I hear you, Reb Steve - on a more practical level, I wonder what would happen if I knock on the door for a shidduch, and when the father/brother/bro-in-law opens the door, we both do a double take because we know each other from a GYE meeting or something. Could definitely be awkward!
As an aside - The size of the breakfront is one thing, but types of shoes? They don't say anything inherently, but if a guy goes to a yeshiva where the standard dress code is to wear plain black shoes, and this guy (for an extreme example) always wears white sneakers with neon colors thrown in, you might want to find out what's up with that. Not because of his frumkeit, but because of his obvious need to stand out and be different.