Yes I would love to look as best as I can at any age so I think Cole Haan's are a good option to start out at. As some call them "lawyer shoes", if I upgraded to real hardcore lawyer/CEO what does that say about what is important to me at this age?
Any reason why Doc Martens, LL Bean, Redwing aren't options? Dress shoes are a recipe for dork-dom unless you pull the rest of it together too (at least on the campuses I've been to).
If you have to say it...
Usually mutually exclusive, but in this case, mutually amplifying.