I wrestled with the same thing Lsash. Ended up doing the "I'll just get everything over time so I know for sure" approach… so I have White's, Trickers and Alden boots but only wear the trickers and aldens into the office, the whites are just too hardcore for the office.
i saw a pic on baker's Facebook page of kyle's wedding - it was he and all his groomsmen in matching white's semi-dress boots with their tuxes!
I wear boots to work every day unless it's a trip to Indianapolis corp. HQ. We have a business casual attire policy which includes denim, and I take full advantage. But even if I have to wear dress pants I have some nice Billy Reid wing-tip ankle boots that work quite well.
Thanks for sharing your experiences. Many of us love custom made things.
I would like to share this with you guys.