My bosses wife needs a bag - thoughts?

Get her a Longchamp. Not the standard pliage but a overnight bag/holdall in cavass because it's difficult to judge a 40-year-old tastes, LOL and she will definitely use the holdall to the gym, weekend break, etc.
 
Maybe something by Dooney and Bourke... the leather collection? They have some really nice leather bags... try the all-weather leather collection or the Alto line.. very mature, very nice :yes:
 
I obviously don't know her style, but I like both of these Michael by Michael Kors bags and both are right around the $300 mark.
 

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longchamp is a good idea. they have leather bags as well, some of them are very nice, not my style but they are definitely classic and tasteful and i can imagine someone appreciating one as a gift.
 
I agree with Longchamp or MICHAEL Michael Kors - very classic and versatile.

A few other random ideas:

Nordstrom tote, $168.00:


Furla, $185 (also comes in red):
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Kenneth Cole satchel, $228 (also in black, below is espresso):

MICHAEL Michael Kors shopper, $268:

MICHAEL Michael Kors satchel, $298: