Tip #4 when buying a hat:
"Try to buy your hat for a specific costume or wardrobe. And when you are buying it, try to have the costume either on, at at least with you. The hat that sits in your closet is the hat that you can't afford. Charm is reason enough for buying a hat, but if it can make itself socially agreeable to your clothes - so much the better!"
Again, this rule applies to all accessory purchases. You may love it, but does it work with the rest of your wardrobe? It is better to buy one hat that you can wear with multiple outfits, than to buy one hat and then have to buy a new outfit to go with it.
As an example, the wonderful gold sweater with matching turban above by Florence Reichman makes a stylish set. But can she really wear the turban with other items in her wardrobe? Probably not.
How much more practical and versatile are these fedoras from Dobbs? Still fashionable, yet they would probably work with many more items hanging in your closet.