Having grown up playing baseball in the summer heat, Tommy Breeze was certainly no stranger to hats.
“I’ve been wearing hats since I was a very little kid,” the Fairfax native remembers. “But for a long time, I would just wear hats while I was playing baseball.
“Then something switched.”
And how.
These days, hats are a huge part of Tommy Breeze’s life. In fact, they’re what he’s known for – as a successful designer of his own eponymous line of trucker, snapback, soft top and other hats, caps and beanies that have been worn by Lady Gaga and other notable personalities.
But what switched to take him from an occasional hat wearing, baseball-loving kid to pursuing a career in hat couture?
“I actually started wearing hats because I was always self-conscious about how my hair looked without a hat on,” says Breeze, who really got into headwear during his days at Whitman College in Walla Walla, Washington. “I was like, ‘it’s going in every direction.’ And then I was like, ‘Just put a hat on and it kind of gets everything in order.”
Tommy Breeze, owner of Tommy Breeze Company, shows some of the hats he designed at his studio in Fairfax, Calif., on Friday, May 30, 2025. (Ray Chavez/Bay Area News Group)
Yet, controlling the messy hair was really just one of the reasons that deepened his appreciation for hats, and how they dress your head for comfort, fashion and almost any kind of weather. He also came across a few really special hats that become so very near and dear to his heart.
The first was found at a thrift store in Walla Walla and Breeze — yes, that’s his real last name — just loved how it not only hid his self-described “weird” hair but also accentuated his personal fashion.
The second was a corduroy cap that he got during a giveaway promotion at a San Francisco Giants game.
“It fit me so perfectly,” Breeze says of the beloved freebee. “The hat just really spoke to me.”
Then a friend borrowed that Giants lid and, for a while, Breeze was left without his favorite way to hide his hair. And that brought him to the realization that finding a good hat – the right hat for a specific individual – can actually be a tricky proposition.
“Back then it seemed difficult to find an awesome hat,” he says. “Like, ‘How do you track down the perfect hat for you? Where do you even start with that?’ You don’t even know, as a person out there, what your options are.”
So, he decided to design and make his own hat – just for himself. At the time, he had been doing small paintings – usually of cypress trees – and then putting them onto small buttons to wear. So, the goal was just to take a similar design and transfer it to a patch that could then be placed on a hat – again, just for himself.
“I just wanted one hat — that was it,” Breeze says. “But I realized that when you’re ordering patches, you pretty much have to order 50 or 100 from the factory. Because they aren’t going to make a one-off for you. And, if they did, it would cost several hundred dollars.”
Tommy Breeze, owner of Tommy Breeze Company, shows some of the best-selling patches they sew on the hats he designed at his studio in Fairfax, Calif., on Friday, May 30, 2025. (Ray Chavez/Bay Area News Group)
He went ahead and ordered 50 patches – but the manufacturer ended up sending 100. So, he took the excess and decided to make a bunch of hats – hand-sewing his patches on pre-made hats – in the hopes of making back his initial investment.
It was a lot of work. But he loved it.
“Very quickly, it became obvious that I really enjoyed making the hats,” he says. “I really enjoyed stitching the patches on by hand. It was tough at first. There’s a steep learning curve. But I really enjoyed the activity of customizing hats. And my friends really dug them too. So, I just kept doing it.”
Starting out by posting just a half-dozen of his hats on Instagram in 2018, Breeze quickly saw demand grow. By the end of the first year, the aspiring hat kingpin had hand-stitched 1,000 lids.
These days, he’s doing at least that on a monthly basis, with annual sales for his Fairfax-based company heading toward 20,000 hats. He leads a team of sewists in creating a wide variety of hats, featuring a number of different California-inspired designs, which are sold at retailers around the Bay Area and beyond.
“We are still scaling,” Breeze says of the company’s growth over the years. “We’re still keeping it smaller, so we grow at the right pace.”
A list of retailers can be found on his website – tommybreeze.com — where hat lovers can also directly place orders themselves.
Tommy Breeze, owner of Tommy Breeze Company, sews a patch on a hat he designed at his studio in Fairfax, Calif., on Friday, May 30, 2025. (Ray Chavez/Bay Area News Group)
Tips for choosing the perfect hat, no matter your age or style:
Comfortable on your head: “That means looking at the crown shape,” Breeze says. “And also seeing what width and shape of brim is perfect for you.” That’s good advice, since – clearly – a comfortable hat is one you’ll want to wear more often.
Good fabric: “You also want to look for a hat that is premium quality,” Breeze says. “You want to have high quality fabric.” Like with any other article of clothing, a hat that utilizes high quality fabric will likely weather the years better.
The patch is it: “What really gets me excited is the patch design,” says Breeze, who started out in the business by hand-sewing the patches he designed onto hats.
Special connection: “It’s not a matter of any scientific approach, or any specific feature,” Breeze says. “It’s about making your own connection with your own hat. And finding that love that lives in that relationship between you and what you wear. …Maybe it’s because you love the fit of the hat. Maybe your favorite thing is the patch and how it speaks to you and how it helps you channel your happy places in the outdoors.”
Taking ownership: “If you purchased a hat from me, it’s not my hat anymore — it’s your hat now,” he says. “It is a Tommy Breeze hat — yes. But more importantly, it’s your hat.” And wear it as such.