Tom Tiffany went to Milwaukee’s Summerfest, and, well, his festival garb kind of screamed of, “how to reveal you’ve never gone to Summerfest without revealing you’ve never gone to Summerfest.” Someone should tell Tom that there’s a literal dress code for male Summerfest fashion; I mean there have even been television segments about this.

Male Summerfest fashion starts with khaki shorts with pockets and a weirdly patterned shirt, not blue jeans and a staid buttoned-down, long-sleeved dress shirt. I wrote on Facebook that he looked “hot,” and a few snarky reader comments later, I felt it was necessary to clarify that I was referring to the temperature. I stipulate that Tom Tiffany is not “hot.” But Wisconsin doesn’t elect hot governors, otherwise we’d have Gov. Kleefisch. We elected Tony Evers and Jim Doyle after all. I mean, c’mon. So this helps him.

And don’t even get me started on the Democrats, who are parading around in a colorful kaleidoscope of pastels, jumpsuits, weird rainbow shawls, and buttoned up purple polos. It makes my eyes hurt. And it strikes me that we have entered a new era of gubernatorial fashion as a result.

The Democrat Primary Pool Party

The Democrats look like they’re partying the day away at a pool party in San Francisco, but with a lot of LSD – they look weird, to varying degrees. All they need is a couple of big striped beach balls to bat around at their electoral version of the Phoenix Hotel, a dingy white van with a disco ball inside, and a few day drinks with little umbrellas. And lots of weed. It’s the Met Gala primary. Whatever, have fun. Just please for the love of God, keep your clothes ON. And don’t mess up our state because most of us really don’t want to abolish the MPD or Waukesha County Sheriff’s Department.

Some guy on Facebook sniped that it’s “vapid” to analyze gubernatorial fashion. But it actually matters. So let’s get serious for a minute.

Gubernatorial fashion choices are painting Tom Tiffany as the normal guy running against a bunch of college kids at a frat party. Who do you want crafting the state budget? Now, the latter might be a selling point in a primary dominated by youth and Dane County, but it’s hard to imagine anyone over 40 or north of Tomah seeing a woman in white painter’s coveralls (Fran Hong) as governor material. And I’m not even exaggerating. Maybe in her next TikTok, she will roll out from under a car on one of those creepers. Fun? Sure. Governor? No.

It’s why Tiffany has his best chance by far of defeating Hong. She just doesn’t give a flying f*ck, to borrow her favorite word, and it’s also going to be true of your tax bill, police, prisons, getting violent illegal immigrants out of the country, criminalizing grooming, boys in girls sports and more. That’s when it stops being funny. Anything goes? There’s a price for that. Norms exist for a reason, unless you want Wisconsin to become the Chaz. How did the summer of anarchic love work out for Portland and Seattle? People got a bunch of discarded syringes on their lawns, and the police decided the police-free Chaz (Capitol Hill Autonomous Zone) wasn’t safe because people were getting shot.

Does Political Fashion Matter?

You betcha! Ronald Reagan understood this, when he was dressed like a cowboy chopping wood on his ranch or holding a chainsaw in a shed (see below).

Political fashion can spectacularly backfire, of course. Hillary Clinton thought she was sending a signal by wearing a suffragist gender-gap-exploiting white suit. Kamala borrowed the 1990s power suit, and also lost almost all men, who saw her and envisioned Glenn Close boiling their family rabbit.

Michael Dukakis drives both a tank and the final nail into the coffin that is his election campaign. (1988) pic.twitter.com/u4FkcJXUDK

— crazy ass moments in american politics (@ampol_moment) March 24, 2022

Think Dukakis in the tank helmet or John Kerry in a hooded blue contamination suit (Robin Vos tried a version of that. Just like politicians should avoid eating corn dogs at fairs, they should probably stay entirely out of contamination suits.)

Donald Trump plays the fashion game well, with his red power tie and strategically unbuttoned suit jacket. It matches the machismo and the swagger, which is the image he’s after. Republican DA Eric Toney, who is running for Attorney General, gets this point, with his Glenn Youngkin style Navy vest with DA seal (and, since it’s summer, his Navy polo shirt with DA seal).

