Haven't posted in a while; these days I'm using a spring/summer canvas tote from Calvin Klein Collection. I like that it's simple, minimal, but very sturdy (the canvas is reinforced with leather trim. CK Collection continues to be one of my favorites; I'm curious to see what happens with the brand as they hire new creative directors.
Vintage Chanel PM is lovely, of course. I still think the current is okay, but I agree the older is better.
You can also try the vintage Tiffany for men, which is a very, very close sibling (same nose).
Today I did some old Chanel CdR... stunk up the whole place in true Rach style.