I'm still on the fence about what shoes to get. Prolly get a pair of plain-toe heapo-cheapo oxfords from Ross or something. I'm in a pair of Florsheims that have utterly disintegrated, although they have been hella-comfortable, easy to shine, and airport friendly up until they decided to dissolve. Can't really justify shelling out the $100+ for Rockports or the like when I know they're just going to get scuffed, scratched, gouged, and will look like hell in two months anyway. Then again, there's the comfort factor... Yup. Still on the fence.
Mind you, this is coming from the guy who still runs around the terminal with his 'Little-Ghetto-Johnny-I'm-a-pilot' kit, replete with Office Depo flight case, Ross rollaboard, and Officemax 2" binders for my Jepps. First year at the regional's a little rough on the 'ol pocketbook.
Gotta say though, I just shelled out a Jackson for a Van Heusen tapered pilot shirt and I can't be happier. Eyelets for the wings are niiice. So's the stain-resistant coating, although that makes it a bit hard to starch. The sleeves are cuffed, good fitting, and hold a crease well. The cloth is pretty heavy oxford pinpoint, and the stitching and buttons seem pretty tough, so I think It'll last. Damn sight better than those thin flimsy poofed-out Cintas POS's. Not to say that there's not a better pilot shirt out there, I'm just happy with mine. And no embroidered wings for the love of god! Those are nasty-lookin'.