June in Wisconsin means breakfast on the farm! Hard-working family farms are the backbone of our state. Glad to celebrate agriculture in Walworth, Dane, and Manitowoc Counties this weekend. Thank you for everything you do! pic.twitter.com/Rte4eoJQZ4

— Eric Toney (@EricJToney) June 14, 2026

Approachable, pragmatic, consistent, and prosecutorial. Fits the job and the guy. I mean, he has a dog named Patton. An independent voter wrote me and said he wants to learn more about Toney because he had a firm handshake at a parade. “I’m sure he works on cars during the weekend,” he wrote, asking me for Toney’s bio. That’s a real quote.

The New Era in Gubernatorial Fashion

For years in Wisconsin, gubernatorial and political fashion has been, well, deadly dull and boring. I mean how many cheap blue suits with boring yellow ties can the public possibly endure. Mark Born and Tyler August aren’t exactly going to be tapped for the Paris fashion week runway. The lone exception is Republican Amanda Nedweski, who always looks like she’s heading to an attractive wine mom brunch in Delafield. Amanda, and Eric Brooks, settle down. It’s meant as a compliment. Really.

Evers is so boring that I can’t remember a single thing he’s worn, although he did post a photo the other day eating Kringle in a construction worker’s reflective vest (didn’t Trump do that first?)

Here’s why it matters in the governor’s race. How a candidate dresses creates an impression of the kind of governor they would be.

The State Dad

I’ve called Tiffany the State Dad, and his Summerfest pic reinforced this label. Even the creep who runs comms for Democrats, Philip Shulman, referred to Tiffany as the “state dad” the other day, so it’s starting to stick. I call Shulman a creep because he tried to score a political point using Sean Duffy’s adorable Down Syndrome kid the other day. That’s just despicable. But thanks Phil for helping further my State Dad concept.

I think voters want a governor who will be a steady rudder, and who won’t trash every norm we recognize. They want a Wisconsin-focused normal chief executive who won’t bring a lot of drama and who will make their lives better. That’s it. Evers was genius at this packaging. All he was missing was a daily video taking his shoes off and changing his sweater (c’mon, Britt, do better. You should have thought of that). Never mind that the Republicans in the legislature saved Evers from unleashing his inner crazy Bernie. People liked that he’s a seemingly harmless geek, or they wouldn’t have kept electing him. They trusted him to do no harm.

Trust. That’s what it’s all about.

Evers never looked crazy. He just didn’t. Goofy, sure. Crazy, no.

I went on Tiffany’s Facebook page the other day to find a picture of him with a cop for another story, and it was all photos of Tiffany looking like he just wandered out of a hay mow. As I’ve written before, though, this helps Tiffany forge a clear state identity whereas the Democrats want to attach him to Washington.

Looking like a State Dad whose wife better start shopping for him stat helps do this. He’s the normal one in the race who is focused on more important things.

I know guys like this. They own two pairs of jeans, two pairs of Khaki shorts, two sweatshirts and a bunch of T shirts, and they rotate them. That’s Wisconsin for you, where folks wear a sweatshirt to a nice dinner out. I trust guys like that because their priorities are in order. They’re too busy taking care of their families to worry about their eyebrows or color wheel. That kind of stuff only works on the coasts. Heck, my almost stepdad and hero Larry, the working class Dad, rotates three Carhartt sweatshirts, and when I asked what he wanted for Christmas, he said a Carhartt sweatshirt.

We don’t trust metrosexuals in this state outside of Madison and Brady Street. No man buns allowed! I think anyway. This election could be a test of that. But I wouldn’t bank on Wisconsin changing that much, so fast.

That’s why the political machine stuck metrosexual Republican congressional candidate Mike Alfonso in a flannel shirt for his direct mail up north and parked the Prius in the garage. His manicured eyebrows might cost him the primary, and I’m not kidding. I mean he’s trying to get votes from guys who live in deer hunting cabins in Winter (actual name of a town). You don’t want to look like an elite when you play construction worker.

It’s even more telling when the fashion choices scream inauthenticity, like leftist operative Rebecca Cooke prancing around a manure-filled farm in open-toed, backless sandals that would look better at a Kirk Bangstad (her former boss) beer tasting. This led her opponent, former Navy SEAL and flannel clad Derrick Van Orden to accuse her of being as authentic as a “Tijuana Rolex,” real quote. But since he’s a former Navy SEAL, he gets away with it.

Hey, I admit. I’m not a sartorial fashion plate either. I am not going to be tapped for the Paris runway either. I went into journalism, so I can’t afford Versace. But I’m not running for governor. I’m not dressing to send a political message.

