“Grab your coat and get your hat / Leave your worries on the doorstep / Life can be so sweet / On the sunny side of the street.”

Ella Fitzgerald and Frank Sinatra each famously sang “On the Sunny Side of the Street,” and they had another thing in common: They both wore hats. Perhaps that’s why their side of the street was so sunny?

Let’s face it: There’s just something about wearing a crackerjack hat and the smiles you get from folks who are thinking, “Wow, I wish I had the confidence to wear one.” Especially now that they’re all the rage, with everyone from George Clooney to Johnny Depp sporting cool lids. Recently an incognito Brad Pitt flew into LAX wearing a dark burgundy velvet fedora with the numeral 5 on the side. Très cool. Reminds me of the flamboyant styles at Anthony Peto in Paris.

But if Spendy Wendy were going to drop some coin on her man, she’d think Big Ben and go with this wool houndstooth fedora with a black leather band by London Fog. It’s classic, but current, and costs a cool $52.50. It also comes in brown houndstooth check—why not buy two?

Packing Tip: Don’t even think about cramming it into your bag. Pack it on your head, and then you don’t have to worry about bad hair days (guys have them, too!). For gals, I’d say wear it if you can, but if it’s more of a formal hat with a wide brim, then consider shipping it ahead. Or you could devote one piece of luggage to it, and pack lots of tissue in the crown and on all sides, so it doesn’t lose its shape. Me? I’d never consider buying a hat unless it’s crushable or “packable”—a style many top designers are sensibly adopting, even Eric Javitz.

To check out another awesome lid— J. Peterman’s Owner’s Hat—turn to the “Mode:Road” section in the November issue of Sky.

Have you tried packing a hat? Share your tips!

Wendy
Delta Sky