The Private Practice star keeps it simple at the Kentucky Derby with a basic black fedora.
The duchess looks spectacular in a simple cream floral confection at Zara Phillips' wedding.
The sports reporter chose this feminine feathery hat for the 2011 Kentucky Derby.
Known for probably the most-talked about hat at Prince William and Kate Middleton's wedding, the princess goes a little more tame this time around.
The actor chose to switch up his style a little bit wearing this checkered cap.
The model chose some rather delicate headwear for her visit to the Kentucky Derby.
The royal opts for a more whimsical look in this floppy topper.
The TV host keeps things lively at the 2011 Kentucky Derby.
It's hard to tell how her feathered brown hat stays on.
The stars pose on the red carpet at the Kentucky Derby.
The duchess really likes her flowers! This is the second time she has donned a hat (if you can even consider it that) made of flowers.
The Modern Family star goes all-out with her derby hat.
The football star played it cool with his subdued derby hat.
Beatrice wears a butterfly nest to the wedding of Autumn Kelly and Peter Phillips in 2008. The designer: Philip Treacy, the favorite miliner for royals the world over.
Actually, we have no idea whether the duchess's hat can field signals from space. But it sure is chic.
The mother of eight opted for a very frilly hat when she attended the Kentucky Derby.
The duchess wore this wheaty creation for her wedding to Prince Charles back in 2005.
The Celebrity Apprentice star goes for a black-and-white ensemble at the Fillies & Stallions Derby in 2011.
This hat may or may not have been made of fondant from Paris Hilton's birthday cake. We'll get back to you.
Vanessa rocks a little black hat while Nick opts to go bare.
Princess Anne's daughter chose this hat for a rainy trip to the Royal Ascot in 2007.
Jordin Sparks is pretty in her pink hat at the Kentucky Derby Winner's Party.
Prince Edward's wife walks on the wild side with this topper.
The queen attends the 2010 Royal Ascot, of course, where royals and amazing headgear mix.