Thanks for all the advice! I'm in agreement that I shouldn't dive head first but build my wardrobe slowly. Few follow ups for anybody still following:
Regarding pants, I have a big seat and thighs so pants have always been the hardest thing for me to find. A few weeks ago I went to Brooks Brothers and could not find anything that fit properly. One of their more casual pants fit in the thigh area but was too loose everywhere else. Any other brands I should try?
How about socks? I wear size 12 and always seem to stretch out socks cause they are too small.
At a place like century 21, should I look for a particular brand?
Will def check out Allen Edmonds. I see it gets a lot of love here.