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Recommend me a good starter hat

I do not know if this a by product of recently converting to DE wet shaving, but I seem to have found a renewed sense of classic style. I am enjoying the look and feel of good shave, I want to translate that in to how I dress. I recently aquired a 3/4 length Black Wool coat that the weather should allow me to show off in the next week or so. I want a nice hat to complement the coat and provide some protection from the brutal winter that I will be facing walking the streets of downtown Chicago. While I have always liked dress hats, I have never taken the chance and picked one up. Now I think I am ready to take the plunge. I am thinking of something in the neighborhood of $20-$30 and then if I decide I really like it I can spend the money on higher quality hat.

Any suggestions?
 
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Check out your local thrift store/salvation army.
It will probably net you a high quality hat at a low price, often cheap hats look and feel like cheap hats. I've gotten several very high quality hats for $10-$20 at the thrift store. Nearly new too. I think (morosely) that since not many young people wear hats anymore these hats probably belonged to an elderly gentleman who wore them for special occasions and no one in the family knew what to do with them when he passed so they got shipped of to goodwill.

That said, I don't wear hats anymore, but I maintain that a cheap good hat will look better than a cheap bad hat.
 
Excellent quantum leap...if you are in Chicago you must pass by Optimo Hats to see what means hat good taste. Graham Thompson, the owner, made the Public Enemies movie hats...Of course, forget about 30/40 bucks for a hat...just add an extra zero 40(0) and you're served!!:wink2:

If you have a black coat, please, do not buy a black hat but a grey one or brown. Fedora maybe to begin?
 

Thanks for the link. There looks like there is some good stuff there.

If you have a black coat, please, do not buy a black hat but a grey one or brown. Fedora maybe to begin?

This is exactly the type of advice I I was looking for. I was originally thinking of something either brown or a darker grey.

In Septemeber, I was in Traverse City, MI and we walked into the hat shop along the downtown strip and that was one of the things that got me interested in finally breaking down and finding one I liked.
 
Well, you can wear a black hat of course...

[YOUTUBE]http://www.youtube.com/watch?v=KxxuSiC4wNw[/YOUTUBE]
 
+1 on checking out the local thrift store for some. I see a ton of well-preserved, old-style men's hats there. They're usually scattered all across the top of the racks, and rarely exceed $10 in the places I've seen them.
 
What do you want the hat to do? A gray or conservative plaid or tweed flat cap might make subdued fashion statement while keeping your head warm, a stingy fedora might declare you to be a hipster, a thin ribboned fedora or outback hat might give a country flavor, etc.

Here's a guidethat gives tips on how to pick a hat to suit your face.
 
What do you want the hat to do? A gray or conservative plaid or tweed flat cap might make subdued fashion statement while keeping your head warm, a stingy fedora might declare you to be a hipster, a thin ribboned fedora or outback hat might give a country flavor, etc.

Here's a guidethat gives tips on how to pick a hat to suit your face.

Hmm. According to your site, I should be wearing a Bowler or Homburg. I don't know that anyone can pull either off without looking ridiculous.
 
The question -IMO- is the equivalent of a woman picking out a dress (in no way am I poking fun, just trying to draw an analogy); what meets the needs and expectations and satisfies (and also looks great on) that someone may be completely unsuitable for another....Personal preference, body type -head shape- etc... all come into play.


That said; I'm a bit partial to the bogey hats, if I were to ever wear a gentleman's dress hat....best of luck, mate!
 
Hmm. According to your site, I should be wearing a Bowler or Homburg. I don't know that anyone can pull either off without looking ridiculous.

Nah, just guidelines, and the Homburg or Bowler might well be way too much, they would be for me! You could get the same effect with a Fedora with modest taper and a full brim. Grey and brown are good conservative choices that go with a lot of colors.
 
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