Being bald is a great excuse to get creative with hats. To switch up an entire outfit's style, all you have to do it switch from a fedora to a fidel cap, or from a beanie to a trucker hat. I enjoy the freedom of choosing hats without worrying about "will it mess up my hair?" or "how will my hair look sticking out from underneath it?" Of course, throwing any kind of protection on a bald head will keep you warm in the winter, and away from sunburn in the summer.

So here's the question:
How does one casually and confidently pull off the "hat look" without it seeming like they're just trying to cover up their baldness?

I'm sure some people would think "oh, he just wears hats because he's bald and can't accept it," when they should be saying "damn, this guy's got style!"

Please discuss.

I really like hats and wear a hat almost all the time in cold weather and a lot of the time when I am outside exposed to the sun for significant lengths of time in warmer weather.

I do not ever want people to think I am hiding my bald head so I am sure to always remove my hat indoors. I see a lot of men wearing ball caps while eating in restaurants, sitting in movie theaters, etc. That, to me, is either trying to hide a bald head, messy or dirty hair, or is just simply impolite.

I also like to expose my head to some sun so my head matches my face so I do go outside without the hat for short amounts of time. People don't get the impression I am hiding.

I see a lot of men wearing ball caps while eating in restaurants, sitting in movie theaters, etc. That, to me, is either trying to hide a bald head, messy or dirty hair, or is just simply impolite.

It's a lack of manners and very impolite

I agree with the hats.  From my motorcycle helmet to a baseball cap, winter toques, or whatever else I feel like wearing there is always a fear of removing the hat and have the most unacceptable hair underneath it.  With the shaved look clearly this isn't much of a concern.

I think what the guys said about people who wear hats all the time are correct, that shows an insecurity about baldness. Getting creative with different types of hats and in the different types of weather I don't think really counts in this sense, and yeah some people may think you are trying to hide a bald head, but if it is cleanly shaven no matter what people will know you have dealt with it in the most masculine and mature fashion possible.

I love fedoras for instance, and they tend to keep a hairstyle reasonably intact within, but am very much looking forward to being able to slap those and the irish style caps on my head without any fear of the underlying hairstyle in the not so distant future.  I am also rigorously hitting the gym daily now so sooner or later people will just assume its part of the muscle freak look (although I am not going to let myself get that big).

Cowboy hats?  Hahahaha, can't wait

Ive been known to rock a cowboy hat on occasion

I never liked wearing hats when I had hair... and that hasn't changed.. . but it's a case of having to in the winter, I usually wear a beany type hat, and it comes off as soon as I'm in doors, never wear one in summer, just sunblock and a smug smile lol

I wear hats a lot,

A.  I fuggin hate being bald

B.  No matter what kind of sun screen I use, the sh*t drips down into my eyes, when I sweat, and I sweat a lot, then my eyes get red and swell shut.... hypoalergenic whatever it doesnt matter.

I used to wear hats alot when I had hair.  No one ever accused me of hiding my bald head, mainly because my hats went with the clothes that I wore, be it a fedora when dressed up, or a Kangol or newsboy cap when going out on the town, or a ball cap when dressed casually.  To me the hat completed the outfit....and I had quite an extensive collection of them.

Now that I've shaved my head, I rarely wear hats.  Not because I can't, but because I feel that the bald and bearded look just goes so much better with anything that I wear from formal to casual.  If I do wear a hat it's typically my snapback ballcap worn backwards over the bandana that I'm wearing.

And I have to address the wearing the hats indoors.  To me, it's a sign of changing times.  I don't find it rude, impolite, or a lack of manners.  Many guys today wear hats to match their outfits, as I mentioned I did.  Or they wear it because they had to run of the house and didn't have time to shower, or simply because they didn't want to have to deal with their hair...could be any number of reasons.  Hats today are as much a fashion statement as the shoes on our feet, they're not worn for pure functionality anymore.

I never took off my hat once I had it on, whether it was indoors at the mall, the club, the restaurant, the movie theater, etc.  Two reasons, 1) It's part of the outfit that I am wearing out and completes the out, and 2) Why would I want to show the hat head that I have once I take off the hat?  That would totally defeat the purpose of looking put together and make me self-conscious that this perfectly fine get-up has been ruined by hat hair.  No one want to have to deal with hat hair. 

And to be quite honest, as was mentioned earlier, you have to own it when wearing a hat.  Not all hats look good on everyone, when you wear one that you like/enjoy wearing, own it, and look confident wearing it.