I have a friend who, back in 1978, was having his suits and boots made to measure.  He still has the boots, tucked away in his garden shed.  When I reminded him of this (and he always dressed with style, even after marrying and raising children) he said, 'I was a dandy, wasn't I?'
Wry observation from Eddie Condon (who knew Bix Beiderbecke, said to be a shabby dresser): a dandy is too clothes-conscious, thus trying too hard.  A gentleman, on the other hand, always dresses well 'because he knows no better'.