Chip Shots: Hats Off Works Best For Me

May 11, 2024 at 8:00 a.m.


My only interest in The Kentucky Derby (took place last Saturday) is to see some shots in the audience to see how many people have wealth but lack good taste. As departed comedian Joan Rivers once said, “Every woman needs a gay friend… to tell her no!”
Trust me when I tell you many in attendance probably don’t have gay friends, nor was it likely they know any gay people at all. When a straight, middle class, middle-aged man from the fashion wasteland that is the Midwest can tell something looks bad (especially the hats), this proves wealth and taste are mutually exclusive traits.
I’m utilitarian when it comes to hats.
I rarely wore a hat when I played in adult and Air Force slow pitch leagues unless I was going to be at a tournament where my scalp would likely burn. I won’t even start with my Little League look.
Hats in the 1980s look similar to hats coming back in style among younger age groups: the nylon mesh backing with the very rigid, flat bill. I look like a cartoon character when I wear them.
There is a Tiger football hat given to me, however, with a hard bill without being too wide, and its skull part is not roomy enough to hide Ratatouille. It’s a nice hat with a precise fit, it represents – specifically - my favorite high school sports team, and it’s one of the few hats I feel comfortable wearing in public in terms of a complementary look and a proper fit.
Most of my hats have the fabric close to the skull with a bill I can shape into a convex bend. If you see me in one of those, I meant to do that.
I also wear an unflattering bucket hat because its material wicks the sweat when I’m in the yard, or out on the water. Its tie strings are handy to keep it flying from boats I board occasionally whose pilots like to get the speed up to 45-50 miles per hour.
If I’m wearing my black bucket hat, I’m not remotely worried about having good taste. It’s 100-percent utilitarian.
If I were to wear a hat to make a fashion statement, I have no idea what I would wear. I’m glad I’m not a woman who has plans to be at the Kentucky Derby, nor at a Derby party in her hometown. I have enough challenges with headgear.
I could care less about attending this race anyway, nor watching the race on TV. I just want to see the train wreck comprised of wealthy people (who have vulgar wealth in some cases) showcasing their unbelievably bad taste.
I had a phase in 2004 and 2005 where I intentionally wore hats that weren’t just ball caps or bucket hats, but even as stylish as they were on the rack, the flat backside of my head made the studied look I attempted dead on arrival.
The look was broader in its brim and lower in hat height than a fedora, but less expeditionary looking than Indiana Jones’ look. I had one in brown and in black.
Hey.
Will you please stop laughing at me?
I learned my lesson over 19 years ago.
Thank Heaven I was not an accountant in the 1960s, the chortles and snort laughs I would likely get in the elevator each morning and evening.
I struggle in these times, too, when it comes to fashion of any kind. I’m like an insightful movie critic who can’t act nor direct. I have little trouble spotting bad taste, nonetheless. I’m not sure what’s in the secret sauce, though.
A smart aleck friend of mine once texted me, “My wife and I were Facebook stalking you to see if there was a time in your life you didn’t dress like Larry David, especially those droopy pants. Do you own jeans?”
To my credit, I don’t wear sport jackets with my get-up as often as Larry David does.
While I sometimes wish I were born as early as 1957, I’m glad I was born in 1964, completely missing the men’s dress hat era.

My only interest in The Kentucky Derby (took place last Saturday) is to see some shots in the audience to see how many people have wealth but lack good taste. As departed comedian Joan Rivers once said, “Every woman needs a gay friend… to tell her no!”
Trust me when I tell you many in attendance probably don’t have gay friends, nor was it likely they know any gay people at all. When a straight, middle class, middle-aged man from the fashion wasteland that is the Midwest can tell something looks bad (especially the hats), this proves wealth and taste are mutually exclusive traits.
I’m utilitarian when it comes to hats.
I rarely wore a hat when I played in adult and Air Force slow pitch leagues unless I was going to be at a tournament where my scalp would likely burn. I won’t even start with my Little League look.
Hats in the 1980s look similar to hats coming back in style among younger age groups: the nylon mesh backing with the very rigid, flat bill. I look like a cartoon character when I wear them.
There is a Tiger football hat given to me, however, with a hard bill without being too wide, and its skull part is not roomy enough to hide Ratatouille. It’s a nice hat with a precise fit, it represents – specifically - my favorite high school sports team, and it’s one of the few hats I feel comfortable wearing in public in terms of a complementary look and a proper fit.
Most of my hats have the fabric close to the skull with a bill I can shape into a convex bend. If you see me in one of those, I meant to do that.
I also wear an unflattering bucket hat because its material wicks the sweat when I’m in the yard, or out on the water. Its tie strings are handy to keep it flying from boats I board occasionally whose pilots like to get the speed up to 45-50 miles per hour.
If I’m wearing my black bucket hat, I’m not remotely worried about having good taste. It’s 100-percent utilitarian.
If I were to wear a hat to make a fashion statement, I have no idea what I would wear. I’m glad I’m not a woman who has plans to be at the Kentucky Derby, nor at a Derby party in her hometown. I have enough challenges with headgear.
I could care less about attending this race anyway, nor watching the race on TV. I just want to see the train wreck comprised of wealthy people (who have vulgar wealth in some cases) showcasing their unbelievably bad taste.
I had a phase in 2004 and 2005 where I intentionally wore hats that weren’t just ball caps or bucket hats, but even as stylish as they were on the rack, the flat backside of my head made the studied look I attempted dead on arrival.
The look was broader in its brim and lower in hat height than a fedora, but less expeditionary looking than Indiana Jones’ look. I had one in brown and in black.
Hey.
Will you please stop laughing at me?
I learned my lesson over 19 years ago.
Thank Heaven I was not an accountant in the 1960s, the chortles and snort laughs I would likely get in the elevator each morning and evening.
I struggle in these times, too, when it comes to fashion of any kind. I’m like an insightful movie critic who can’t act nor direct. I have little trouble spotting bad taste, nonetheless. I’m not sure what’s in the secret sauce, though.
A smart aleck friend of mine once texted me, “My wife and I were Facebook stalking you to see if there was a time in your life you didn’t dress like Larry David, especially those droopy pants. Do you own jeans?”
To my credit, I don’t wear sport jackets with my get-up as often as Larry David does.
While I sometimes wish I were born as early as 1957, I’m glad I was born in 1964, completely missing the men’s dress hat era.

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