How to select the perfect travel hat

Question

I'm on the quest for a perfect travel hat. My requirements, in order of priority:

1. Sun protection. I'm balding. I don't like sunscreen.
2. Should not have an overly stiff brim that gets in the way taking portrait-orientation photographs.
3. It should travel well.
4. It shouldn't make me look like a doofus. I know "doofus" isn't a very precise term. And what looks good in one region may look doofusy(?) in another.

In the past I have tried:

• Baseball cap. Fails #2 and #4. And isn't great for #1, since the brim only keeps sun out of my eyes, and not off my neck/shoulders.

• A "fishing" hat. Works for #1-3, but fails #4. I don't feel self-conscious wearing this hat when I'm traveling the U.S. in a T-shirt and shorts, but in other parts of the world I prefer to dress a little nicer (long pants, button-down travel shirt), and then the hat looks really out of place.

Some research came upon the concept of a foldable panama hat, which really appealed to me because it's classy, but also casual enough to wear when I'm not at a formal event or whatever. The foldability makes it ideal for travel, where I don't want to wear a hat all the time (in a bus, on a plane, etc).

However, advice from Brent Black at The Panama Hat Company is not to fold/roll your panama hat:

...you can’t realistically expect any natural straw hat to look as nice after it’s been rolled as before.

People often compare fine Montecristi Panama hats with linen. Okay, let’s suppose you pick up your linen suit from the cleaners. You take your crisply pressed suit home, roll it up, and pack it in a suitcase. You jet off to your private island. You unpack. You and I both know that suit isn’t going to look like it did before it went into the suitcase. Same with a hat. And as with the suit, a little steam directed at the rumpled parts should spruce it up. (source)

So I'm left trying to find the perfect balance between portability, and fashion.

What should I look for in a hat that will travel well?

Or am I better off getting a nice hat, and just making sure I never crush it? Is this even practical when traveling light? (I will not be carrying a hatbox with me!)

Or perhaps the foldable Panama hat really is a good solution, and I should just accept that after rolling it a while, it just won't look as good--but will still probably look way better than a baseball cap or fishing hat.

Answer 1

If price is no object, then you really need to look at Tilley Hats.

They are basically an institution amongst those that own them, and have definitely been designed with at least most of your criteria in mind.

I don't own one, and am not enough of a hat person to be able to bring myself to spend ~US$80 on one, but having met people who have owned them I can definitely see the fascination with them - especially when it comes to travel. Google will find you countless reviews, and you'll have to look hard for one that isn't favorable.

Answer 2

(A few years late, but) My favourite travelling hats are these squashy hats that roll up into a supplied bag, with a sprung coil around the edge, made of suede, leather, kangaroo or canvas, by Barmah of Australia.

I think this UK distributor has a better website than the manufacturer. Prices are something like £33 (canvas), £40-50 (leather), £65 (kangaroo).

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Yes, they have a bit of the "Crocodile Dundee" about them, but it's an authentic look. Apparently I have the "1025 Suede Hickory". It has been used in the Outback, during Indian monsoons, up mountains and volcanoes, and picked up some wear but I think it's only looking better with age.