Justin: How to rock a baseball cap

I grew up in a generation in which wearing a baseball cap in even semiformal settings was as rude as attending a funeral in Bermuda shorts.

That’s no longer the case. Caps are making a splash at office meetings, red carpets and cocktail parties. They’re even accepted at the White House.

“The look of the MAGA Republican is borrowed from urban America,” said Minneapolis designer and entrepreneur Houston White Jr., sitting in the barbershop of his Camdentown Flats complex, which also includes a coffee shop and housing units. “They got that from us.”

White was making a convincing argument that ‘80s icons like Ice Cube and Russell Simmons helped kick-start the trend by never forgetting where they came from.

“It’s part of being a Black boy from the block,” said White, sitting near the book “The Autobiography of Malcolm X” by Alex Haley and Jay-Z’s “The Blueprint” album. “How do I bring a part of that with me? So I wear a cap with a suit or blazer.”

White and his business partners Ron Richard and Tim Sullivan got animated when asked who belonged on the Mount Rushmore of cap legends. Director Spike Lee easily made the list. So did musician/actor Teyana Taylor. Chance the Rapper, Janelle Monáe, Eva Longoria and Denzel Washington were all contenders.

Then there are celebrities trying way too hard.

“Tiger Woods looks terrible with his hat laid back, because Tiger Woods is not cool,” said White, whose obsession with caps lines up with his love for golf. ”You can tell when you ain’t really a hat person and you’re just wearing a costume.“

The trio advises anyone over 35 to stick with dad caps with straps in back and rounder brims. Don’t even think about wearing it backwards. Trying to look like Will Smith in his “Fresh Prince” days is a fool’s errand.

“It’s like your grandma wearing a mini dress,” said Richard, a business consultant. “You’re just searching for attention.”

The partners believe Musk and Trump commit a fashion faux pas when they wear caps that try to squeeze in all of the slogan, “Make America Great Again” rather than sticking with MAGA.

“They’re trying to wear a billboard, which needs a lot of room,” said White, who strongly urges newbies to try on lots of different models before settling on a look. “The caps don’t fit their heads.”

Local stylist Chanelle Whimper is more forgiving.

“Take the politics out of it. I’m not mad at the look,” said Whimper, best known in Twin Cities fashion circles as the FlyGirl. “Trump draws a lot of attention when he wears it with a suit. It’s being a little edgy with your look.”

She believes even we ordinary folks can get away with a lot if we take the time to color-coordinate our caps with other attire, like shoes or jeans.

“If you focus on the whole look, the odds of you looking silly are pretty low,” she said.

Whimper, who has consulted at Nordstrom, is all about taking chances, just like her pop culture idol Erykah Badu, whose image pops up all over her St. Paul apartment.

Her nearly 100 hats favor loud colors and snapbacks with pins and patches of Lisa Simpson, Teletubbies and Saturn. The collection, which also includes lots of rabbit ears and beanies, is so diverse and funky that both her mom and 15-year-old son borrow from it.

“I don’t want to have to fit in a box where you have to look like everyone else in the office,” said Whimper, sporting long acrylic, multicolored fingernails. “ Not that I want everyone to pay attention to me when I’m in a room, but I do like to have my unique look and sometimes a hat will do that.”

One of her prized possessions, a plaid cap nodding to the fictional McDowell’s fast-food chain in “Coming to America,” is so new she hasn’t even worn it out yet. The new hat cost her $60, a bargain compared with the $200 she recently spent for a customized collaboration between Denim Tears and New Era.

Of course, you can get away with spending a lot less. Both Houston and Richard raved about new caps they just got at Target.

Those with money to burn should check out MartinPatrick3, where Whimper will start working in May. The upscale clothing store in downtown Minneapolis sells $135 meticulously crafted caps. But you don’t have to look very hard to find hats under $30 with vintage logos of Jack Daniel’s, Hamm’s Beer and Ace Hardware.

That might still seem like a lot for something you’re accustomed to slipping on only for Twins games and mowing the lawn. But it’s reasonable when you consider how much you spend on other fashion accessories like ties and purses.

“A hat is like salt. It’s flavor,” White said. “Those billionaire tech bros like Mark Zuckerberg don’t dress up and that seems natural and expected. But the guy working for the tech bro is expected to dress a certain part? That’s ridiculous.”