Cross Dressing In Top Hat And Pipe -1930s Photobooth Snap

I didn’t have a post scheduled for today but when this gem arrived in the mail yesterday I couldn’t wait
to share it.

When I first saw the picture, in a poor scan on Ebay, I assumed the subject was a man. On closer inspection, I have considered the possibility that this is a woman in drag.

The somewhat theatrical mien of the sitter, the subject’s effeminacy, soft features and no signs of facial growth are a start towards this assumption. Additionally the combination of top hat, pipe, glasses and a business suit seem to me to be caricature features of a male of this period, which I estimate to be the 1930s, rather than an ensemble worn at the time.

If it were a man dressed for a night out on the town wouldn’t he be in formal wear? I never saw Fred Astaire or anyone else for that matter, in a top hat without white tie and tails. There is also something about the top hat that suggests to me that it is nothing more than a costumers prop. The brim seems too narrow and thin and the silky sheen of most top hats is missing.

It could of course be a very young man dressed for a play or a fancy dress party.

Anyone else have an opinion? Please let me know by leaving a comment.


Approximate original size relative to the larger scan.


  1. Mike said:

    I think your analysis is quite good, but looking at it gives me few clues. I do think he would be a handsome man, but she would be perhaps a bit unlucky in that regard.


      • Mike said:

        At best it is a woman with VERY short hair. I’m sure she is loving, worthy, kind, and creative. Had I been a relative of hers, I would have loved her fiercely.


  2. Whatever the story behind it, this is a truly remarkable, surprising photograph. How lovely of you to share…


  3. Kristine said:

    I agree with the costumers prop. He looks too young, even for that day and age, to have a pipe in his mouth when having a photo taken. It’s an awesome photo, one I would like on my wall. Quite classy.


  4. It’s tough to tell. Wish you could see the eyebrows, it might give a better clue. But, then again, that would remove the mystery and fun of this photo!


  5. Elementary my dear Watson. But I think I’m going for male given the jawline, width of nose and absence of boobs. And the waistcoat fastens left over right…the men’s way. But we’ll never know. It’s a wonderful image though.


    • I think the angle makes the jaw and nose look broader than they really are. I am tempted to see if I can find a photo of a woman in similar pose to superimpose over the top of this one. Might make a good comparison. I don’t see the booblessness as an issue. They could be hidden by the clothes if she was flat chested or strapped down.


  6. Lisa said:

    I think this may be a man – I’m looking at the hair, and I don’t see any hair peeking out from the back of the neck (if it were even a short haircut, for a woman, it would be longer than this hair). It’s a lovely find!


    • You could be right, Lisa. I keep thinking I have seen this face somewhere before in my collection of booth photos – on a woman – but that is just wishful thinking as this one didn’t come with any others of women.


  7. I don’t think there’s any way to tell for sure, but I’ll go for handsome boy playing with ‘fake’ top hat for a picture.

    Liked by 1 person

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