Since I am sort of an Allen-Edmonds buff, I thought I toss in my 2-cents worth. A-E only has a couple of dark brown dress lace-ups--the Byron and the Seneca. The Byron is A-E's second most dressy lace-up after the Park Avenue. I would only wear it with a sport coat and tie at the most casual, preferably with a suit. The Seneca is, I think, at its best on men with short, broad feet--it has a very elongating effect that made it look sort of clownish on my size 13D feet. In the lighter brown Antibes calf there are more options--the Park Avenue (very dressy), the Cortland (kind of boring), the Hillcrest (nice if you like the bicycle toe, which I do not), the Hancock and the Harrison. The latter three would probably be the most versatile--conservative enough for most business situations, yet they would not be out of place with more casual attire. I have the Hancock, may pick up the Harrison and/or the Cortland one of these days.