Top -- T Shirt (cotton), long-sleeve shirt (collared), hoody (zip-up), wind-breaker, water-proofed outer shell, baseball hat, hockey sweater, bomber jacket, workout shirt (polyester performance), workout pullover hoody, undershirt (tank top), long-sleeve undershirt, peacoat (?)
Bottom -- Jeans (selvage for casual/dressy options), chinos/khaki trousers, socks (white and black/navy), corduroys, track pants, athletic shorts, underwear (boxers, boxer-briefs, tighty whiteys), long johns
Formal:
Top -- Blazer, collared shirt (long or short sleeve), under shirt, tux (?), overcoat, fedora/trillby, cardigan/sweater
Bottom -- slacks, black/navy socks, underwear
Addressing issues I've personally faced: SF has ever fluctuating weather -- particularly in commute between the western Richmond District to the eastern Financial District. This means lighter, rain-proof gear that can be easily (and space-savingly) either collapsed into a bag or fashionable enough for the Downtown crowd. Long-sleeve shirts are ideal, as the sleeves can be rolled up or down. Jeans are pretty adaptable, provided there is minimal distressing and embroidery. Riding the bus also is an issue: seats are often uncomfortable, so small pading in the rear of trousers would be nice. They should also have a no-stick or anti-staining finish as bus rides are often filled with numerous, unimagined fluids sloshing about unexpectedly.
Pockets! My pockets are broken down to include space for: cell phone, keys, wallet, iPod, digital camera, lighter, rolled cigarettes (includes tobacco pouch and papers), pens/pencils, sketchbook, condoms, and space left over for hands to rest
BTW, here's a nice menswear blog: http://theessentialman.tumblr.com/
this is great dave! it's so important to break down the needs and wants plus the innovation...
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