Yeah yeah, Red Wings are all very well. And sure, they last a long time and look nice. But if you're looking for a work boot with real panache and heritage, the dealer boot cannot be beaten.
Seen on the feet of Romany horse-whippers, Northolt ex-borstal boys and every rockin' n'er-do-well in 1980s London, dealers have to be tan with a brogue top and AirWare sole. No arguments. (Leather soles are sometimes acceptable but beware, you may be mistaken for a toff with an actual horse.)
In the '80s, even Holts didn't have 'em. You had to go to Southall Market or the manufacturers in Northampton.
And if you're worried they don't have enough SoCal-cool-cat-class, check the early scene in Hells Angels on Wheels where Jack tips a rival MC member headfirst down the bog during the bar fight. What's the guy wearing? Dealers, bro!