The Private Man

Attraction and dating information for all men


There was a time when a man was expected to have a matching hat – usually a fedora – for each suit. The hats were custom-made and required regular maintainance at the local haberdashery. According to the men of the time, the hat was often considered a nuisance because they were expensive and when the wind was blowing, required one hand to hold on to the expensive accessory. So, like spats and cravats, the hat fell out of favor with men. The baseball-style cap I simply discount as they are so ubiquitous and so plebian.

Three weeks ago I was at the local church’s annual rummage sale. There, I picked up some things for my swingin’ bachelor pad. I also bought two hats. I’ve never been much of a hat guy because my head is, well, huge. Finding headgear that fits has always been a challenge for me. Buying a motorcycle helmet is an epic struggle. Normally, a double extra-large fits my noggin but sometimes that is even too small. So when I find a hat that fits, it’s quite unusual. At the rummage sale, I actually found two hats that fit. At only a dollar a hat, I bought them both.

One hat is more of a hipster-type thing. It’s got a modest brim all the way around with a fedora-type crown. It’s brown and made of tightly woven flat straw. The band is red and blue with a “Red Guitar” plastic icon on the band. It somewhat resembles this:

This hat I wear in the evenings after sundown. It’s not formal headgear like a homberg or a bowler. Yet it’s perfectly sufficient for a stylish statement to set me apart from all the dudes wearing those awful baseball-style caps.

The other is a Panama hat. It’s tan and with a wide brim, perfect for the hot Florida sun. It looks quite a lot like this:

This is my daytime hat (not at work, obviously) when I walk into the village, Lucy my dog on her leash. With some cool sunglasses, a nice shirt and jeans, I cut a fine sartorial figure when compared to the usually very casual (re: slovenly) dress that is the norm in these parts.

Since I’ve started wearing these hats, I’ve noted that people treat me differently. Perhaps my willingness to stand out gives me more confidence and people are responding to that. Perhaps it’s the actual hat and the fact that it’s unusual for a man to sport one. At a recent party, my hat was quite the hit and the topic of conversation and even a bit of envy from the guys.

Just this past evening, I was out walking Lucy and ran into three female friends, two of them I have not seen in a while. With the dog, the hat, and my mood, the indicators of interest where quite high. It was remarkable.

I think for my next hat, I’ll buy a fine red Fez with an elegant gold tassel. No, I’m not getting a huge, furry hat.

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20 thoughts on “Hats

    • Well shit, I remember that post and perhaps I should have just linked to you! Given the hot and sticky weather down here, the headgear must allow for maximum airflow lest sweat stains ruin the hat’s material and then look unsightly.

      While I really don’t like the term “peacocking”, when a man stands out from the crowd with his fashion sense it’s a statement of his confidence.

  1. I have five fedoras-two black, one navy blue, one gray, and one brown. Each matches a different suit. I consistently get compliments from women and men. I’ve probably gotten more compliments on my hats than any other piece of clothing I own.

  2. Dirt Man on said:

    I like a good hat now and again. I still wear baseball hats, but not in a tilted to the side, obnoxious way. I get a similar difference in how people treat me when I wear a tie. It’s funny how people respond to clothing. Like they say, the suit makes the man.

  3. AnonymousDog on said:

    I seldom go outside bareheaded, except in the mildest weather. I don’t think it was the nuisance factor that drove hats out of style so much as ‘bigger’ hairstyles on men. Once hats went generally out of style and became uncool ‘old man’s wear’, retailers became unwilling to devote space and other resources to an inventory of multiple styles of hats in multiple sizes. Except for a few retailers who specialize in hats, you seldom see more than one hat style available at a men’s wear retail store, and that style will be aimed at the younger ‘hip’ guys who are willing to buy hats as a fashion accessory, not as practical, everyday head gear.

    Most modern day vehicles, excepting pickups, force you to take your hat off while driving. Baseball style caps are a much better fit in cars. Also, few public accommodations provide secure places to put your hat when you’ve taken it off inside. Here in the Midwest, I see guys (in overcoats and gloves!)going bareheaded on the coldest days of the year, or wearing stocking caps that can be shove into a coat pocket when taken off.

