If I didn't have a ridiculous number of bags on my mind already, I might add this Jack Spade Waxwear Utility Bag ($425) to the list as well. Sure, it's made for men, but the luscious wax-woven (and waterproof) cotton in that beautiful green color is right up my alley.
It's perfect for dad, but totally acceptable to give to your brother, husband, uncle, or whoever you want to splurge for this Father's Day. The inner zippered compartment can hold a laptop and files for the busy guy on the go, and the two expandable outer pockets will have him finding a home for his phone, iPod, and keys. Ridiculously expensive? Sure. But totally crave-worthy? Oh yes, indeed.