9 Classic Hat Style For Men - Why Wear Mens Hats - How To Buy Men's Headwear

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Love hats. Wish us men all wore the style of the 20's 30's 40's and 50's again.

I wore a bowler hat with a Halloween costume few years ago. Going for a Dr Jekyll look with a bowler hat. After examining myself in it, I thought it really brought out my inner gentleman. I experimented with my look by wearing a cheap costume quality hat. It really added a new element to my look and fast forward a few years I got a legit bowler hat for my birthday. Nothing feels better than going retro classic.

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I like wearing my fedora every day. Hats are functional & practical & I've really taken to wearing a hat so much so that now I wouldn't even think of leaving for work without my fedora. It's a classic men's look & I encourage all men to consider making a hat part of their regular routine. On the weekend I usually wear my panama. It's a lighter & airy choice for here in Arizona especially in warm or hot weather. I think the has you're wearing is a trilby with the brim in the front snapped up.

I own about 20 Trilbys and a dozen bowlers and wear one everyday. I was hooked on these two types about 7 years ago and every suit I own I have a hat that matches it perfectly.

My Grandad is 97 and he's got a massive collection of hats some dating as far as 1930s.

I'm 53 years old and I began wearing a Tilley hat (please see the Tilley website) this past summer to keep the hot sun, and the rain off my head... and I wear it with confidence. I get a lot of looks and comments simply because most men will only wear baseball caps, but I've never received any criticism so far. Thank you for all your great advice, my confidence had been lost for far too many years.

I am 55 and lived my entire life in Texas and one of the few white guys not getting skin cancer cut off my head or face. I attribute this to wearing hats a lot off and on in my life. My brother never wore hats and my dad stopped after LBJ left the office. Both had skin cancers removed, it is pretty common for white guys down here, but I escaped it thanks to hats. BTW, JFK not wearing a hat at his inauguration is the reason American men tend not wear hats any more. People tease me about my long beard making me look Amish with the hat, but no one gives me a hard time about the hat, and women tend to love it. I have a Churchill Homburg, a navy Stetson Fedora, a gray Stetson Open Road, a nice Resistol cowboy hat, and a beat up Resistol cowboy hat with a rattlesnake band that I skinned myself for yard work and such. It keeps the sun off my face in the summer and my head warm in the winter. If you want to wear a hat, wear one. Just get one that fits, like the video says. The biggest key to wearing a hat is to make it fit your outfit. If you wear a nice hat like a fedora, open road, or homburg, then you have to be wearing nice clothes. If you wear a beat up hat, don't be wearing a suit.

The euphoria is 2real4me

I wish the fedora could come back in style like it was in the 40's and 50's

Hat is too small for your head...

The pics of celebs wearing hats either in a movie scene or actually in public were awesome. They made me laugh at times. Well done!

I wear a Trilby style Fedora with a little bit oversized suit coat and I love it. I find it awful that men don't find this classy anymore, my father thinks that I look like a mobster and I don't really like that term. I love the older styles more than the modern looks of today. I'm still in my teens and every time I wear a cabby or a Fedora I'm told that I look like an old man. I am confident about what I wear so it doesn't bother me that much. To me, that just means that I dress more mature than I'm expected to wear.

More on hats! We need to bring this back

One of the nice things about being a middle age man is you pretty much can wear what ever you want. I love hats from the Stetson Cattleman, to the newsboy, to the bowler. People just dressed better in the late 1800s to 1930s.

About four years ago I started wearing a Fedora.  Now I own seven of them.  I am 6'5" and 225 lbs.  I been told I wear them well.  As I get compliments from the ladies.  At bars I been told that I look like a musician.  I may look the part, but unfortunately I not one.  Thank you for posting this video!  I have really enjoyed all your videos.

I've been wearing fedoras with my suits for work in the winter time for 5 years now. Winter hats mess up my hair but these keep my head warm, if not my ears. Now everybody wears them. I use pomade instead of gel to keep my hair under control. Looking forward to the series!

Personally I prefer and wear flat hats at work with casual attire. I appreciate the work and research you have put into your articles & videos.

I've built a large collection of fedoras--not trilbies, the brims are 2 inches or more. And yes, I'm usually the only one wearing them, but sometimes I've seen older men wearing them too. I'd love to see you talk more about hats again.