I picked up this vintage Coach bag on Ebay a couple years ago, even before the new Coach Classic bags were out. I love how simple and timeless this bag is, and how it works equally well with jeans and a professional outfit. I’ve used the bag with a dress for the evening (held onto the top handle) and thrown on cross body along with jeans and a flannel. The latter is probably my favorite look, I love a structured boxy bag with a casual outfit. A bag like this can make a sloppy outfit look put together for my morning coffee run.

I’m on a hunt for my next vintage Coach, which I am hoping will be a large duffle bag in a broken in tan leather (similar new bag here).