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I’ve said before that dating hats is difficult—you often have to judge based on style and materials more than their labeling. Some are easy, such as my mod-print hat that pretty obviously comes from the mid to late sixties. In addition to the material's distinctive colored print, the material feels like it is from the sixties—a puffy polyester that you couldn’t find today. However, this green and yellow hat was a bit of a puzzler for me. I bought it as part of a lot from an online estate sale, along with the big pink flowers hat and the sweet peas hat. (The lot contained one more hat, which I have yet to wear). I already wrote about how excited I was about the sweet peas hat, but I also was pretty excited about this hat. I love its rich and fairly unusual color combination. From the picture, I judged the hat to be from the 1950s—and perhaps early in the decade. My opinion was based on the shape, which reminded me strongly of the Christian Dior New Look hats with wide, downturned brims that he introduced in the late 1940s. The New Look, with its voluminous skirts and nipped waists, was a reaction to the businesslike austerity of World War II fashion. After the war, with rationing over and women exiting the workforce (often not by choice) the emphasis was on femininity and elegant indulgence. (For another New-Look influenced hat from my collection see this black platter hat.) Here is a picture of a New Look Dior dress and hat from the late 40s. Notice the distinctive shape of the hat and the structured dress with a flowing skirt. So I thought I had a good idea of the hat’s date when I bid online…until I picked up the hats. I then discovered that this hat was not natural straw, as it appeared, but a stiff, plastic-feeling material that glistened a bit in the light. Now I was puzzled. I have a couple of cello straw hats from the 1960s (including one of my grandmother's hats), but that material has a very different look than this material. The only other hat I have in this stiff, tightly woven synthetic material is the gray mini-top hat (a classic shape difficult to date). So this green and yellow hat's shaped looked like it was from the 1950s, but its material made me wonder if it might be from the 1960s instead. The internet to the rescue! In the course of a deep dive into the history of synthetic straw, I discovered that a couple of types of synthetic straws were used during the late 1940s and early 1950s. From online sources (including the Vintage Fashion Guild) I learned that this hat might be either wholly synthetic or natural fibers coated in synthetic material. Milliners liked these synthetic materials’ sheen and shape-holding abilities. Notice how sculpted this hat is, in the back especially, with sides nipped in and the back folded. So the material doesn’t rule this hat out as a 1950s New Look influenced hat, though as usual I can’t date it with 100% certainty.
Sometimes when I wear a new hat to church, no one notices. But this one is so unlike any of my others, people asked me if it was a new hat. I paired it with my cute picnic dress—featuring a feast of deviled eggs, tomatoes, cucumber salad, sliced cheese, tinned sardines, strawberry layer cake, cookies, and champagne. Also featuring butterflies and ants crashing the party. The dress is not vintage, but has something of a 1950s’ shape, perfect for this hat. In fact, while we were in the park taking photos, I noticed my shadow had a great New Look silhouette!
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AuthorAnn Hillesland writes fiction and nonfiction and collects hats. In this blog she vows to wear (not just model, but wear out of the house) every one of her hats, blogging about their histories and their meanings for her. Archives
May 2026
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