to the Ascot races in 1935. The Prince of Wales looked characteristically handsome in a smart grey top hat while and his companion, Wallis Simpson, wore a curiously utilitarian small, brimless hat that looked almost as if it was part of a uniform. Until diving into the archives to prepare this series, I didn’t realize these two had made an Ascot appearance.
Photos from Getty as indicated
Royal Hats 
I enjoyed seeing this picture of the famous couple. I believe by this time she was a regular companion of the Prince. While she had her clothes custom designed and was very neat in her appearance I seem to recall from my reading that she was very conservative in her styles. Even her hair was conservatively styled. The hat may have been trendy, but not what we expect for Ascot today!
I googled “hat styles of the 1930’s” and as unattractive as this hat is, I’m not so sure that it’s that out of character for the styles that were prevalent in that era. If you look at this page:
https://vintagedancer.com/1930s/womens-1930s-hat-styles/
you will see a number of hats that don’t look any less like delivery man’s caps than the one Mrs. Simpson is wearing. (Love those prices too — scroll down to see some of the advertising shown on the page!)
As surprising as it is to learn that she accompanied the Prince to Ascot at all, it’s possible that the decision was made on short notice and she didn’t have time to obtain a fancier Ascot-level hat. Just a thought.
Thanks for the fun link, Matthew. That does indeed give us some perspective on hat styles of the 1930s. It still seems strangely uninspired for the fashion-conscious Mrs. Simpson.
Matthew, that link is excellent; it’s great to have some background when we look back at these hats from other eras.
The Duchess of Windsor’s style in the ‘thirties has always struck me as rather low-key (more in the line of traditional “strict” Parisian chic, compared, say, to her contemporary Queen Elizabeth the Queen Mother). But perhaps an understated look was not inappropriate while she was keeping a low public profile.
Mcncln, I think you hit the nail on the head. I believe Mrs. Simpson was known for her strict Parisien style chic: sober, very elegant and, as she became the Duchess of Windsor, very expensive! A good example of her understated style was her weddingdress from Mainbocher.
Wonderful article Matthew! I love those thirties’ hats. I’m always amazed by the variety of styles from the second half of this era. Thank you for sharing!
Looks like she forgot her real hat and hastily did some origami with a carrier bag!
I wonder if King George V had kittens when the Prince of Wales showed up to Ascot with his girlfriend, Wallis Simpson? About her hat…I agree with HatQueen that it looks like a cap that a delivery man would wear. Surely David could have sprung for something gorgeous unless this was couture and I don’t know it? Or it could be that she didn’t want to stand out? Curious and curiouser.