    Personally, I avoid ‘fedoras’ as being a bit too uptown for a country guy like me, preferring the more conservative styles of ‘Western’ hats for formal occasions, and baseball style caps for casual wear. I plan on buying a new straw hat every summer as sweat stains get more noticeable after they have set in the closet all winter. My older, stained, felt and straw hats get worn doing outside chores or recreational activities.

    I have noticed that wearing a hat tends to get one of two reactions, a favorable one, or, an unfavorable one evidently stemming from some folk’s dislike of non-conformity. Wearing a hat does make some kind of statement, and some folk’s evidently don’t want a guy to make any statement, hat-wise.

  4. Years ago, I considered wearing a fedora mainly as a fashion accessory when I’m in a more “dressy” mood. Trouble is, as you mentioned, where do I put the hat when indoors? Also, as I grew up in the northern Midwest, where there are four seasons with cold winters, wearing a fedora or other hat that didn’t cover my ears was infeasible. I’ve worn some kind of stocking cap since I was a little boy and continue this because it keeps my head (and ears) warm.

    I remember when I started my freshman year in college, over 20 years ago, having a professor who wore an overcoat and a fedora, along with a neatly trimmed mustache and horn-rimmed glasses. He pulled it off quite well and made him look more distinguished, despite being on the young side of 40 and not in possession of much gray hair. I always thought, “I hope to be able to pull off his look someday when I’m older and more established.”

  5. sestamibi on said:

    Here in rural northern Nevada, I often sport a cowboy look (even though I grew up in NYC), complete with grey felt hat, boots, and big buckle belt.

    I have gotten numerous comments about how cool the hat is (some of them on the street in NY and NJ when I go back to visit), not to mention cash offers for it!

  6. The key is to wear the hat, not let the hat wear you.. Ie, if you are under 5’8 do not wear a cowboy hat (10 gallon hat). I am a shorter man, so I wear a black fedora, or a hat with a smaller brim. Being stocky, (short and fat) I am looking for a derby!

  7. “It’s a fez. I wear a fez now. Fezzes are cool!” đŸ˜‰ yes, I am an uber geek.

  8. Senior Manchild on said:

    I had to look up spats and cravats( I vaguely knew what a spat was). A cravat makes for a distinguished appearance but thankfully that silly spat has gone the way of the dinosaurs.

  9. on said:

    Finding a good panama hat is hard, any suggestions that don’t break the bank?

  10. Fuckaire on said:

    What if you’re bald and your head is dead sexy???

  11. Candide on said:

    I’ve got a quite decent collection of hats, mostly fedoras, and always get looks and compliments from people.

  12. John G on said:

    You had mentioned you had a large head. Getting a fez for a big head is kinda a chore. I got one and a big head like you and it barely works. If it’s too small, you look really incongruous.

  13. My father was known for years as “the man in the hat”. He was already fairly tall, but the hat added a good 3″ to his apparent height. Plus he stood out in a crowd. Contractors could see him coming from across a field because of his distinctive hat.

    But it has another advantage too, as he showed me. His reputation as “the man in the hat” was so secure that when he took it off he virtually disappeared from notice. He proved it to me at a funeral of an acquaintance once, crossing the room once with a hat and once without. With the hat he was stopped seven times by friends along the way. Without the hat he wasn’t stopped once. It made an impression.

    As to what to do with a hat indoors, many men have a hard time figuring out what to do with their hands. Use one problem to solve another. Just make sure to handle it by the brim, though. Handling it by the crown crushes it.

  14. Matt on said:

    Ian, did he wear a stetson? aka “cowboy hat)? your father that is.

    also an aside, my theory is that the taller the man, the wider the brim and vice versa..

  15. Bill Powell on said:

    I’m definitely a hat person. Fedoras, cowboy hats, straw panamas from Panama, I’ve got the gamut and wear them pretty regularly, and I still have a full head of hair. A man who wears a proper hat stands out, and I can say that I got my current girl because I wore a pure wool black fedora the first time we went out. My best hat however, is a 1901 New York bowler that I found purely by accident at a street festival in a small Florida island town. It was in perfect condition, had the original hat box and the guy only wanted a Benjamin for it. I got it home, went online to check out what it might be worth and like I suspected, it’s worth about a grand. That’s now my go to hat when I’m suited up, and it gets me all kinds of attention. Especially when I tell the story of how old it is and where it was hand made.

  16. Love the panama hat. Find yourself a matching white suit and you’ll look like Guy Caballero from SCTV.

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