I’ve always wanted to get out of an impressively oily and macho aircraft, divest myself of the flying suit, James Bond style, revealing a tux underneath, then go and prop up the bar...
To get back to the OPs question:
With winter upon on us I was considering buying a leather flying jacket.
However would I look like a bit of a knob walking around my local club wearing a military type flying jacket???
If the club in question was an officer’s mess, then you would blend right in. Otherwise, as others have pointed out, the type of aircraft makes a big difference: C150, high on the “knob” scale. Biplane, aerobatic, vintage, military, open cockpit, etc. no problem. Wings, stripes, badges and the like looked good on Chuck Yeager (and Tom Cruise) but for your average UK GA pilot learning to fly a Tomahawk, not so much.
Mind you, I do a lot of gliding and some people wear... Aaargh! I don’t even want to talk about it, it’s so horrible!