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Vintage Hat: Raymond Hudd

Raymond Hudd came from Michigan to study art at the School of the Art Institute of Chicago. After briefly trimming windows in Chicago stores, he opened his first shop in 1950. His creations adorned the heads of many famous and not famous women. He was proud that his friend, performer Phyllis Diller had 500 of them. His moment in the limelight was the Chicago History Museum exhibition, Hats Over the Edge, in 2001. The featured photo was Raymond's favorite hat.

Vintage Raymond Hudd...can't go wrong with pink and roses.

Sack of Potatoes Turban by Raymond Hudd |

(♥) Phyllis Diller as a Keystone Cop, New York City, September 1963. From A.P. Images. “I gotta rash that’s movin’ so fast I can hear it.” RIP Phyllis Diller, an iconic comic who turned self-deprecation into a fine art.

Raymond Hudd hat daisy

Raymond Hudd hat bees

Raymond Hudd hat with lilacs

Raymond Hudd hat of roses on cake

Raymond Hudd pillbox hat with cabbage

Raymond Hudd hat of cauliflower

Raymond Hudd hat of strawberries

Raymond Hudd pillbox hat with rolls; Let Them Eat Cake series

Raymond Hudd pillbox hat with frogs

Raymond Hudd pillbox hat with mice

Raymond Hudd pillbox hat with donkey

Raymond Hudd pillbox with elephants

Vintage Blue Sequin with Feather Cocktail Hat by FrouFrou4YouYou, $75.00

Kentucky Derby Vintage Straw Hat with Wide Brim by FrouFrou4YouYou, $100.00

Vintage Dark Green Felt Brim Hat with Black by FrouFrou4YouYou, $40.00

Felt Raymond Hudd hat: Personal collection of Mary Robak from Linda Feigenheimer Estate

1967 Raymond Hudd winning hat for Drake Hotel in Chicago Easter contest. He named it "Hat." He made a matching tie he wore to the event.

  • arturo schultz

    thanks for sharing. I was with Raymond when he made this hat. He was my friend for over 50 years /)

  • Mary Robak

    Arturo, so good of you to add this comment. Perhaps you would be so kind as to share some stories about Raymond, as I adored him, tho only knew him a short while.

  • arturo schultz

    I first met Ray in 1962 when a good friend brought me to Chicago. We all became lifelong friends and at times lived together. We shared a warehouse loft for a few years at 411 N LaSalle. We had the entire floor for $200 a month including utilities and thought :) we were being ' overcharged" I'd gladly pay that now ! I will tell you a story from there. Ray was all dressed in a Tuxedo to go to Judge a Hat show at the Palmer house. We needed a key for the elevator and the door to the street and Ray misplaced his keys, so he called a cab. He told =them to pull up on the side of the building and when it arrived paraded all dressed up down the escape to the secon floor and stepped on to the ladder that than unfolded to the street and stepped off right in front of the cab carrying three or four hat boxes with hats that were prizes. :)

  • Mary Robak

    That was priceless. You have more than made my day, and it is only 6am! I can't say I have any news clippings from any events at the Palmer House, but he certainly did well when winning himself at The Drake. One of those winning hats had just been in a lot auctioned off by the estate of Phyllis Diller, one with a lot of black edged white ruffles. Will look forward to hearing more from you. Email would be easier, if you like. Maryrobak@comcast.net.

  • arturo schultz

    will do.... on Way to Ny and Connecticut :)

Green felt hat with feathers by Raymond Hudd Chicago