Part of the appeal of the clothes are the casual, classic styles with soft comfortable and even pretty fabrics (yes, even for the men) that look slightly aged but feel good to the touch. Even the brand's visual identity with its cursive style wordmark is slightly pretty—and dare we say—feminine. Home décor items are nothing particularly ground breaking with perhaps the sole exception of a martini lamp complete with olive and thatched umbrella as the shade.

The "good life," of course, has its price. Most single clothing items retail in the US$ 100 range per piece, with lesser expensive items (such as a simple women's knit tank top) hovering around $ 50.

To reflect its clientele and aspirational lifestyle, retail locations are reported as selected based on upscale destination resort communities such as Newport Beach, California, Scottsdale, Arizona, and Maui, Hawaii, in locations that invite leisurely "strolling" versus the suburban mall. The brand has also sponsored the 2004 Newport to Ensenada Yacht Race and PGA—events that highly complement the brand's positioning. Tommy's parent company, Oxford Industries, has other golf brands in its portfolio as well.

Unlike the stark, controlled feel of Banana Republic, retail interiors echo a dreamy island lifestyle with lots of wide space on the "old family plantation." Plenty of rattan, light colored, slightly aged paint and the tea-stained wallpaper look that Ralph Lauren perfected is featured throughout the store.

It is actually Ralph Lauren who Tommy Bahama comes closest to positioning-wise. Simple, classic clothes for both sexes made with finer fabrics, both leveraging the idea of a comfortable casual, slightly worn life—only one is town and country and the other is sun and surf. The only thing Mr. Bahama doesn't do is couture. Of course, Mr. Lauren doesn't do umbrella drinks and appetizers either.

Started in 1992, Tommy Bahama founders Tony Margolis, Lucio Dalla Gasperina and Bob Emfield manufactured and wholesaled clothing for premium department stores such as Nordstrom's, Saks Fifth Avenue and Neiman-Marcus before opening their first branded retail store in Naples, Florida, four years later.

While clothing and dining may seem like the fruit of innovative strategy concocted behind closed meeting doors, the restaurant concept apparently was the result of the Naples' location landlord's suggestion to take additional space to open a restaurant with the retail store. Hence, Tommy Bahama's Tropical Café was born complete with fine dining under thatched umbrellas—an opportunity to extend the good life.

Alycia de Mesa is a brand identity consultant and writer with over 10 years experience from Fortune 100 to start-up companies. She is author of Before The Brand, the definitive brand identity handbook, published by McGraw-Hill (under the name Alycia Perry).