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As for "when am I ready?" You'll never be ready. It works in reverse, you become ready by doing it. - pmbomb
When I was a teen it was all about Michael Caine in the Italian Job, and this suit...
Although his right sleeve is either slightly too short, the cuff on his shirt is slightly too big, or it was cut to wear with a watch, and he's not got one on.
Anyway... Beautiful!
I can't help about the shape I'm in, I can't sing I ain't pretty and my legs are thin
But don't ask me what I think of you, I might not give the answer that you want me to
That said - and despite my love of Duran Duran and early-80s Roxy Music, I look stupid in a suit, so it wouldn't 'suit' me...
"Take these three items, some WD-40, a vise grip, and a roll of duct tape. Any man worth his salt can fix almost any problem with this stuff alone." - Walt Kowalski
"Only two things are infinite - the universe, and human stupidity. And I'm not sure about the universe." - Albert Einstein
Also (pedant alert) Connery is wearing a jacket & slacks
https://www.grailed.com/drycleanonly/cary-grant-north-by-northwest-style
Although you might squeeze Steve McQueen in here anyway
Lets get back on topic fellas!!
Musicians...
If I had to pick someone probably Steve Craddock from OCS days.
I can't help about the shape I'm in, I can't sing I ain't pretty and my legs are thin
But don't ask me what I think of you, I might not give the answer that you want me to
Ronnie fucking Pickering!
I fell in love with her eyes on Army Dreamers, and then started to notice lots of other things about her as my teens rolled on. To me she had it all, even with the sound turned down.
Blokes
I suppose Sid Vicious was the first one who woke me up to scruffy being cool. We were as poor as church mice so that look was achievable. A little before my teens though. Dammers was pretty cool on keyboards playing 'Gangsters'. Prince as I got older, he could pull the chicks, sing, act, play the guitar, pretty darn cool really.
When in England (presumably filming), he used to go riding with my dad!
Not so much a style I (or basically anybody) could pull off however my absolute hero, and therefore my favourite coolest person in general ever would be....
https://www.justgiving.com/page/pianomatt-1000lights