How to Get Your Derby Hat to Kentucky

Events / Travel
Hats are a must for the Derby, but transporting them can be tricky. (Eclipse Sportswire)

So you’ve found the perfect hat for the Kentucky Derby. Now there’s only one challenge: How do you get your Derby day hat to Louisville?

Without a car or a private jet, transporting those voluminous toppers takes careful planning. The good news is the advice is simple.

It starts with ruling out what will only cause headaches: carrying a hat box onboard a commercial flight. Flight attendants won’t kick you off the plane for doing it, but as you shove your round hat box into a square compartment, you see some evil eye.

Worse, you’ll probably crush the fancy hat box, potentially endangering the hat.

There are two good options, though, and both include good old-fashioned cardboard boxes.

First, if you want to travel with your hat, treat it like cargo: Bring it to the airport tightly packed in a cardboard box, which will be headed for the cargo hold.

“Cargo goes on a different conveyer belt than the luggage,” said New York-based milliner Christine Moore. “So it may come out the same carousel, but it goes in two different processes.”

A Derby hat on the red carpet. (Eclipse Sportswire)

When treated as cargo, boxes can be stacked with others, as opposed to thrown into the luggage jumble. And it has worked many times for Moore: “I have never had a crushed box.”

But if you have the time to plan ahead, the easier option is to pack your hat and ship it directly to your hotel or your host’s home.

Moore ships hats around the world daily and recommends UPS.

Milliner Lisa Carey, whose label LD Carey is based in New York, finds UPS can be more expensive than other shippers, and DHL can be difficult to find in some locations.

“FedEx Ground can typically have your hat in Louisville from anywhere within the U.S. within four to five business days at a rate of under $30,” Carey said.

She advises labeling the box with your name, your cell phone number and the name that the reservation is under at the hotel. While Louisville hotels are accustomed to this process, they do receive hundreds of packages daily, so any help you can give them will ensure your hat arrives on time.

As for what goes in the box, if you’ve just bought your Derby day hat, the shop can probably pack it for you. But a few pro tricks will keep it in shape if you are in charge.

“If you must pack your hat yourself,” said Carey, “fill the crown lightly with tissue and roll loose cylinders of tissue to place around and under the brim to support it.  Pack the corners of the box with tissue to hold it in place during shipment.”

The same advice holds if you have a hat that can be packed in your luggage. “You can roll your clothes around your hat in your luggage,” said Moore, advising on a tight pack. “The thing that crushes a hat is the movement.”

For fascinators, just follow the contour of the decoration and make sure it is supported. “You want to support the shape and not have movement,” said Moore.

However you plan to travel, just eliminate the thought that you’re going to step off a commercial flight looking like Grace Kelly, swinging a glamorous hat box. If you brought it onboard, that box is probably going to take a beating.

Says Moore, “The hat is more durable than the hat box.”

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