STYLETHREAD -- LET'S TALK SHOP!

i have had this bag for a few years, and i like it, but i only really carry it when i am traveling because it is so big.  do you guys honestly think it is still in style and would it be ok to start carrying it on regular days? what could i wear it with?

http://cgi.ebay.com/ws/eBayISAPI.dll?ViewItem&category=63852&item=6740737330&rd=1

it looks really dark in this pic--it's the "saddle" color that they always have.  and this ebay seller is a big fat liar because the bag was a special edition that was never sold in stores--they had it with gold hardware but not silver. 

anyway-second question: my mom got me the little wristlet that they had for x-mas that is the wavy bright-colored suede stripes (i think some people here posted the matching tote--maybe it was Karina?)--i'll try to find a pic to post.  anyway, i like it but i'm not sure what to wear it with--any ideas?