When did the American male start thinking that dressy meant those God awful slip ons that a few have posted above? Is it because kids starting wearing velcro straps on their shoes so no one knows how to tie laces?
It's a very strange phenomenon. The mid-20's is such a hilariously awkward age to observe among males. We know that the early teen years are classically awkward in that voice-changing, hormones-raging, identity-searching way that is somewhat endearing (to a point).
But the early/mid(/even late 20's for many) is a period where the American male is presumably trying to begin some sort of professional career and has perhaps recently graduated from college/grad/professional school. Suddenly the once or twice yearly need to put on anything that resembles "dressy" becomes a routine thing, but most guys apparently aren't ready for this and panic. And then, almost inexplicably, they almost intuitively start collecting only the most hideous articles of clothing and footwear under the assumption that, since all the other awkward 24 year olds wear black square-toed slip-on hybrid sneaker/dress shoes, this is an honor befitting of him as well.
Thus the barrage of baggy "relaxed fit" Dockers, clunky rubber-soled Skechers, and awful dark-colored (red/dark navy blue/black/gray) baggy button-up shirts that ensues.
The unfortunate ending to this tale is that, for many men, they never actually grow out of this awkward phase.
And it really doesn't require anything remotely close to a Herculean effort to dress reasonably well. By understanding a few
very basic guidelines and having an appreciation for how clothing is actually supposed to fit you, you can go from "slob in your father's oversized hand-me-downs" to "debonair" in a few easy steps. I know some dudes are worried it's not "cool" or "manly" to give a damn how they dress. For people with that kind of mindset, they're probably beyond help as it is.
Anyway, I greatly digress. If you want to wear disgustingly ugly shoes because they are super comfortable, that's ok as long as you don't operate under the false assumption that their look is anything but terrible. Believe it or not, there are quite a few "nice looking" shoes/brands of shoes out there that are very comfortable. At the risk of channeling the user neusu here [for those of you on the "I hate surgery residents" thread], to the same degree that it's not accepted to wear sneakers with slacks in a work setting, there is some element of "suck-it-upitude" that has to come into play here.