Doug Wood has spent 25 years building Tommy Bahama into a brand recognized well beyond golf courses and beach resorts. He also says he can tell, almost on sight, where a customer is from.
“Typically, you can tell East Coast, West Coast really fast,” Wood told Fortune in a long ranging and rather hilarious conversation riddled with nuggets of fashion advice—and some of fashion’s hottest takes. Right now, he said, that means spotting a very specific look.
“The East Coast is going through a massive preppy phase. Ralph Lauren is riding it high, and it comes off very much East Coast.” He’s not entirely sold on the trend himself. “That’s not my favorite phase,” he said. “I like the floral phase. It’ll come back.”
For the CEO of a company whose entire brand is defined by its floral phase, his comments may not be that surprising. After all, it was Wood himself who brought up how ubiquitous Tommy Bahama shirts are (“whether it’s Danny DeVito or you know, we made it into the The Simpsons Movie“) and also how his brand is the epitome of all shirts of a similar style regardless of the manufacturer.
“There are so many apparel brands out in this world that aren’t known for anything, and we’re known for a loud Hawaiian shirt,” Wood said. “And you know, it used to be a big part of our business. Now it’s not that big part of our business. But I don’t care whose shirt it is.”
The shirt style, whether it’s The Gang wearing many in Always Sunny to it being a memento from a love lorn in Forgetting Sarah Marshall (“I admire Sir Tommy Bahama an awful lot,” as uttered by the character Aldous Snow, played by Russell Brand in the film), is a testament to a level of cultural recognition most apparel brands can never reach.
It’s recognizable enough that writers can drop the name in without explanation, and secure enough that Wood treats each reference as free publicity rather than a threat to the brand’s image. As he put it: “There’s no such thing as bad PR.”
“They call it a time bomb shirt, and I’m always like, ‘yeah, hey, I got the call out,'” he said. “It’s amazing, the movies, the TV shows, the callouts, but it’s because it’s something that everybody knows, and people love to just kind of pull it into the joke because it makes it, you know, more real.”
The fashion map of the United States, according to Doug Wood
The East Coast and West Coast (dubbed “Beast Coast” and “Best Coast,” respectively, for those who have some skin in the game but ultimately don’t talk about much else than geographical cultural differences) have never agreed on much.
New York gave the world Wall Street suits and subway commutes; Los Angeles gave it hoodie-clad tech founders and cars for everything. Boston built its identity on blue-collar grit and a Celtics chip on its shoulder; LA built Showtime Lakers glamour. New York does deep bagels and bodega coffee; the West Coast invented the whole third-wave, oat-milk-latte pipeline. Even the comedy split down coastal lines: SNL’s live-wire New York energy against the polished, studio-built sensibility of LA sitcoms. And decades before any of that, the coasts fought their most famous battle in hip-hop, Bad Boy’s New York grit against Death Row’s LA gloss, a rivalry serious enough to end in tragedy.
It turns out the divide runs just as deep in a much smaller decision: what you throw on before you leave the house. Wood says he can spot the difference in seconds, from the just cuts of shorts to the colors people mix without thinking twice, and that the geography shows up on a customer as clearly as it does anywhere else in American culture.
In fact, the regional divide shows up in ways Wood said the company has to actively manage, not just notice. “I laugh at some of the combinations of colors between shorts and pants that you would never see in California,” he said. Getting the assortment wrong in either direction is a real business problem, he said, describing his own reaction to seeing the wrong regional mix on a store visit: “I’ll walk into a California store and I’ll say, look, what the hell, I’m not in Florida, this feels like Florida to me.”
Not that Florida style is inherently “wrong” or better or worse than any other—it just doesn’t belong in California, just how Tommy Bahama will carry more appropriate clothing in its East Coast stores over those on the west. Part of this isn’t a Tommy Bahama issue, but, Wood said, obvious for all brands as they stock up their brick and mortars.
“We have brands who are super strong in the Southeast that nobody on the West Coast is going to get caught dead in,” Wood said, adding certain labels are strong in one region and absent from another, and it’s obvious the moment he spots someone wearing them out of place.
“When you see that product, you go, ‘I wonder if she knows how much she’s standing out right now,'” he said.
The read isn’t limited to geography. Wood was asked about a golf outing where a friend’s father showed up in a traditional dress code, only to find the rest of the group in quarter-zips and in vests from a brand that shall go unnamed but is synonymous with New York’s Wall Street. Wood didn’t dispute that change, adding he tracks those changes closely, down to the specific brands and silhouettes moving through a region at any given moment, whether that’s a country club or a neighborhood bar.
“It’s part of what we do,” he said of watching those shifts unfold, describing it as something the company has to stay on top of just to keep its own assortment right.
‘Don’t wear that’
Wood was happy to poke fun at himself and his own fashion sense—or lack thereof before he met his wife. At this point in the almost delirious conversation that had more quips and one-liners than an Ace Ventura movie (itself complete with an assortment of Tommy Bahama shirts), Wood was asked about younger men meeting their girlfriend’s parents for the first time and wearing their cleanest athleisure polo shirt.
“Oh God. You know, first of all, that was probably me. Oh my God,” he said. “My wife still checks me out about that type of thing.”
But that mistake is due to a knowledge gap, rather than a character flaw.
“I think fashion is something that not everybody is raised with,” he said. “I bring up my wife because she absolutely had to train me. Thank God she has taste, and so I think that it’s just a matter of people not understanding.”
“Don’t do that. You know, don’t wear that.” His prescription: time, experience, or someone willing to say something. “It’s always good to have a friend, or a friend whose mom works in retail, and you can go say, help me, I’m going on a big date.”
Wood said some people don’t need the help.
“There are people out there that look good in everything. They can pull off an Under Armour shirt and make it look fashionable,” he said. “And then there’s people like me. I better have something that makes me look good, because this isn’t natural. This isn’t going to happen.”
He credited his own design team with a similar instinct.
“It’s amazing how they can pull things together and do things you wouldn’t put together yourself, and man, does it work,” he said. “That’s talent.”
Part of that goes back to the demographic of who purchases Tommy Bahama clothing. He disclosed that denim and bottom is a big chunk of the brand’s sales (“My third-best item in men’s right now is denim. I sell a ton of denim. Nobody thinks of us as a denim company. You know, 30% of our business is bottoms”). And part of that is also being willing to laugh at the version of Tommy Bahama the culture has run with.
He brought up an old internal joke about the company’s own men’s swim line: “We sold men’s swim, but our swim never got in the water, so our guy didn’t swim. Our guy just laid around the pool and drank martinis.” He said that image, while funny, never matched what the brand actually made.
“Nothing could be further from the truth about men’s sportswear,” he said. “Now you better have performance something in that product. It better breathe, it better wick.”
Even so, he said the company hasn’t let go of where it started.
“I’ve got the company started with a men’s floral silk shirt, and I still have a guest who’s just so freaking loyal to that shirt,” Wood said. “If you’re looking for one, I promise you I’m going to have one, and I promise you it’s going to be the best one you can find.” That loyalty, he said, is part of why the brand can afford to be in on its own joke. “That relaxed, fun island lifestyle transcends,” he said. “It’s a state of mind.”
