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Recommend me a good starter hat

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.

I have a prominent lantern jaw and square face, so your site suggests a round crown and brim (thus the bowler or Homburg). Funny though, the historical examples of folks that have worn either don't seem to fit that description.

Neither Stan Laurel or Oliver Hardy (Bowler) had square faces and neither did Winston Churchill (Homburg).
 
Here ya go

Wrong, that's a New Era hat!


Here's a Starter hat:

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I went to a couple of stores after work and found one of these Country Gentlemen hats.

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Even though the price was right, I didn't pick it up. There were a couple flat caps I was looking at too. I am going to drag the better half out with me on Sat to make sure I am not deluding myself.
 
+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.

I went thrifting today. Three Thrift store zero Hats. Maybe I need to hit more Thrift Stores near the urban core?
 
As a member of the Fedora Lounge, I want to talk you out of a $30 hat. New, anyway.

If you want to start low, go to theFedoraLounge.com and poke around in the classifieds. You'll need to know your hat size (which isn't the same as your fitted baseball cap size).

There are a lot of vintage hats that can be had for not too much, and you'll be better served by a felt hat.

Any new hat you find for $30-$40 is going to be wool, and honestly - cheap and cheap looking. Wearing a really cheap hat is going to turn you off. (Imagine if I told you I wanted to get a better shave so I said I was going to buy a Bic disposable to see how I liked using blades.)

You have some good hats stores in Chicago. For ready made hats:

Hats Plus
4706 West Irving Park RD
Chicago, IL 60641-2701
773 286-5577 Phone

I recommend a trip there to try hats on, and find a style you like. Even the inexpensive felt ready mades run higher than you're looking for, but you'll get a sense of what's available. I've had good dealings with them. I'm thinking the style you have in mind is basic fedora 2 1/4 to 2 1/2 inch brim. Bowlers and Homburgs can be cool- but it's kind of "advanced" hat wearing, and would be more confronting to start off with. I only wear my homburg when pretty styled up.

On the south side, you do indeed have the Harley Davidson/Cadillac of hat makers- OPTIMO. Their fedoras start at $550.

I started with hats same as you're trying I guess...I bought an inexpensive one to see if I liked it. It was about $120. Hats are pricier than you think.

Go vintage- check thefedoralounge, or look on eBay for someone selling used contemporary fedoras (Stetson, Dobbs, Biltmore, Bailey).

Hats are not for everybody. It is worthwhile to test it out. If you let the hat wear you, you will get snickered at, teased and mocked. It's a kind of Zen thing- when you shift to wearing the hat, nobody f's with you on it. Rarely anyway. There are always some asshats out there.
 
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I went to a couple of stores after work and found one of these Country Gentlemen hats.

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Even though the price was right, I didn't pick it up. There were a couple flat caps I was looking at too. I am going to drag the better half out with me on Sat to make sure I am not deluding myself.

That's a fine, functional hat.

But if want to show some style and stand out, you need a fedora.

It will be like aftershave with the better half- she's going to love it or veto it fast.
 
As a member of the Fedora Lounge, I want to talk you out of a $30 hat. New, anyway.

If you want to start low, go to theFedoraLounge.com and poke around in the classifieds. You'll need to know your hat size (which isn't the same as your fitted baseball cap size).

There are a lot of vintage hats that can be had for not too much, and you'll be better served by a felt hat.

Any new hat you find for $30-$40 is going to be wool, and honestly - cheap and cheap looking. Wearing a really cheap hat is going to turn you off. (Imagine if I told you I wanted to get a better shave so I said I was going to buy a Bic disposable to see how I liked using blades.)

You have some good hats stores in Chicago. For ready made hats:

Hats Plus
4706 West Irving Park RD
Chicago, IL 60641-2701
773 286-5577 Phone

I recommend a trip there to try hats on, and find a style you like. Even the inexpensive felt ready mades run higher than you're looking for, but you'll get a sense of what's available. I've had good dealings with them. I'm thinking the style you have in mind is basic fedora 2 1/4 to 2 1/2 inch brim. Bowlers and Homburgs can be cool- but it's kind of "advanced" hat wearing, and would be more confronting to start off with. I only wear my homburg when pretty styled up.

On the south side, you do indeed have the Harley Davidson/Cadillac of hat makers- OPTIMO. Their fedoras start at $550.

I started with hats same as you're trying I guess...I bought an inexpensive one to see if I liked it. It was about $120. Hats are pricier than you think.

Go vintage- check thefedoralounge, or look on eBay for someone selling used contemporary fedoras (Stetson, Dobbs, Biltmore, Bailey).

Hats are not for everybody. It is worthwhile to test it out. If you let the hat wear you, you will get snickered at, teased and mocked. It's a kind of Zen thing- when you shift to wearing the hat, nobody f's with you on it. Rarely anyway. There are always some asshats out there.


I understand what you are saying, but for me right now spending anywhere close to $100 on hat is not something I can do right now and still call myself I responsible adult.

I'll definitely be hitting the thrift stores and such looking for something I like. And I was looking at the fedora lounge and I did not see the Classifieds section. Is that something you have to register to see?
 
I hadn't thought about it, but evidently you do have to register to see the classifieds.

I wish it were easier, but I had to speak up much the way you would if I was heading down a bad path in the shaving world.

Luckily, in Chicago, there's a very good chance you can find a thrift or second hand store that might have some pretty good used hats. Finding them might be tricky, since they're not usually web savvy kind of places.
 
I do appreciate the advice. I still have 3 buildings to go through at the antique mall up the street looking for shaving stuff. If I am lucky I might find a cool hat.

I'm definitely going to register at the fedoralounge and take a look at what is out there.
 
Since someone mentioned hats, I would highly recommend this site. Brixton is where I bought my hat. I wasn't much of a hat person until I checked out their site. I ordered the Hooligan and it feels and looks like it was made for me! This is now my go everywhere/ukulele playing hat.:001_smile . Hats are great. They protect the head from the sun and keep your head warm when it's cold. Now I need a black one too!
Ernest

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had great luck with thrift stores. found a like new Saks Fifth Avenue fedora that would fetch over $100 for $12.

love my fedora, but an Irish cap is a nice timeless style that isn't as drastic as a fedora. Hannah is a good brand.
 
jonwings...What size do you wear ? I have a lot of vintage hats.I could part with one.A starter hat is like a starter razor,you can get a great deal on a good one.
 
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