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Lovely!

Regrettable in that they just do not look right on me. That being said I do admire a well made or vintage hat for what it is.

The only hats I own are wool or poly watch caps, (I'm an avid backpacker, a must during winter/shoulder season nights and mornings), or a baseball style cap for hiking or outdoor activities where you need to shield the eyes.
 

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^^^^^Regrettable in that they just do not look right on me. That being said I do admire a well made or vintage hat for what it is.

Nonsense, you just haven't found the right hat or the right style of hat.
I had a work colleague who once said " Tom, you've been buying hats for the thirty years that we've worked together and someday, you'll find one that looks good" We're still friends but I do understand the difficulty in finding the right one.
 

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Hat related: Does anyone have thoughts on wearing a bucket hat with a sport coat? As the years fly by and disappear into memory, so does my hair. This has meant a steady increase in hat interest for me.

I just don’t look right in a fedora but I can make bucket hats work. I’d like to be able to dress them up a bit.
 

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Hat related: Does anyone have thoughts on wearing a bucket hat with a sport coat? As the years fly by and disappear into memory, so does my hair. This has meant a steady increase in hat interest for me.

I just don't look right in a fedora but I can make bucket hats work. I'd like to be able to dress them up a bit.
I don't think I could pull that off, and I think that looks better with a milsurp vintage look.

With that said, I did find an article that showed many people that surprisingly pulled it off.

 

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From AAAC

When To Remove Hats
There are a few proper times and places where you should remove your hat. Some of these rules have practical reasons while some others are steeped in history and have been cemented in place as traditional manners.

Additionally, some of the best practices surrounding when to remove hats are seen as a way to show honor or a sign of respect.

Gentlemen should always remove their hats in these situations:

  • When indoors - the history of removing hats indoors started decades ago as a way to remove filthy hats when coming inside the house
  • While eating - it was considered thoughtful to take off a dirty hat when sitting down to eat

Tableware Table Hat Fedora Coat
 

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Hat related: Does anyone have thoughts on wearing a bucket hat with a sport coat? As the years fly by and disappear into memory, so does my hair. This has meant a steady increase in hat interest for me.

I just don't look right in a fedora but I can make bucket hats work. I'd like to be able to dress them up a bit.
I am a fan of bucket hats, but I think they're wholly incompatible with suits.

If you can make bucket hats work, try a trilby: it's less "brimmy" than a fedora, and in a way has a bit of a bucket hat's silhouette (a bucket hat is basically a cone with the point lopped off, and a trilby sort of maps to a cone, albeit with a bit of brim.)

DH
 

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There is a hat out there for every one, just need to find it. I can't go outside with a hat, or cap. I've got a nice selection of tweed caps, my preference being a bond cap. I've also got two Stetson type hats. I'm planning on adding a deerstalker cap, for outdoor pursuits only, in the near future.

Tis is my most recent addition to my collection. This was an ebay thrift, and for being under $40, is of excellent quality and construction. Anyone who is on the fence about hat wear, and considering if it was right for them may want to check eBay rather than making a bigger investment while testing the waters.

F27C9FBC-42AF-421A-88D6-9BB103845248.jpeg
 

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^^^^^^^As I said, find the right style and there is a hat for everyone. Looks smashing Flairball.
JJHatters in NY have been running almost back to back sales, no doubt to try and recover from lockdown.

I've done my share to support them during these trying times in so much as I did not need another hat, but, I try do my part, what's one more hat to add to my collection of over 100 . Many others trying to survive and I have tried to help some of them as well.
I have no affiliation with any vendors.

So to those on the fence, no better time to take the plunge. Flairball proved my theory.
 

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I am a fan of bucket hats, but I think they're wholly incompatible with suits.

If you can make bucket hats work, try a trilby: it's less "brimmy" than a fedora, and in a way has a bit of a bucket hat's silhouette (a bucket hat is basically a cone with the point lopped off, and a trilby sort of maps to a cone, albeit with a bit of brim.)

DH
A bucket hat with a business suit would be tough to pull off, but a casual suit could work. A sport coat and bucket could definitely work. It's really going to depend on specific coat and hat.
 
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