I vote for the bowler!
I just bought a necklace very similar to the Tiffany one you are interested in, except it's made of sterling silver, has three charms instead of two (key, engagement ring, and heart), and instead of diamonds, the engagement ring and heart charms have sapphires. The three charms are supposed to represent truth, wisdom, eternity. It's from Links of London, which is comparable to Tiffany and it cost around $250. With that price, you can pick up the necklace and bag!