off, his sidestepping of Donald Trump will have been a huge factor. In a state like Virginia, you can't be anti-Trump and win a GOP nomination. But nor can you be pro-Trump, or too vocally pro-Trump, and win a statewide election.
Youngkin walked this tightrope with some deft maneuvering — get Trump's endorsement, but don't talk about him or invite him to the state — and by making mighty exertions to define himself in his own right.
For the longest time, he ran only biographical ads, the sort of spots that make hardened politicos roll their eyes — he worked as a teenager in a diner; he practiced basketball until he won a scholarship; he ran a business; he raised four kids; and he is, of course, nothing like a conventional politician.
Youngkin got criticized for running an issue-less campaign, but the spate of bio advertising meant his answer to the question, "Are you pro- or anti-Trump?" could be, "I'm Glenn Youngkin." And, he wanted everyone to know, that fundamentally means a nice-guy Dad.
What the red MAGA hat is to Trump, the fleece vest — a relaxed, suburban, let's-meet-at-Starbucks-after-the-kids'-soccer-game look — is to Youngkin. In his appearance for McAuliffe, Barack Obama accused Youngkin of falsely portraying himself as a "regular ol' hoops-playing, dish-washing, fleece-wearing guy."
President Joe Biden took a sartorial shot, too. He warned of multiple forms of extremism: "It can come in the rage of a mob driven to assault the Capitol. It can come in a smile and a fleece vest."
Youngkin has studiously avoided the electoral poison of a backward-looking obsession with the 2020 election. He was cagey about 2020 during the Republican nomination battle, then acknowledged the legitimacy of Biden's victory. When former Trump adviser Steve Bannon headlined a bizarre, pro-Youngkin event featuring a Jan. 6 flag, Youngkin called it "weird and wrong."
On the issues, he has fought hard on the typical Democratic turf of health care and especially education. Youngkin has hit on education from the beginning, whether it's COVID-driven school closures, the need to protect advanced learning, school safety or the fight over critical race theory.
McAuliffe shows cringeworthy dance moves at rally with Biden McAuliffe's statement in a debate that parents shouldn't tell schools what to teach brought these strands together in a powerful way and allowed Youngkin to portray himself as the protector of parental prerogatives. If McAuliffe loses, his parents comment will be remembered as his "deplorables" moment.
More important, a Youngkin victory would show that the educational fights that have mostly been playing out at the local level can have an impact at the state and perhaps the national level.
Education has loomed large in the suburbs. The suburban areas around Washington, Richmond and Virginia Beach have swung hard to the Democrats in recent years. And the larger Trump electoral trade-off of gaining working-class voters and repelling people in the suburbs worked for him once nationally, in 2016, but has its limits.
Youngkin's approach has been to give suburban voters a "permission slip" to support him, by making himself broadly acceptable through his biography and demeanor. On top of this, he's associated himself with the suburban revolt against school boards, most famously in Loudoun County, and talked up a cost-of-living-oriented economic agenda.
It's been easier for Youngkin to forge his own path in a state-level race, where the right Republican candidates can overcome blue electorates. But if he wins, it will show that at least some of the terrain Democrats picked up during the Trump years can be clawed back, that the GOP needn't yoke itself mindlessly to Trump's vulnerabilities and that the midterms next year look particularly bleak for the Democrats.
Yes, they should fear the fleece.