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1930s hat display from famed old NYC Milliner

Posted at 7:04 PM, Jun 21, 2022
and last updated 2022-06-22 00:03:51-04

NAPLES, Fla. — Although money may not buy happiness it sure does get you some nice hats which is kind of the same thing!

Roselyn Stillwagon unlocked the vault of vintage hats created by her aunt, Josephine Tripoli, a famed old-world Milliner at the Carlisle in Naples on Friday.

Tripoli was a well-known Milliner from New York City in the 1930s. Her work was recognized and worn by extravagant designers such as Vera Wang, at her wedding, and other known historical figures like the First Lady Barbara Bush.

Tripoli’s niece, Roselyn Stillwagon said that when Barbara Bush came into the shop, she said she did not like hats. Tripoli found her a headband hat with some fluff on the top, “And Barbara said ‘wonderful’ and bought two more.” said Stillwagon

Aside from Tripoli’s hats being showcased in the Harper’s Bazaar, Vogue, and Vanity Fair, she created the first female pilot's hats for commercial airline use.

“She was like my second mom, we were very close,” Stillwagon said that her aunt would make three of the same hats at once and the best would go to her client, the second would stay in her store, and the third would go to Stillwagon.

“It takes patience,” Stillwagon said that having Tripoli as her aunt helped her learn patience especially when it came to creating masterpieces.

Many Naples residents attended the hat showcase and said they not only enjoyed looking at the hats but also hearing the stories behind each hat.