How Dale Built His Airbrush Business with OTTO CAP® 39-165 Trucker Hats

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How Dale "The Airbrush Guy" Jackowski Built His Business Around OTTO CAP®'s World-Famous 39-165 Trucker Hat

Some artists use canvas. Some use walls.

Dale Jackowski?

He prefers foam-front trucker hats. Not just any foam trucker though. We’re talking about the OTTO CAP® 39-165, which is the undisputed MVP of custom headwear in Dale’s shop.

This isn’t just a story about paint and hats. It’s about finding that one tool that fits just right (like a glove, if gloves went on your head that is) and running with it.

From Richmond Streets to Social Feeds

Dale “The Airbrush Guy” Jackowski didn’t fall into the art world by accident. Since 2010, he’s been slinging color all over shirts, hoodies, murals, and yes, a lot of hats.

His home base is in Richmond in the great state of Virginia, but thanks to social media and a little word-of-mouth buzz, his work has traveled a lot further than his paint-splattered shop walls.

You’ll find him on Instagram and TikTok under
@Dale_The_Airbrush_Guy, where you’ll see him pulling off live airbrush sessions that rack up millions of views.

And the product that keeps all this rolling? The one he stocks by the truckload? OTTO CAP®’s 39-165 Trucker Hat.

So, Why The 39-165 Hat?

Like a lot of great things, Dale found OTTO CAP® hats the old-school way through another artist who pulled him aside and said, “Hey, try these.”

That was over 15 years ago. He ordered a few blanks, ran some tests, and the rest is airbrushed history.

He’s tried others. Hats with crooked crowns, flimsy fronts, mystery stitching. Not fun when you’re painting live at a party and your surface is folding like a cheap lawn chair.

But OTTO CAP®? Every single 39-165 comes in like a champ.

Built to Be Painted

The magic of the 39-165 is in the details. Sturdy crown structure. Consistent panel shape. A foam front that drinks up color without bleeding or warping.

“They take paint beautifully,” Dale says, and that’s the kind of review you trust when it’s coming from someone who’s airbrushed thousands of them.

Consistency isn’t just ‘a nice to have. In Dale’s world, it’s non-negotiable!

The Hat Hustle

Every hat is airbrushed live at events or on TikTok.

Specifically, he pops out a hat and aims his airbrush, and then he brings bold lettering or full-blown characters to life in minutes.

He averages thirty custom hats per hour at events. That’s a new masterpiece in about every two minutes! And yes, it’s just as fun to watch as it sounds.

The OTTO CAP® 39-165 is his go-to for those moments.

“It’s fast to paint, fun to wear, and affordable enough for events,” Dale says.

And it always looks sharp (especially in video, where the clean lines and bright contrasts make every post pop).

Color Theory Meets Real-World Sales

Dale keeps a rainbow of hats on hand, from wild neons to pink-and-teal combos.

But the one he always has to reorder? Black and white.

That’s because this classic combo does everything he needs. It’s neutral enough for any design, but it’s also bold enough to stop people mid-scroll. It shows off the paint, it photographs like a dream, and it wears well on just about everyone. Black and white is the silent hero of his airbrush empire.

Big Numbers, Big Impact

This Isn’t Just a Hobby…

Over the years, Dale has sold thousands of custom OTTO CAP® trucker hats. And that’s not counting the ones that show up in videos or live streams just for the buzz. His custom hat content has millions of combined views, and those numbers convert into real orders too.

Repeat customers aren’t shy about their feedback either. They love the fit. They love the look. They love that it holds up even after getting sweat-soaked at a festival or tossed around in a backpack.

In all of Dale’s years doing this? Not a single complaint about the hat’s quality.

Trade Secrets from a Hat Whisperer

Tips for New Artists

Dale’s got advice for anyone eyeing the airbrush life:

First, he says, know your surface. Foam-front hats can be forgiving, but only if you understand their shape. That gentle curve can make or break a design, and especially for when you’re blending colors or working in tight detail. Don’t be afraid to mess up. Just respect the material.

Second, keep your strokes bold. Timid airbrush strokes are like nervous handwriting; shaky, uneven, forgettable. Confidence shows up in the art.

And lastly, invest in a mannequin head. Seriously. Being able to rotate the hat like a rotisserie chicken while painting makes everything easier (especially when you’re going in with fine lines or trying to wrap a design around the curve).

Don’t Overthink It

Dale’s style is bold, urban, and fast. That’s part of the appeal because it doesn’t feel overworked. It feels alive.

“Less is more,” he says, and he means it.

Don’t layer on detail until it chokes the design. Let the color breathe. Let the lines do the talking.

Why It Works (And Why It'll Keep Working)

Some folks build businesses on spreadsheets. But not Dale.

The OTTO CAP® 39-165 didn’t just survive the test of time. It helped launch a small business into something way bigger. It’s more than a blank canvas. It’s the frame, the foundation, and the secret weapon all at the same time.

And as Dale puts it best:

“OTTO CAP®’s trucker hats are by far my (and my customer’s) favorite item to customize. They’re perfect for airbrush artwork and I enjoy redefining what that looks like in the modern age.”

Turns out, when you find the right hat, you don’t just wear it.

You build a legacy on it.

Connect with Dale on social media to discover more!

IG and TikTok: @dale_the_airbrush_guy