My most daring purchase was my Manhattan GM. I went to the store only to "look" and ended up buying it and having to stuff my alma in my much too small suitcase I travelled with (to ensure I didn't buy the GM). I still am shocked sometimes that I spent so much that day.
When I bought the Cabas globe shopper I wasn't sure I would ever use it but I ended up loving it and hardly using other bags the rest of winter. I still love it.