He dresses like he's in a dad rock band because he IS in a dad rock band. Well, a rock band at least. Music has always been a huge part of his life and if that is the way he wants to look and dress then that's fine. It's not my taste at all and I think he looks a bit of a dick but I also admire him greatly for having the confidence to be true to himself.There's probably a mixture of suits vs tracksuit managers. Then there's managers like Schuey and Lowe, who go for the smart casual look.
Then there's Ainsworth, who dresses like he's in a dad rock band. It certainly adds to his character, but there's got to be a reason why a manager who has done such a good job at a small club is still with that club after 10 years. Especially considering the turnover of managers in the EFL.
Anyone displaying even a modicum of ability is generally poached pretty sharpish - Ryan Lowe has already moved on twice in his short managerial career, Rob Edwards left Forest Green for Watford after a single season, Ian Evatt was poached by Bolton after two seasons at Barrow. There are loads of similar examples.
Yet Ainsworth is still at Wycombe after a decade. Maybe it's his style of football but I doubt it. Football is a results business and he gets them.
Similarly, whilst some people cite that he lacks ambition for sticking around at Wycombe for so long as if that is some kind of character flaw I think it's a character strength. It's clear that he has his life sorted, knows what he wants from it and doesn't really care about what anyone else thinks. Again, I admire him for this as it is not something you see that often.