6. Jackie Kennedy and Halston

Jackie Kennedy in a signature pillbox hat by Halston. Image via Wikimedia Commons.

While perhaps more of a working relationship than a gossip-over-cocktails kind of friendship, the tie between internationally acclaimed designer (and notorious party-throwing bachelor) Halston and first lady Jackie Kennedy Onassis was vital to each another’s success and legacy. At the young age of 26 (and before he dropped the majority of his hame), Roy Halston Frowick made his way from Chicago to New York City with millinery skills as the only background for his fashion business. Luckily, his ability to make a hat would soon serve both him and Jackie pretty well. It was Halston who would design the First Lady’s signature pillbox hat, and the fact that it was on the head of the First Lady would make Halston’s hats signature. 

At this time, the Kennedys were on the campaign trail, while Halston had left his frolicking mentor and friend, the eccentric designer Charles James, at the Chelsea Hotel to go work for Bergdorf Goodman. Meanwhile, the future First Lady needed hats for the road. It was her almost vehement distaste for hats altogether due to her large head that solidified her and Halston’s relationship– they had the same size head.

It wasn’t long before the pillbox hat would become Jackie’s hat of choice. “I remember the day Halston brought the pillbox to Mrs. Kennedy at the Carlyle,” said President of Bergdorf Andrew Goodman. “You’re so young to be so successful,’” she replied to him. Kennedy reportedly even cried when she had to tell Halston that her husband had made a promise to a different designer for the honor of creating her inauguration look. 

Thus, Jackie Kennedy became a fashion icon and Halston put his name irrevocably on the fashion map. Halston’s salon subsequently took off and soon was the go-to spot for New York City’s elite. Everyone from the likes of Lauren Bacall and Bianca Jagger to Barbara Walters would come to his salon for lavish lunches and make their way to the now-New York City landmark Halston House for swanky soirees. 

On a side note, quite the opposite of a friend actually, would become a stalker of Jackie’s. This was the infamous paparazzo Ron Gallela, who used to troll around her Fifth Avenue apartment before she filed a restraining order.