I am very much drawn to the straw panamas. They seem very "American abroad," but in a positive, old school sort of way.

But I am horrendously bad at matching hats with faces. I know that I also have a round face, and what seems to work for me is hats with large brims (they seem to balance me out), so I'm guessing a panama hat would work.

(Just don't wear one of these in Venice -- people will ask you to row their gondolas!)

Oh, occhiblu, you are such a hoot! heheh
Also, I do like the look of that putty panama.

:-)

I would also point out that, in Italy and I suspect in much of Europe, "fashionable" often means "correct and expected," as opposed to "unusual and unique," if that makes sense. So if you really want a fedora, I wouldn't not get one just because you think it's too common.

Easy. Pith helmet.

For those coffee shop safaris in Amsterdam perhaps?

I have been looking at some of the more modern cut fedoras.

Y'know, ever since this thread appeared on the front page, I've had this song running through my head. I realize that this is probably not terribly helpful, but you must admit that it is a pretty cool song.

"Pith helmet." that made me LOL

I don't know why baseball hats are out for you, but they're pretty ubiquitous worldwide.
Beanies are very fashionable, but I don't think you'll be able to pull the wearing of one off.
Maybe something in an Australian style would be best.
I don't really know though.

I would go for a Panama hat. I think you need a hat with a brim to balance your features. And a real Panama hat rolls up into a tiny tube for easy packing.

If you dress well you can get away with practically any hat around here. I'm partial to the Kojak hat or the newer stetson andes

Try the Greek Fisherman's cap - you might love it. I actually think it looks much better on older or heavier guys than slim young men, who just can't seem to carry it off without looking sort fake "leather-queeny". At any rate, no need to pick only one (just ask languagehat!); get two or three you like, and maybe one will end up feeling totally "you", or maybe you'll just switch for different climate conditions and moods.

Also, I very much like Van Morrison in this:

≡ Click to see image ≡

You might want to see how you look in something similar.

What I like about it ^: it's not "dimpled" (I have no idea what this is actually called, but, like, fedoras have those indents? that thing.); the ribbon is very minimal, not too thick, not shiny. Round brim, not very wide; crown is not too high. Black.

Actually, okay. I'm just going to marry the hat, alright?

Hats are not particularly in fashion in sourthern Germany right now, but you can't really go wrong with a fedora anywhere. But rather than worrying about the fashionability when you're shopping for a hat, just think "Does this make me look classy?" and if the answer is "yes", then go for it.

Here in Munich I've seen a fair number of women and men wearing fedoras and other classic hats; I've also seen a ridiculous number of Yankees baseball caps on native Germans, which never ceases to confuse me. I wouldn't say that hats in general are particularly fashionable here (beyond old men wearing full tracht), but no one will look askance at you for wearing one. If it looks good on you and matches your general style, go for it.

I agree that baseball caps, berets and Stetsons wouldn't suit you. A fedora or panama would be a good pick. You'll probably have to just go to a shop and try some on to get an idea of what will look good, and to be sized, and then armed with that info you can either buy at the shop or online. And don't worry about fashion. Aim for style, and style means wearing what suits you.

Thanks, guys; great suggestions! I only want one right now because I plan to take no more than a carry=on for my two weeks in Europe. Most of the clothes I am taking for the cruise part are getting too big, so I will dump them at the local version of Goodwill in Genoa.

I've also seen a ridiculous number of Yankees baseball caps on native Germans, which never ceases to confuse me.

The Yankees thing is popular with teenagers here in Nuremberg, as well, but what really throws me off is native Germans wearing sports apparel from less well known American teams like Green Bay Packers jackets and Florida Panthers shirts.

I really do like the straw Panama idea for summer.

The bigger, wide-brimmed hats (fedoras, panamas, trilbies, etc...) are ideal for big, masculine, mature fellows. Younger, slender guys with delicate features / thin faces should try a newsboy cap, beret or messenger cap.

nth the Panama hat. Classy. And I think it would suit you really well.

That's a great photo of yourself, Ardiril.

Beware of recommendations for eyewear and hats./ The bottom line is how you feel and can you pull it off and feel totally comfortable. My brotherublaw wears a beret. That's in Missouri and it's just him, no one snickers at all.

I also thought of fedora,
Borsalino Milano Fedora, but for $348.00 .//// Yoiks./
I'm thinking too money...signori, que hora es...I'll take that watch too BTW.

taz, Van's hat looks great, Godfather-y.
This Bali ballcap kills me. OMG, that's sad.

The 'wheely' ought to be called The Chairman, looks cool, but not for Ardiril...
Big It Up always have up to date hats....your 'wheely' is their Castro Camillo.
The Big it Up Homburg looks cool, except it's fur felt.
Your 'deerstalker', that's a Sherlock Holmes... maybe Kangol's Tweed Bugatti

Good gorsh, hats for gentlemen...ouch.