Newbie needs help with commuting bags

[samaram]

I understand your dilemma really well. I'm also really well-endowed, and a lot of bags seemed to be designed for boys (i.e. double-shouldered backpacks, where the stabilizing clip that keep the straps together always seems to sit front and center right on top of the girls!!). I haven't had experience with panniers, but, echoing Tulip, don't write off messenger bags too soon either!

My favorite is a bag with a padded strap that has a cross-body stabilizer, like the Timbuk2 Classic Messenger. The padded strap goes down the middle, and the cross strap goes underneath "Righty." DH has a Chrome Metropolis (large classic messenger shape), and that cross strap fits right at his armpit, so I would probably avoid that one, but I would die without my Timbuk2. The volume on messengers is expandable, versus the static dimensions of a traditional backpack or panniers, and it shapes to fit your body so you can always shift things around to find a comfortable spot.

Here's me home from work. Contents of the day are 1) remains of lunch--one small and two medium-sized Tupps, 2) saddle I bought off Craig's List, 3) work shoes--flats, 4) work clothes, 5) 2 textbooks, and 6) the usual junk:my wallet, graphing calculator, 3 lights, jewellery, and tire levers, spare tube and handpump. Would that fit your bill? Plenty of room for more!