Originally Posted by emptym
For warm weather, probably a burgundy loafer. For cool/cold weather, probably a dk brown chukka. But for any weather, I suggest a pair of black slip-ons
Hm, I was skeptical about the black slip ons suggestion, but the photo of you in that thread indeed looks pretty good.
I have a pair of black EG Picadilly loafers that I'm not sure if I should keep. I've been thinking about selling them on eBay, but expect to lose money on the sale given how much I paid. Do you find yourself wearing black slip ons often? Are penny loafers not included in this rule?
As for the OP, I strongly believe dark brown plain toe derbys are the most versatile shoe you can buy. Presuming you don't wear business suits most of the time, that is, or shorts and t-shirts. For anything in between, brown derbys are usually a good bet, and for almost any season as well (depending on where you live, of course). They're nondescript, but that's to their advantage in this situation.