Mixing hard working utility with casual style, the Red Wing Work Oxford ($275) lets you transition from worksite to dinner date with minimal hassle. Features include an Abilene leather upper, a Goodyear welt, and a thick sole that will keep your heels happy all day long.
Short of sawing through your shoes, it's hard to imagine what all the various components look like. These Feit Hiker X Ray Boots ($315) get around this by using a transparent sole that lets you see the bamboo shank, cork footbed, and thread weave from underneath, while offering plenty of more worthwhile features like Horween Chrome Excel leather uppers, hand made Goodyear welts for added durability and strength, and two tone hiking laces for an added bit of style.
As far as "upscale" Chuck Taylors go, we're big fans of John Varvatos' upgraded All Stars — but if the rock/punk/distressed style isn't your thing, check out these Converse Chuck Taylor Clean-Crafted Oxfords ($100). These strikingly plain Chucks are upgraded with fine leather and trimmed in suede to give the classic sneaker a decidedly more subdued look while still differentiating themselves from the ones you can buy at JCPenney.