Tommy Bahama marks 30th anniversary, with idea that began on Bonita Beach

What if we just stayed on vacation forever?

It's something that many of us fantasize about, but this meditation on life was inspired during a Bonita Springs snowbird season decades ago, leading to the birth of Tommy Bahama.

Although Tommy's not an actual human, the behemoth Floridian lifestyle brand encompassing products ranging from fashion and home furnishings to food and tropical cocktails is celebrating its 30th anniversary in 2023.

The founders' first foray was menswear, hitting department stores in 1993.

Two years later, what was initially planned as the company's first standalone retail store changed when a real estate opportunity in Olde Naples proved irresistible.

The brand's CEO, Doug Wood, credits Barbara Walker of Neapolitan Enterprises for igniting an idea in 1995 when two of Tommy's co-founders, Tony Margolis and Bob Emfield, wanted to open their first retail store.

It was Margolis, Emfield and their wives who were inspired on Bonita Beach years ago to create the brand.

Tommy Bahama Restaurant, Bar and Store in Naples.
Tommy Bahama Restaurant, Bar and Store in Naples.

The gents thought 1,000 square feet, but Walker showed them a space eight times that size.

The result? Two shops, one for menswear, a second for womenswear, both sandwiching what would become the brand's first-ever restaurant.

From Naples to a National Presence

From opening day in 1996, when it was named Tommy Bahama Tropical Café, locally famous late restaurateur Jerry Alajajian served as the restaurant's general manager for 15 years.

Among Alajajian's early hires: Leopoldo Morales, who encouraged his brother Gus to join him at work.

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With 20 years under his belt, Gus Moreno is the restaurant's longest-serving employee in Naples at Tommy Bahama Restaurant & Bar.
With 20 years under his belt, Gus Moreno is the restaurant's longest-serving employee in Naples at Tommy Bahama Restaurant & Bar.

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Almost 20 years later, Gus is now Tommy Bahama Restaurant & Bar's longest-serving employee who started as a busser yet wears many hats, mostly as a kitchen line expediter.

Morales called the restaurant his "second home. My workmates are family."

He takes pride in being recognized by longtime guests by name and considers them family too. "I've watched kids who dined with their families years ago return as moms and dads introducing me to their kids."

A Naples Daily News dining review of Tommy Bahama in Naples from 1996.
A Naples Daily News dining review of Tommy Bahama in Naples from 1996.

That family-friendly sentiment is echoed by CEO Wood and his boss, Tom Chubb, Chairman, CEO & President of Oxford Industries, Inc., Tommy Bahama's parent company that also owns fashion-lifestyle brands Lilly Pulitzer and Southern Tide.

Before Oxford acquired Tommy Bahama in 2003, Chubb said the founders spoke in "very glowing terms" about the brand's presence in Naples.

He decided to check it out himself.

"That Naples visit crystallized what the Tommy Bahama brand is all about. Seeing the product, the store, and the restaurant against the backdrop of Naples with people enjoying themselves with friends, children and grandchildren, really sealed the deal."

Piña colada cake is an original dessert at Tommy Bahama Restaurant & Bar. It continues to rank as a best-seller.
Piña colada cake is an original dessert at Tommy Bahama Restaurant & Bar. It continues to rank as a best-seller.

"Vacation Mindset" Menus

Chubb's favorite items on the menu include Parmesan-crusted Sanibel chicken and piña colada cake, two of 10 classic items on the menu since day one that still rank as guest favorites.

Among Morales's top picks, he's torn between beef tenderloin salad and the famous coconut shrimp.

And despite Naples being closed for five weeks after Hurricane Ian's decimation for a total gut renovation (all employees were paid during the closure), this appetizer garnered nearly 22,000 orders in 2022.

Coconut shrimp is Tommy Bahama Restaurant & Bar's best-selling appetizer since its opening in Naples.
Coconut shrimp is Tommy Bahama Restaurant & Bar's best-selling appetizer since its opening in Naples.

Todd Vento is the U.S. East Coast regional chef who's worked 20 years at Tommy Bahama, including five years as executive chef in Naples.

He's watched the menu evolve, following food trends with increasing vegetarian and vegan requests. Salad selections are also expanding, nowadays swapping creamy dressings for vinaigrettes.

Mango chicken salad, a hit since day one, will stay on the menu forever.

Grilled chicken and mango salad at Tommy Bahama Restaurant & Bar is a top 5 menu mainstay since opening decades ago.
Grilled chicken and mango salad at Tommy Bahama Restaurant & Bar is a top 5 menu mainstay since opening decades ago.

"Boca Chicken Chicken," which a handful of guests still request, went bye-bye, as did the dessert "Barbados Brownie," earning the chefs "a lot of flack" from Naples guests.

All executive chefs are tasked with finding the best local fresh seafood and produce purveyors. While macadamia nut-crusted fish is on most menus, the fish itself varies. When visiting the Naples restaurant, it was snapper. A quick peek at Newport Beach's menu reveals halibut.

Tommy Bahama Restaurant & Bar's top-selling macadamia nut-crusted fish offerings differ at every location depending on local availability. On May 16, snapper was the fresh catch.
Tommy Bahama Restaurant & Bar's top-selling macadamia nut-crusted fish offerings differ at every location depending on local availability. On May 16, snapper was the fresh catch.

Playing into the fashion line's tropical colors, vibrant vegetables are also a focus.

"When you think of Tommy Bahama, you think of color and fun. We design our food and cocktails for a 'vacation mindset,'" said Don Donley, senior director of culinary and Marlin Bars.

SWFL corporate chef Todd Vento, expo lead Gus Morales, culinary director Don Donley and Naples executive chef Abraham Susser at Tommy Bahama Restaurant & Bar in Naples.
SWFL corporate chef Todd Vento, expo lead Gus Morales, culinary director Don Donley and Naples executive chef Abraham Susser at Tommy Bahama Restaurant & Bar in Naples.

Fashion Meets Food

Though Tommy Bahama isn't the first or only lifestyle brand with restaurants (hello Ralph Lauren and Restoration Hardware), with 21 company-owned and operated locations, it boasts the most extensive presence in America, generating more than $100 million in 2022.

The culinary collection consists of 13 casual fine-dining restaurants, primarily in high-end resort destinations as far west as Hawaii. Others in Florida are in Jupiter, Sarasota and Sandestin.

Marlin Bars are also adjacent to retail stores. This JLB-approved concept debuted in 2017 at Estero's Coconut Point Mall, a patio featuring small plates and cocktails with counter-service. You'll also find them in Florida in Fort Lauderdale (two locations) and Jacksonville, Winter Park and Palm Beach Gardens will open later this year; Lakewood Ranch is in the planning stages.

By sales and guest count, Naples retains its ranking as the brand's No. 1 restaurant, busy no matter the time of year.

Diana Biederman is NDN's food & restaurant reporter. Her husband is a walking billboard for Tommy Bahama. Connect via dbiederman@gannett.com.

This article originally appeared on Naples Daily News: Tommy Bahama marks 30 years; first restaurant, store in Naples