Aloha shirts can be polarizing. They’re stylishly casual at cocktail parties, barbecues and in all forms of frivolity. But they’re also a fashion curse, particularly when not-so-well coordinated with multi-colored walking shorts and black socks.

Regardless, collared and short-sleeved aloha shirts, often called Hawaiian shirts, mostly exude an attitude of chill to the wearer and beholder.

President Harry S. Truman was featured on the cover of Life magazine in 1951 wearing a blue-and-white aloha shirt with two buttoned pockets. Ten years later, Elvis Presley, attired in a red-and-white patterned aloha shirt and a yellow lei, was the chosen design of his album Blue Hawaii. Actor Tom Selleck had his favorite Red Jungle Bird design shirt in the television program “Magnum P.I.” Musician Jimmy Buffett’s career is based on a carefree island lifestyle; aloha shirts are part of his signature attire.

“The fabric—some match the pockets, some don’t. The way the stitching is. Are they using a French seam inside?” says Aloha Sam of Captain’s Closet, the men’s clothing store in Naples. “There are copious amounts of Hawaiian shirt manufacturers. The best ones have those qualities.”

The ever-evolving style has been made for about 100 years. Nearly as many legends of the shirt’s origin are shared as the available colors, themes and alternative names—camp, cabana, cabin, lounge and vacation.

Vintage aloha shirt collectors know what they have. But yard-sale bargains still abound, as do $2,500 rarities on Etsy.

Tommy Bahama (picture above)

The original retail store and accompanying restaurant named after a fictitious character and conceived by three friends opened in 1996 in Naples.

The brand calls its wares “camp shirts,” and they’re available in about 200 brand stores and in many other retailers, including in Naples.

Tommy Bahama has expanded its clothing line, but its Hawaiian shirts made from 100% silk remain the merchandise flagship. 

“The market that we are in, Southwest Florida, is a very relaxed, casual kind of area,” says Aaron Marsh, manager of the Tommy Bahama store in Estero. “So the shirts that we have can transition from just being outside somewhere with a cocktail to dinner. It’s one of those things where you don’t have to go home and recharge your whole outfit.”

tommybahama.com

Hilo Hattie 

Hawaii’s largest manufacturer, retailer and wholesaler of gifts and apparel, including aloha shirts, is named after school teacher Clarissa “Clara” Haili. Education was fine, but singing and dancing were the educator’s passion, and she popularized the comedic style of hula.

Originally called Kaluna Hawaii Sportswear on Kauai, the company changed its name to honor Hilo Hattie in 1979. It was in honor of Haili, who changed her name in 1942, 10 years after the debut of hapa haole song “When Hilo Hattie Does the Hilo Hop.” Hattie died in 1979, and her namesake business was sold in 2008 to California company TOC Inc.

hilohattie.com

Kahala 

Marketed as Hawaii’s oldest apparel company, Kahala was founded in Honolulu by George Brangier and Nat Norfleet in 1936. All aloha shirts were then bespoke and cut from the Japanese silk used for making kimonos. Kahala changed the industry.

“Those at the top are all well-made,” says Aloha Sam, whose shirt brands include Kahala, Tori Richard and Paradise Found. “They use good buttons, good stitching, good fabrics. They’re unique.”

With silk rationed during World War II to make parachutes, Kahala opted for rayon. It felt like silk but was less expensive and readily available. Kahala’s popularity grew with its popular designs including canoes, coconut trees, fish, flowers, surfers and other Hawaiian motifs.

kahala.com

Reyn Spooner  

Reynolds (known as Reyn) McCullough was raised on Catalina Island in Southern California. When he returned from serving as an Army paratrooper in WWII, he got a job in a men’s store in Avalon, the island’s biggest city. With fashion and marketing skills, he bought out his employer’s shop and changed the name to Reyn’s Men’s Wear. 

Expanding to six stores throughout California, McCullough traveled to Hawaii in 1957 and became one of the first businesses to open when the now-iconic Ala Moana shopping center in Honolulu debuted in 1959. The company began selling top-line men’s resort clothing, which remains its mainstay. The apparel is made with combed cotton and spun polyester.

The company’s name is the combination of McCullough and Ruth Spooner, who in the 1950s began making surf trunks. The duo began working together in 1961. Reyn Spooner is now owned by Aloha Brands. 

reynspooner.com