Which items of vintage clothing would you never wear? And why?

[Shangas]

Funnily enough I feel the same way about morning dress. I so identify it with the Ascot/Four Weddings and a Funeral set that I could never bring myself to wear it. I do have a boater though...

I was reminded at once, of this photograph from...1937, I think it is...

[Two Types]

I was reminded at once, of this photograph from...1937, I think it is...

I love that photograph. Back in the 1980s I was working in the press agency that had the copyright on the picture. I was contacted by a journalist trying to find out more about it. A few weeks later the son of one of the boys contacted me to buy a copy of the photo. I put him in touch with the journalist, resulting in the newspaper reuniting some of the boys.

[Vampyre Master]

I can see as how you might have a certain ambivalence to the bowler. In the context the bowler, so identified with the City Gentleman (or Public School Man), could in a sense, be seen as the adult version of the Public School Boy's straw boater in terms of being a symbol of class.

for me its the Boater, I look like someone just sliced the top of my head off
VM

[Chasseur]

For me its some of the more "preppy/trad" items like boat shoes, tasseled loafers (or any loafers really), madras shorts, red trousers, etc.

They just bring up too many bad memories of preppies in high school, and the loafers remind me too much of some of the more smarmy people I've worked with in government or business. Seems like there is this unwritten rule that if you are a dishonest person in a white colar job you have to wear tasselled loafers. Note: there are great people who do wear them (I am not trying to insult Loungers who like them), but almost all the disagreable people I've worked with do wear them. This has remained true everywhere I've lived in the US, from Washington, DC, to Honolulu and points in-between.

[Pompidou]

I try and keep some semblance of casual at all times, and can't ever see myself wearing bowties, ascots, cummerbunds, or pocket squares. Business casual is as formal as I go.

[Cobden]

Outside of certain settings (that is to say, re-enactment, photoshoots, etc) I also wouldn't wear a bowler; though for slightly different reasons to those above (as it would be rather hypocritical of me). I just think it's gone from a piece of semi-formal headwear to almost "comic national British dress". Wearing a bowler about strikes me as rather akin to a Scotsman actually wandering around in a kilt and woad, a Bavarian in lederhosen, or an Irishman in a green suit with a buckle on his hat - too stereotypical, and almost in the realms of a send up of Englishness.

[Gene]

They just bring up too many bad memories of preppies in high school, and the loafers remind me too much of some of the more smarmy people I've worked with in government or business. Seems like there is this unwritten rule that if you are a dishonest person in a white colar job you have to wear tasselled loafers.

Loafers are kind of my thing, but tassles make me cringe! Pee Wee Herman...

[Flat Foot Floey]

For me its some of the more "preppy/trad" items like boat shoes, tasseled loafers (or any loafers really), madras shorts, red trousers, etc.

Yes. All of them. I don't even had contact to any preppies. I just think they look ugly and maybe reminds me of pretentious fashion bloggers

[herringbonekid]

formal wear holds zero interest for me; white tie, tails, top hat, wing collars etc.

[Two Types]

formal wear holds zero interest for me; white tie, tails, top hat, wing collars etc.

I can understand that. I can foresee no situation where I would need to wear tails. That said, if I ever happen to be invited to a formal event of that nature, I suppose I would make the effort and try to find the right outfit.

Your comment made me think of when a friend and I attended the Summer Ball at university. A third friend refused to attend on the grounds that he would be expected to wear a dinner suit, which he described as "the uniform of reaction" (it was the 1980s).