by Karen Alberg Grossman

The oldest trade group of its kind in the U.S., The Headwear Association started out as a chance meeting of hat makers and retailers during a spring 1907 trip to Pittsburgh. The first official dinner was held in NYC at the Waldorf Astoria, the purpose simply to “encourage the spirit of friendship and fraternity in the hat trade.” Ironically, today’s mission is not all that different: to promote hat wearing and the headwear industry throughout the world and to foster good will and fellowship among those so engaged.

Always held in early spring and, except for the pandemic years, at the beautiful Central Park Boat House, the event remains a highlight for hat aficionados across the globe. For the past 15 years, the association’s mission has evolved to include disseminating sun protection information, giving out wide-brim sun-protective hats to communities in need, and distributing warm winter hats to the homeless.

And the 2022 headwear award winners are: Retailer of the Year Jack Kellogg of Hatman Jack’s in Wichita, the Ben Rosenthal Award to Bill Stein of Dorfman Milano, the Lieberman Award to Gerry Miller of HatCo, and the FIT Scholarship Award to Alejandro Guillen. The board also annually selects celebrities into the Headwear Hall of Fame; this year’s entries were Taylor Swift, Kate Winslet, Garth Brooks, Billy Porter, Jane Seymour, Chris Paul and Bryson DeChambeau.

As Jack Kellogg of Hatman Jack said at the dinner, “The right hat will make the customer look taller, thinner, more interesting. A hat will make or break your entire look.”

For more info, check out TheHeadwearAssociation.org.


  1. Congratulations to Gerry Miller for winning the the Lieberman Award & to all the other award recipients.

    1. Karen Alberg Grossman,
      Is it possible you look even more interesting AND more beautiful in this photo??

Leave a Reply

Your email address will not be published.