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I'm looking into buying some hats to wear this winter.
I know that you want the hat to be the same color (or at least coordinate) as your overcoat, or the same with your suit coat/ sport coat (sans overcoat). Would this plaid hat clash with a subtle herringbone overcoat?
Also, would you wear a charcoal hat with a navy coat or vice versa?
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And a neutral grey goes with anything. Checked, herringbone, plaid, it doesn't matter. Just coordinate as best you can.
 

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I don’t consider coordinating things like that flat cap at all.

As to fedoras, I wear my black one with dark blue, grey, or black suit, one of my grey ones with grey suits, and one of my brown ones with brown or green suits or jackets, which mostly does coincide with my overcast color if I wear one.

Charcoal with blue would be good just not what I usually do.
 

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I do coordinate my flat caps, but I'm not overly particular about it. So long as the cap is broadly complimentary to the outfit, that's good enough. I'd probably avoid wearing a cap that EXACTLY matches the coat, because a little contrast is a good thing.
 

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I don't think there are any hard and fast rules. Heck, most people don't even bother to wear any type of head covering. The fact that I'm challenged in the follicle department makes it essential.

I tend to wear a hat (either flat cap or fedora, depending on the expected wind conditions) that is in the same color family as my overcoat. For example, a navy hat with a navy coat, a gray hat with a gray coat and a taupe hat with a tan camel hair coat. With a navy suit, I'll wear a gray hat and coat, with a gray suit, a navy hat and coat and with a brown suit, the taupe hat and tan coat. I've been thinking of changing things up a bit and wearing a hat in the same color family as the suit while wearing the contrasting coat.
 

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I’m with Roger on this one.

With flat caps that are solid or herringbone, I’ll have them compliment or be similar to my overcoat. Grey cap with grey, navy, charcoal or Loden coats. Black with grey, charcoal or Loden. Navy cap with navy, or grey. Camel cap with camel hair, beige, brown tweed, or Loden.

All my other caps are tweed patterns. With those I want to have the main color compliment or match the coat. If I wear a cap where the main color contrasts the coat, then I’ll want a secondary color to pretty much match the coat to tie it together and smooth out the contrast.

I do prefer contrast and complimentation to matching, but find that works with solid colors for my navy and tan overcoats and caps.
 

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I'm looking into buying some hats to wear this winter.
I know that you want the hat to be the same color (or at least coordinate) as your overcoat, or the same with your suit coat/ sport coat (sans overcoat). Would this plaid hat clash with a subtle herringbone overcoat?
Also, would you wear a charcoal hat with a navy coat or vice versa?
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They're both handsome articles, and you could wear them with no problem. Though I'd prefer a cap that compliments rather than matches, and a plain weave rather than patterned. Grey or fawn would work nicely.

I do coordinate my flat caps, but I'm not overly particular about it. So long as the cap is broadly complimentary to the outfit, that's good enough. I'd probably avoid wearing a cap that EXACTLY matches the coat, because a little contrast is a good thing.
+1.

Do you all think a herringbone cap with a herringbone jacket is too matchy and should be avoided? This has been concerning me a lot lately.
Likely, yes.
 

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Do you all think a herringbone cap with a herringbone jacket is too matchy and should be avoided? This has been concerning me a lot lately.
There's quite a lot of variation in herringbone so they don't have to be matchy. On the other hand, it is possible to overthink this sort of thing.
 

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Patch work is called patch work for a reason. And it was made obsolute by the industrial revolution. Reincarnations of certain patch work items begrudingly exist because they once did. But not even Fagin's crew ever wore a patch work flat cap. I tried to tell my mom similar in the 50s when she brought an Early American style pole lamp home from Sears. You don't want that cap.
 

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Several years back I purchased and proudly wore a patchwork flat cap. It was more of the brown and green tween pattern, but it was basically the same structural design as the one purchased by Jeff84. Frankly, I thought it looked pretty spiffy and it kept my head warm, when such was necessary. I received more than just a few compliments when sporting that hat. Alas, it was one one many sartorial casualties of the 'Great Purge of 2015,' in preparation of our move to the deep South! ;)
 

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Personally, I think patchwork is supposed to go on a quilt. Along with Peaky and momsdoc, I wouldn't wear one of those, either. But many of the membership don't share my delight in color and pocket squares so who am I to criticize?
 

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I own several flat caps but no patchwork variations. Not because I think they are unattractive or some kind of offensive historical outrage. They're just not "me". By no means would I look askance at an otherwise well put-together gent who chose to wear one.
 
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