Jack Peffley: A tall tale

Jack Peffley is known for wearing the pants on St. Armands Circle — whether the pattern is polka dot, psychedelic green or 70s-era flowers.

But one thing that hasn’t changed in his 35 years in the area or the more than 20 years in which he’s sported the pants: Despite his 6-foot-8 status, Peffley has never grown too big for his britches.

On May 30, the face of St. Armands, who was most recently general manager of Marcello Sport, said “goodbye” to the Circle and “hello” to retirement in Myrtle Beach, S.C.

"Jack is an institution in himself," St. Armands Executive Director Diana Corrigan said. "He has given tremendously to the board, the association and to the St. Armands community. He has not only been a partner that I've worked with, he's been like my brother. It'll be hard not having him here. We'll all miss him."

When Peffley opened Philip's Menswear on Longboat Key in October 1980 at what is now the Shoppes of Bay Isles, the island's population was only 4,843, compared to 7,082 today.

"I looked at the area, studied all the golfers and what they wore and thought it would be a good place to open a store," Peffley said. "They were still building the golf course, and there were no homes yet back in Bay Isles."

Peffley and his wife, Nancy, opened a second Philip’s Menswear location on St. Armands Circle in 1983, and Peffley immediately became involved with the St. Armands Circle Association.

"Behind the Columbia (Restaurant), there used to be a water tower and an old derelict parking garage," Peffley said. "One of the very first things I got involved with was getting that parking garage and water tower torn down and expanding the parking lot that’s there now."

Peffley also brought an offshore grand prix to the Circle, a two-day event where powerboats were put on display. It became one of the Circle's largest events.

"We held a record for the number of kegs sold for one day in the city for the event," Peffley said.

The event eventually became too big for St. Armands and was moved to the Van Wezel parking lot in the early 1990s.

"Jack started the whole concept of bringing events to St. Armands Circle," Andrew Vac, Peffley’s friend and fellow Circle Association member, said. "It drew crowds of people here like Sarasota had never seen before."

In 1993, Peffley's company bought Taffy’s Menswear on the Circle, and the Philip’s Menswear store on St. Armands became Taffy’s.

Peffley adopted his signature pant style after buying Taffy's and attending a trade show (see sidebar). He displayed the pants in the store window, and they began selling immediately, and the store became Loudmouth's single biggest-selling retail store in the country.

"I figured that I would bring them to the greater Sarasota area by starting to wear them," Peffley said. "Being 6-foot-8, I was spotted everywhere. Everybody knew me by my crazy pants and shorts. I would go to meetings, and men would be in blazers and suits, and I would be wearing Loudmouth."

In addition to the grand prix and parking lot implementation, Peffley was instrumental in setting up for various events on St. Armands, especially the holiday decorations.

 "If you can't stand tall and look straight ahead and be proud of who you are and what you do, then you need to make changes in your life," Jack Peffley said

"You name the events, and he was always there to support and help it," Bill Carman, Circle Association vice president and director of communications, said. "He was one of the key figures on the Circle. He was always there helping to get things set up. He was a right-hand man, and without him, so many things wouldn't have gotten done."

In 2001, Peffley was chairman of the Circle's 75th anniversary celebration.

"We all had a lot of fun with the 75th," Carman said. "He was dressed up in a purple suit and looked like a gangster. All of the items sold on the Circle had to be the same price as it was in 1927. Jack did a great job."

Philip's Menswear closed in 2009, and Taffy's closed in 2012. After Taffy’s closed, Peffley took on his role at Marcello Sport, which remains open.

For Peffley and his wife, retirement is a new challenge.

"It’s been a big adjustment for me to leave the Circle, my friends and my house, but sometimes change is good," Peffley said.

But he knows fully retiring from his role in Sarasota would be difficult because of the many roles he played.

Although Peffley enjoys retirement so far, he treasures his time on St. Armands.

 "If you can't stand tall and look straight ahead and be proud of who you are and what you do, then you need to make changes in your life," Peffley said. "I'm proud of what I did for the community and for St. Armands. Thousands of people enjoyed what I did. I feel good about that accomplishment."

 Despite his retirement from working, Peffley doesn’t plan to retire his signature style.

“I wore my pants on the pier one day, and everybody was looking at me,” he said. “They’ll have to get used to it here."