I definitely would recommend anything in the legacy collection in leather. I personally have an Ali in whiskey and I love the way it looks. The strap is a bit thick so sometimes it slips off my shoulder, but not very often. The slim tote that was recommended also looks great.
If not one of those, I actually have come to like the ergo stuff. I love the ergo large totes, or if you can I would go for the vintage leather ergo travel tote. It's the $548 one that I got today. I like the look of the leather on that one better than the camel.
Accessories-wise I would say anything legacy striped, that seems to be super popular. The watercolor oblong scarf is BEAUTIFUL, so if you think you'd wear it at all I would go for that.
You can't go wrong with sunglasses, and I know I feel really chic when I wear mine, so maybe go into a boutique and try some on, and find a pair that suit you to get.
I would say definitely get some kind of charm to hang off your bag. Depending on your personal style, maybe get a zodiac one (I adore all things astrological) or an initial charm. If you think you'd like it, get the skull charm. I have one, and I love it because it's pirate-y and also seems unusual for
Coach, so it's different.
Whatever you end up with, please let us know. Happy upcoming Birthday!