In contrast, one can see the Democrats staking out their political turf through how they dress.

Tale of the Fashion Tape

A reader noted that the person who wins a political race is usually the person who “dresses the best.” I don’t think that’s true anymore on the left.

On the far hinterlands of the crazy left, you have anarchist supporting Fran “abolish the police” Hong, who praises the elections of people who think we caused 9/11 and who wiped their hand on an American flag. She thinks it’s great they won!

Hong’s gubernatorial fashion sense has captured the fancy of the young because it’s different. Never underestimate the appeal of a politician who promises something new and who doesn’t seem like one. It worked for Trump. He won because people are really frustrated with politicians and didn’t think he seemed like a typical one. Some of that is wearing off, but that explains his appeal.

So when Hong wears a stocking cap and deploys a cat burglar look on camera, this sends a message: “Hey, you disenfranchised, I’m not a regular politician. Vote for me, and we will blow things up together.”

That probably has limited general election appeal (do people really want to eliminate the U.S. Senate?), but Tiffany should not take it lightly. There’s a fine line, though, where strategically weird just becomes…weird.

How About the Rest of Them?

Mandela Barnes is also staking out his “I’m not your typical politician cred,” with his buttoned up purple and pink polo shirts and tats. There’s zero chance you will see Tom Tiffany in a purple polo shirt. And therein lies the difference.

I have to admit that Mandela is sending mixed messages. He’s showing off masculine tats and bulging pipes in feminine colors. I haven’t figured out what to make of that.

I pointed out that it’s lucky for the other candidates that the Democrat primary isn’t being determined by an arm wrestling match, which is just calling it like it is because it was kind of obvious. Although who knows, scrappy Hong might be able to take him. Brennan? No way.

But this throwaway remark made some people think I think Mandela is hot (my readers really need to get their minds out of the gutter.) I calmly explained that guys who think freeing killers is sexy and who lie on their resumes aren’t exactly my type, so nope.

Sara Rodriguez is going for the suburban soccer mom vote. We get it already. She’s the middle-aged mom who wears capri pants and sensible shoes to pick the kids up from basketball practice, ie she is trying to position as “the candidate who can appeal in Waukesha!” while ruthlessly being a pawn of the Democrat establishment, which is trying to kneecap Mandela and Fran behind the scenes. She’s trying to become the establishment choice, and she looks the part.

Pandering to utility companies kind of plays into that I guess, but wait – is there really a constituency for people who pander to utility companies? Sara has not endeared herself to Milwaukee’s historic black press, either. But she’s not going for that vote. She’s going for the vote of aging white liberals who frequent farmer’s markets in Wauwatosa.

This is the key to Tammy Baldwin’s electoral success despite her radical views. She runs around in Packer fleece jackets and blue jeans, not pink jumpsuits, and people think, oh, she’s not that crazy (until she votes.) She gets what I’m talking about here.

In contrast, David “I like some things Trump did!” Crowley and Joel “I ran Discovery World!” Brennan have adopted the basic suit-wearing corporate lawyer look. Which is probably why they’re stuck at 1 percent or whatever in a primary filled with “girls who just wanna have fun.” Too bad for their party, because that would probably work in a general.

Which brings me to my least favorite Dem, shrieking state Sen. Kelda Roys. (I’m told even other Democrats can’t stand her.)

Kelda Roys probably falls asleep with Mandela’s voter base dancing like sugar plums in her head. Isn’t it funny how white liberals pretend they’re the tolerant ones who are for diversity except when it comes to trying to stop the black and Asian candidates from getting ahead? The ally ship ends there. And I know for a fact that Kelda thinks her only hope is to wrestle away some of Barnes’ votes.

But…Roys is more likely to draw from Rodriguez, helping Barnes or Hong win the primary, ironically. It’s hard to see a revolutionary when you’re looking at a middle-aged suburbanish white woman in a cardigan and suit jacket, even when she yells about “abolishing ICE!” The Barb Lawton endorsement didn’t help.

Republican Andy Manske’s gubernatorial fashion screamed I just wandered in off the street from the local speedway. Take that!

So, yes. It actually does matter. It matters more where they all stand on the issues, obviously, but to some degree how they’re packaging themselves is a reflection of that. Tammy Baldwin camouflages her radical views with cautious window dressing; some of these Democrats are letting them all hang out.