Ok, so I'm not the most stylish of people, but I don't like looking like an idiot either.  I match my shoes and my belts, my socks to my pants, and I try to keep my fly zipped (in public anyway).

 

I have a very nice black fedora with that I would like to wear more often, but it just seems so formal.  It's a shame, because outside of special occasions, I don't have much opportunity to dress up.

 

Also, I've looked but I can't find any rules that say your hat should match anything else.  Are there rules? What are the rules? Should it match the coat?  What if you're not wearing a coat?  Are there any black/brown rules that apply? 

 

Why is is so hard to wear a hat these days?

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Just asked this in the hat group, hopefully it helps.

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Thanks!
Grey is most versatile.

Black, Brown, Navy also excellent.

No need to have it match your coat - but that's why grey is superior, as it matches everything.

Personally, I have only a black fedora and a navy trilby. I wear the trilby with my navy DB overcoat and the black hat with all else.

For casual wear, I have a tweed jeffcap I wear with a brown moleskin overcoat.
No real rules. Only a few personal preferences. I don't try to match my hat with my coat because it looks like I'm trying too hard to some people. There's nothing wrong with wearing a black fedora in public outside of a formal occasion (although people might think you're Jewish).
Especially if you're wearing the Hassid hairstyle that's all the rage these days.
Technically, black should be OK with most everything, but I personally try to match things more closely, depending upon whatever suit or sport jacket/slacks combo I am wearing.

I have a black fedora and a brown fedora, so if I am wearing black or gray tones, I wear the black one, and if I am wearing tans/browns/greens, I wear the brown one. My overcoat is brown, but I match the hat to the suit/sport coat I am wearing underneath.

Hoping to add a nice tan one to my rotation soon as well!
Just as an afterthought, back in the days of yore, a man had at least two hats. One hat for day-to-day work and one formal hat. I think that hats are better matched to purpose than to wardrobe. You save yourself the trouble of having to wear a worn down hat to a formal event and not worry about messing up an expensive one during the day.
In the movies from the 30's and 40's, the men's hats tend to be a sort of taupe color or a medium gray.
Exceptions for formal, summer straw, or military covers of course.
No. Black is winter and white is spring/summer.
"Personally, I'd focus on matching the level of dressiness or formality more than the color."

If they are all fedoras, how do you determine "formality"? Doesn't seem to make sense.

I wear mine more in winter to keep my head warm without wearing a stupid stocking cap. Black fedora with my grays, blues and black suits/coats. Brown with my darker earth tones, and the pecan (lighter tan) with my lighter earth tones.

Probably will get a white panama for the summer, though. The "rule" was there for a reason, after all. Much cooler that way.
Makes much more sense!

Mine are all wool felt, so I wasn't considering material. Though for summer, straw is much better.

As far as formality, I tend to think style. Fedoras tend to be more formal (coat and tie, or at least a brown leather jacket and whip!), whereas if I am less dressed, I will throw on one of my Ivy caps instead.

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