So, Rudals asked me about the thought-process behind the outfit I wore together today and my answer touched upon the fact that it was influenced by a somewhat humorous interpretation of the wide-boy look.
I've always had a fondness for the stereotypical clothes associated with this somewhat degenerate & shady yet likeable & amusing stock character. I doubt the term translates beyond British shores; Wikipedia gives the following reasonable definition: "a British term for a man who lives by his wits, wheeling and dealing."
I'm not quite sure why the character appeals, as my respectable background is pretty much the opposite to that of the wide-boy. But I've always been fond of those who aim high, and have nothing but chutzpah and native wit to get there. You might also know the wide-boy as a spiv, a barrow-boy, or a chancer. They're not con-men, gangsters or pimps, those are different. No, the wide-boy is much more on the borderline between petty criminal and legitimate entrepreneur, wanting to be the latter but sometimes having to shade into the former to make ends meet. At the more legitimate end, you have traders (financial and otherwise), estate agents, small business owners, etc, etc.
Leaving aside the sometimes dangerous and unglamorous reality of the life, in fiction, the character is frequently something of a likeable cheeky rogue, who enjoys clothes and has no shame about breaking with the social sartorial norms of the elite in favour of subversive flashes of colour & pattern. You can definitely see something of this in the outfit I wore today, for example. I don't wear that kind of thing as often as I'd like, but I do try to slip in a little of it. Those who know what I wear will see its influence in my tie collection, for example.
This look is pretty much the polar opposite of what SF tends to favour, which is much more of stealth wealth, pseudo-aristocrat/plutocrat look as exemplified by the ongoing Italian CBD thread & Friday Challenge this week. But I wonder if there are any other fans here of this - by alternating turns slick and earthy - kind of vibe?
(the fact that this thread coincides with the Cheltenham festival this week is a happy concidence; the races can be an epicentre of real-life spivtastic characters. I grew up in a town where we got the afternoon off school on the day of the biggest race of the year, and we were just round the corner from the track. That must have influenced me on some level too.)
Famous wide-boys in fiction below; feel free to post more examples!