The Bailey Hat Company’s Chuck Bailey was a Western original.
The cowboy hat remains an iconic piece of Americana. Wear one anywhere in the world today and you’re either a Western hero—or a target. The West has always been about fascinating and significant people and is still a place where a handshake can mean as much as a notarized piece of paper. That’s something to not only admire but also to which to aspire. One person who met and exceeded such honorable behavior was Chuck Bailey (1924–2013). Many may not recognize the name but most in the West would recognize the brand of hats that Chuck’s last name represented.
Back in the pre-Internet 1990s, the Bailey Hat Company was using mostly print imagery to sell its headwear under the watchful eye of its namesake owner. Bailey Hats had long been a standard in the industry back to when Chuck’s father, George, started the business in Los Angeles in 1922, initially called the Pacific Harvest Hat Company before allowing the company to take his name.
George S. Bailey saw the emerging need to create a hat company that not only catered to the region’s dress hat market, but one that also served the growing national Western wear market. He was an authentic hat man and quickly recognized Hollywood’s leading men as global arbiters of taste and style. He dedicated his life to providing them with fine quality hats—or as he called it, luxury styling.
In the 1920s, L.A.’s film business accounted for nearly one-fifth of California’s annual manufacturing business, and while Bailey worked with the studios, he also catered directly to the needs of Southern California ranchers, businessmen, oil tycoons and the newest segment of the population, movie stars, with what Bailey’s billboards described at the time as the “best hat possible.”
George’s son, Chuck, worked in the factory as a schoolboy and later took over his father’s business, running the company until his retirement and sale of the company in 1994.
I met Chuck Bailey back in the 1980s when I was running a small advertising agency and had been introduced through the agency’s founder. I had traveled to his factory in the far end of L.A’s San Fernando Valley, through some pretty dicey looking parts of town until passing through a chain link gate topped off with some impressive ribbon wire. As I parked in the lot, looking around at all that concertina wire I thought, “all this for a hat factory?”
When I stepped inside, I got my answer. On the entry wall was a little sign that said simply, “Safety First,” and was then whisked away on a tour of the factory. It didn’t take long for me to see just how unique this handcrafted item of apparel really was. It took 13 steps, all by hand, to build a hat—cowboy or otherwise. From the first forming of the fir hat body to the ultimate finishing, this was a business of craftsmen and care—an artisanal skill that endures today.
When I entered his modest office, I was introduced to Charles Bailey, a man with a smile as big as Southern California. “Call me Chuck,” he urged with a grin. It was something I would hear him say hundreds of times. That was the summer of 1986, and for almost a decade I worked with one of the finest men in the hat business.
Charles “Chuck” Bailey was a giver as was his beloved wife, Gwen, whom he had met while she was in nursing school. They fell in love and married in 1951 and spent a lifetime together helping everyone that needed it. As Chuck told me on many occasions, one of his life’s greatest joys began when he married Gwen, and the two of them participated in countless volunteer and charitable organizations.
Chuck had an incredible way about him that always put people at ease—whether it was his smile or his earnestness to listen, he was always in the moment with whomever he was with. He had an uncanny knack of disarming anyone by showing them his ever-present cowboy hat and saying, “Here, try this on, you won’t believe how great you’ll look!” Hats were his calling cards, and kindness was his chief sales tool. Nothing made him happier than to see someone try on a hat.
And it is true, as I have seen it myself many times—put on a cowboy hat that truly fits and suits you, and suddenly you are changed for the better. I still can’t figure it out, but it’s true. After the birth of my oldest daughter, one of the first things that showed up at the house was a hat box from the Bailey Hat Company carrying a little size 6, cowboy hat with the name “Laura Reynolds” stamped in gold on the sweatband. Five years later, a hat showed up for my second daughter’s birth. Size 6.
During the early 1990s the hat business was booming, supported in large part by the recent cultural success of the impressive television mini-series Lonesome Dove in 1989. The authentic West was something that was important to Bailey Hats and they used authentic, low key imagery that was sprinkled with “appropriate” celebrities like Clint Black and Ian Tyson. One of the popular illustrators of the high-desert West was a quiet young man named Larry Bute who had lived the life he depicted in his artwork. Larry created a number of memorable pieces for Bailey through the years. Chuck Bailey loved authentic, quality people.
Our greatest blessings are the memorable people that come into our lives and broaden our view of humanity. Chuck Bailey was one of those significant ones that appeared in my life and so many others. Chuck passed a way in 2013 at his home in Oregon at the age of 89 where he and Gwen had moved after the hat company sold. His beloved Gwen had died just two months earlier and he probably figured he needed to catch up with her, as she headed on up the trail ahead of him. One can only imagine Chuck Bailey introducing himself to folks along the way and showing them his hat, “Call me Chuck.”