Settles likes jazzy but elegant clothing, like this plaid Italian designer suit. Though it retailed for a budget-busting $4,200, the bargain shopper paid a small fraction of that price at Filene’s Basement in Newton. Unless you’re in sales, banking, or law, you can pretty much wear whatever fashion footwear you want, says Settles, who sees casual styles on businessmen all the time. He prefers simple and conservative shoes, like these Italian leather oxfords from his favorite store, the Newton Filene’s Basement.