I don't wear suits often so my list is based around more casual wear. Black Cap-less Oxfords - good for black tie as well as normal wear. (don't actually own these yet, meaning to for a while to replace a couple of crappy pairs) Brown brogues - I have some Paul Smiths that dress up or down pretty well Rubber soled but presentable country boots - I have a pair from herring that whilst not smart are passable in smart casual situations but have handled wet weather and a bit of snow just fine. White Converse low-tops either a Chelsea or Chukka boot in brown leather or suede.
1. MTO Corthay black boots in 001 last
2. Berluti demesure (sp?) brown wholecuts. There was one in b&s in my size a few months ago. I couldn't afford it at that time :/
3. Double monks in cognac. Either a Vass U last or C&J 348 last
4. EG brown jodphur boots (sp?) in 888 last
5. A pair of G&G in a sleek last. Don't know much about G&G but I definitely want one
I wish I have the money for all of them right now.
Longwing Blucher - Alden, AE, Vintage Florsheim Imperials all acceptable. Cordovan is the most versatile for wearing both casually and for business, but brown or black can work. Penny loafer - back in the day it was Bass Weejuns, but the quality is just not there any more. Stick to Alden or AE. Again, the cordovan Aldens are probably the most versatile. Boat Shoe or other casual slip on - Quoddy trail boat shoe, canoe moc, or blucher moc all good. Personal choice as to sole color (white, brick red or brown). You can save a little money up front by going with Sperry or LL Bean, but they will not last nearly as long. Chukka or Desert Boot - Suede of course. Clarks are fine, but Aldens are really nice. Classic Sneaker - Chuck Taylors, Jack Purcells, Stan Smiths, Rod Lavers, PF Flyer Bob Cousys. It's a personal choice for style and color. You will also need a sturdy pair of boots if you live in a winter climate, but that is another thread.
Black oxford captoe - JL Stafford on the 7000 last
Brown blucher punch toe - JL Brackley, Museum chestnut
Dark brown suede captoe - Loake Durham
Kangaroo chelsea boots - RM Williams
Sturdy soled trail shoes - Saloman