California Cowboy’s High Water shirt

Drew Clark has a thing for design and merchandising.

The founder of San Francisco-based apparel line California Cowboy has clocked time most recently as vice president and head of merchandising at the men’s made-to-measure shirting company Trumaker. Before that, he was director of merchandising for U.S. outlet stores at Levi Strauss & Co. among other positions held at the denim firm, along with senior merchandising positions at Old Navy.

In November Clark struck out on his own to start California Cowboy, which manufactures within the state, and raised nearly $40,000 in an Indiegogo campaign that closed in May. The total was about double the goal the company originally set for itself.

California Cowboy on Monday will hold,its first pop-up in Los Angeles as part of a pool party event involving dating site Three Day Rule and social networking group The Ivy Plus Society at the Viceroy in Santa Monica. That’s ahead of much larger plans to launch the brand into more real-life activities and at retail.

The company, which began fulfilling e-commerce orders through its site in July, counts the High Water shirt for men as its hero product at $135. The terry cloth-lined shirts come with a zippered waterproof pocket for a phone and a bottle opener that can sit in an interior pocket of the shirt. California Cowboy also has T-shirts that start at $34. Fall will see the introduction of more fleece with items in the range of $80 to $150. Bottoms will likely be rolled out next year.

The thoughtful elements, such as the pockets or the shirt prints, are aimed at being conversation starters, said Clark, who is bent on using his brand to get more people off their phones and into the real world to interact with one another.

“One of the things that I really like about style and apparel is you can actually leverage it  to create conversations with people,” he said.

The company is putting the finishing touches on a Land Rover Defender 90 that’s been outfitted with a modular unit made of reclaimed wood. It pulls out from the vehicle, which will be used as a traveling store. California Cowboy is currently in talks to bring the Land Rover to different events following the upcoming Santa Monica pop-up, with a longer term vision that calls for a fleet of vintage cars to make the brand mobile.

“My background is in brick-and-mortar retail and I think it’s a really important part of the shopping experience,” Clark said. “For the fabrics and the style that we’re developing, it’s a little bit harder to communicate that over e-commerce.”

A mobile fleet is also an opportunity to be resourceful by also using the roving vehicles as the basis for creating digital content, Clark added.

The fleet would complement flagships, with California Cowboy already having executed a letter of intent for what will be its first store in San Francisco.

The company, Clark said, is also in talks with potential retail partners – which he declined to name other than to say those channels will sit within the boutique and e-commerce spaces.