I was actually thinking of suggesting items 2 and 4 -> I've bought one "imperfect" from allenedmonds before without problems. I think #1 (AE burgundy punched cap) is a little too much for used, #3 (AE burg wingtip) is ok, #5 is a little trendy for me and I think would be tricky for coordinating with your suits but fine for going out, #6 (mezlan) would be a better choice over #5, either of the shoes on #7 from bennies would be great, and #8 and #9 are decent choices as well. I'll definitely get one of the grensons on page #7 before I get #9 - especially since you said you were a narrow (either a or b) and I would guess that the tyrwhitt shoes are medium widths. Is there any way you can try some shoes on before you buy and report back - like perhaps hitting a Nordstroms during the after christmas sale and trying on shoes on the sale racks - or even the shoes on the racks at the outlet malls? I feel guilty too actually bother a salesman for trying on something I'm then gonna buy online, but not from the sales rack, because sometimes I buy then. If you were armed with a bunch of sizes and brands, we could probably eliminate a few sizes. If it were me, and I was starting out, I would go with the grenson's on #7. But they will basically take all of your budget. Perhaps one of the grensons, and another shoe at $50-70?