Justin’s Guide: Master the Art of Rocking a Baseball Cap

JOHN MILLER
7 Min Read

I came of age during a time when sporting a baseball cap in somewhat formal situations was considered as inappropriate as going to a funeral dressed in Bermuda shorts.

It’s not true anymore.Caps are now making waves at office gatherings,red carpet events,and cocktail parties.They’re also welcomed at the White House.

The style of the MAGA Republicans is copied from urban American culture,” stated Houston White Jr., a Minneapolis-based designer and entrepreneur, as he sat in the barbershop within his Camdentown Flats development. This space also houses a café and residential units. “It’s something they took from us.

White presented a compelling case that ’80s figures such as Ice Cube and Russell Simmons played a key role in initiating this trend by always remembering their roots.

It’s just a reflection of growing up as a Black guy from the neighborhood,” explained White, who was seated next to “The Autobiography of Malcolm X” written by Alex Haley and Jay-Z’s “The Blueprint” album. “How can I carry that essence along? That’s why you might see me wearing a cap with my suit or blazer.

When questioned about who deserved a place on the Mount Rushmore of cap legends, White along with his collaborators Ron Richard and Tim Sullivan became quite enthusiastic. Director Spike Lee was an easy inclusion for them. They also agreed that musician-actress Teyana Taylor should be part of this group. Other notable figures like Chance the Rapper, Janelle Monáe, Eva Longoria, and Denzel Washington were strong candidates as well.

Next, we have celebrities exerting excessive effort.

Tiger Woods appears uncool with his cap positioned backwards,” stated White, who shares an enthusiasm for hats similar to his passion for golf. “It’s clear when someone isn’t genuinely into hats and is merely sporting a costume.

The group recommends that everyone over 35 opt for dad caps featuring adjustable straps at the rear and rounder rims. Avoid

think

About wearing it backward. Attempting to resemble Will Smith from his ” Fresh Prince” era is a futile effort.

It’s akin to your grandmother sporting a miniskirt,” remarked Richard, a business consultant. “You’re basically seeking attention.

The partners think that both Musk and Trump make a style mistake by wearing hats that attempt to fit the entire slogan “Make America Great Again” instead of simply using MAGA.

They’re attempting to wear a billboard, which requires ample space,” explained White, who emphatically advises beginners to test numerous styles before finalizing their choice. “These hats simply don’t sit well on their heads.

Local fashion consultant Chanelle Whimper is more lenient.

Remove the political aspect from it. I’m not upset about the appearance,” stated Whimper, who is well-known in the Twin Cities fashion community as the FlyGirl. “When Trump pairs it with a suit, it garners significant notice. It’s all about adding an edge to your style.

She thinks that even us regular people have a good chance of getting away with quite a bit if we put effort into matching our hats with other clothing items, such as shoes or denim.

“If you concentrate on the overall appearance, the chances of appearing ridiculous are quite slim,” she stated.

Whimper, having provided consultation for Nordstrom, embraces risk-taking much like her cultural icon Erykah Badu. This influence is evident throughout her St. Paul home with numerous references to Badu visible everywhere.

Nearly all of his 100 hats feature bright colors and snapbacks adorned with Lisa Simpson, Teletubbies, and Saturn pins and patches. This eclectic assortment, which also comprises many bunny ear headpieces and beanies, is so varied and quirky that even his mother and 15-year-old son often borrow items from it.

I prefer not to conform to a standard image where everyone looks alike at work,” explained Whimper, showcasing her elongated acrylic nails in vibrant, multi-colored hues. “It’s not about drawing everybody’s focus towards me whenever I enter a space; rather, I enjoy expressing myself through distinctive styles such as wearing an unusual hat.

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.

Certainly, you could opt for a more budget-friendly approach. Both Houston and Richard were enthusiastic about the new caps they recently purchased from Target.

For those willing to splurge, MartinPatrick3 is worth exploring; starting from May, Whimper will be involved here. This high-end apparel shop in downtown Minneapolis offers exquisitely made caps priced at $135 each. However, one doesn’t have to search far to discover hats for less than $30 adorned with classic designs such as Jack Daniel’s, Hamm’s Beer, and Ace Hardware logos.

This may appear expensive for an item you typically wear only during Twins games and when mowing your lawn. However, it becomes more justifiable when compared to what you shell out for other fashion items such as ties and handbags.

A hat serves as the seasoning of attire,” White stated. “Billionaire tech moguls such as Mark Zuckerberg typically keep their style simple, which appears normal and reasonable. However, expecting the employee working under these tech tycoons to adhere to a specific dress code? That’s absurd.


©2025 The Minnesota Star Tribune. Visit startribune.com. Distributed by Tribune Content Agency, LLC

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I am a journalist with a passion for delivering clear, accurate, and engaging news. Every day, I cover a range of topics—from national affairs to global developments—ensuring that readers stay informed with trustworthy reporting. My work includes conducting interviews, verifying facts, and crafting stories that matter. As a contributor to Burnsvet.com, I strive to uphold high editorial standards while making complex issues easy to understand. I’m proud to be part of a platform that values truth, transparency, and real-time reporting in today’s fast-paced media landscape.
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