I work in an office setting and the dress code is pretty lax. I get by fine in khakis, button down and some JM venetian loafers. If I wore a sport coat people would think I had a job interview or something. I would like to find a well made shoe that steps my game up slightly while not spending more than say $300 or so. I read a thread on here and it gave me a few ideas but I am trying to narrow this down. I am pretty clueless about clothes and I am pretty sure I don’t have a “style”. My goal is to look professional and preppy (for lack of a better term). I want to be able to wear my uniform (BB or polo button down, pressed khakis, etc) but also dress it slightly up or down (i.e. jeans on the weekends or with a sport coat if need be). I don’t know enough about brands to be picky other than I want better quality that the usual mall suspects (Johnston Murphy, Cole Haan, etc.). I have had those and they seem to fall apart in about a year or so. My research says I can do one of the following: 1)Beefroll pennys (weejuns, AE kenwoods) 2)Saddle shoes (AE Sheltons) 3)Blucher (Macneil, Walton) I have been wearing venetians but I am open to pennys (no tassle). I have looked at the rancourt venetians and they are nice but due to the short heel on them they don’t look substantial or dressy enough. I am not sure about which way to go in terms of wingtip, plain toe, etc. I want shoes with personality but I don’t want them to draw too much attention either. It is hard to find a balance. For instance the Walton looks like a nice clean shoe that has that one seam to break things up whereas the macneils are really ornate and might be a bit much. As for the saddle shoes, I kind of like them because I don’t see many people wearing them and yet they are kind of low key. I don’t live close enough to a store that sells these shoes so it is hard to just try them on an see how they look/feel. I would appreciate any thoughts to help me figure out how to make this simple choice. We need a flow chart for this stuff.