I am a a fan of hats be they Panama, flat, bush or baseball. I tend to default to baseball alternating between a tidy Garmin team cap or a sky one. I had the sudden realisation that as I am aproaching 40 that I may look a prat in a hat.

When you GAS about what other people think 😉

I’m 50 and I have one hat, a baseball cap in orange with ‘NY’ on the peak. I wear it when I need to keep the sun out of my eyes and sunglasses alone can’t do the job. I don’t care what other people think it looks like

Turned 40 last month, still rocking a skip.

I’d go with your instinct on this one.

I wear my New Jersey Devils BBC with pride, at 58. (even though I prefer to follow Calgary Flames)

39 and still wear one but I hate the new flat peak designs, can’t seem to get the proper ones.
I do have an issue with a massive head, my current favourite had to be imported from Sweden as I couldn’t find any other XXL Flexifit hats (It’s a Fox Racing one).

I hate the flat skip too.

I love the ones with gold sticker on, I giggle every time I see one and the weapon who’s wearing it.

I think about 18momths after you stop being an American.

When you were born.

Baseball caps look ridiculous on anyone, but that’s just my opinion – if you like it, then wear it.

I quite like hats of various types – if I wear a peak, it will be a military style cap though.

Wear what you want, just don’t expect everyone/anyone to think it’s cool apart from you. As long as you are comfortable in it, then sod anyone else.

Puberty.

I do have an issue with a massive head, my current favourite had to be imported from Sweden as I couldn’t find any other XXL Flexifit hats (It’s a Fox Racing one).

There’s a reason for that- you’re 39!!!!

Sealskins waterproof baseball cap is the greatest garment ever developed, I want to be buried in mine

When you were born.

Agreed. Hideous things.

You’re your own person: Do what you want.

Think it depends on your look. I also wear nhl & mba caps, plus beanies, and think I will when/if I get old. A 40yo twit in a cap with a flat peak with a sticker on would make me cringe. But same goes for a 20yo 😉

Backwards? Front-wards? To the side?
This makes all the difference.
APF

To wear a trucker cap you need to be a trucker, be a bit greasy & called Billy-bob

All other hats are ace though, my boss rocks a Brown Derby

42 here. Usually wear a cap.

Got one on as we speak.

Because I’ve just got up, had to nip to the garage to get some bagels for breakfast, had ridiculous bed hair, can’t be bothered to wash or restyle it in any way until after my ride, which will be the next time I’ll wear it (there and back, same reason becoming helmet hair after)

Also useful as a glasses wearer to keep drizzle at bay. Or sun out of my eyes (or, as I have a nose that is exactly the same angle as our latitude and hence the sun hits it at 90 degrees and so can burn it in seconds flat, keeping it off that)

You can still get sports style caps in sports direct. I agree the flat peak / sticker ones are an abomination. My daughter has one that I steal and wear sometimes for the purpose of looking like a **** and embarrassing her. It’s a Dad thing.

I’m 47 and wear a cap every day at work, shame its a bump cap and says Severn Trent on the front !!
Failure to wear it ends in a warning 🙂

12.

Unless you’re a chav.

Unless you play a sport/work safety/F1 driver.

There are different shapes of baseball cap and they suit different faces and heads. I have a couple, which I use for sun protection and I happen to think are quite OK looking. I have 27 other types of headgear as well…

I wear my Pittsburgh Steelers cap sporadically, as a very casual piece of atire it’s just fine. And handy in the summer heat.

52 and still wearing my Bentley Boys one from Le Mans 🙂
also have tweed flat cap and a huge dose of dgaf … I’m comfortable !

OP where they come from people of all ages wear them. I didnt realise there was a limit?

I may look a prat in a hat

As William Hague famously proved ?

When you get too old to care about sunburn and heatstroke! I know I look like an idiot in one, but I also know I act like an idiot when I have too much sun and get grumpy!! More practical than other hats for active outdoors use in summer I reckon. Not sure I’d wear one in February though

‘Too old to’

Who says this? People who are paranoid?

Some people never look good in certain headwear. Its usually if you have a weak jawline/chin.

Garmin team cap? Are you in the team?

Wow, some great ‘judgemental’ comments above, I shall add my own my suggesting anyone who wears a flat cap & doesn’t have a whippet or ferrets & come from Yorkshire looks really silly (peaky blinders seems to have brought them out in droves). Was recently temped to buy a tweed baseball cap (haven’t worn a cap in 20 years but do love my canvas bush hat) but too close to the classic Burberry for comfort. Do/wear what you want & let the haters hate, WGAF really?

Sealskins waterproof baseball cap is the greatest garment ever developed, I want to be buried in mine

They do what? Cool! [Scammers off to find a picture of one]

Ohhhh tempting!

Make sure you wear it like this – and post a pic. Oh and stitch the waistband of your jeans to the bottom of your boxers 😉

Garmin team cap? Are you in the team?

Garmin have a baseball team?

I don’t think age should be the qualifier for baseball-hat wearing, rather, self-respect 😉

At times like this, you need to defer to an authority on such matters. Love him or hate him, the much maligned (unfairly in my view) Pete Docherty, knows a thing or two about hats. And as he correctly observed in A Time for Heroes:

“There are fewer more distressing sights
Than that
Of an Englishman in a baseball cap”

[video]https://m.youtube.com/watch?v=HAusT_Yl1gE[/video]

My 66 yo dad wears a baseball cap on sunny days when he does the gardening or walks the dog. He still looks 66 in it but not particularly daft imo. Although his is the sort you would find in marksies or cotton traders, so not sure how a wide flat brimmed one with a shiny sticker on it would look on him!

At the cusp of 40 you’re the wrong age for a baseball cap.

You’re just too old to get away with it “looking cool”, and just too young to not GAF that you can’t. You’ll be wearing it with pride again in a year or two.

Driving, sunlight and drizzle: I’m now too old to GAS preferring comfort. But, as a gentleman, one removes one’s hat on entering a building.

I gave up wearing baseball caps several years ago when cloth caps started to get more popular in different styles. I don’t like the traditional flat ‘at, or what’s known as paperboy caps, but I found duckbill caps, which have the benefits of the baseball cap, having a decent bill to keep rain off my glasses, and sun out of my eyes, and stop the top of my head getting sunburned!
I’ve got a couple a bit like this one, one’s a Stetson!

Really comfy, and I don’t look a tit wearing them.

^^^ 😆

about age 14 is the correct answer to the question posed by the OP