Hat season is back for those of us in the Northern Hemisphere. Before long it’ll be the dead of summer. And even if you hate wearing a hat, spending all day outside in the sun without one is inadvisable. Especially if you’re fair skinned. Like all “rules,” these aren’t unbreakable. They’re more suggestions and guidelines. Except for #14.
Above Photo Credit – Ed Yourdon
1. Half the battle is being confident that you look great in a hat.
2. If you’re not, you won’t.
3. For every year above the age of 35, you’ll look exponentially better in hats.
4. For every hat size above 7 1/2, you’ll look exponentially worse in hats.
5. If your head is big, those dual size L/XL hats won’t fit
6. The easiest hat to wear is still the ballcap. Ultra casual only. Consider the Cooperstown collection “Franchise”.
7. If you have no sports affiliation, logos can sometimes work. Just keep it subtle.
8. Trilby = easier to wear than the shorter, flatter pork pie.
9. This Original Penguin option is more or less on the right track. Maybe.
10. But then there’s also the The Classic Panama
11. Driving caps look good on approximately 8% of the population
12. Floppy Bucket Hats – No.
13. Straw Cowboy Hats – No. Unless you know how to drive a tractor or your name is Kenny Chesney.
14. Hats with Ears – Quintuple no. The hell is wrong with people.
15. Well proportioned straw hats with a chambray band – Sure
16. You wear the hat. It does not sit perched on your head like a parakeet.
17. A white hat can work, but if you’re wearing more white than that, be ready to give tours of Jurassic Park
18. If your hat says “Cocks” or “Morehead
19. Y’know they do make scalp sunscreen
20. When in doubt, don’t.
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sorry Joe, but -1 for recommending the ball cap…recommending to gear up like your little league coach? Save the cap for the stadium.
how about a round up of some of your picks
The first 2 rules are spot on, the rest are shit. Do yourself a favor and look up a real hat store or a hatter, give them a call and ask their advice, better yet give them a visit. Salmagundi Boston is an excellent start.
I am going to have to disagree with the driving cap comment. I love driving caps and see alot of people in the Boston area that wear them. I do think younger people wear them better becasue now of the level of cool it has..i receive plenty of compliments on it…I keep getting told I look like Ne-yo since i always wear a fedora or a driving cap. With a very well groomed low cut caesar.
DC loves some hats. Something about that old-school CIA vibe makes people break out the fedoras and the long trench coats.
Rule number 3 is critical. If you don’t have lines on your face, chances are you can’t pull off any hat that’s not a ballcap. The older you are, the more that fedora makes it look like you’re a Cold Warrior spook that speaks 20 languages (one of which is violence).
I’ve seen a lot of college-age kids try to pull off the fedora/trench coat look. It’s rough.
I agree with Joe… driving caps make the majority of folks, even those who think they’re cool, look like schoolboys from 1920.
seems to me location has a lot to do with it. I live in Florida, and here its pretty easy to pull off a straw trilby or narrow-brimmed fedora in the summer, but you couldn’t wear a driving cap here with out getting the “Is he serious?” looks.
New England seems like a good place to wear a driving cap, and places like Texas you can’t really get away with either
I kind of like the 1920’s school/page boy look on some people (myself included).
Sorry Joe, but I gotta call BS on this too. Granted, at 38 I’m probably a good bit older than your usual reader but a good hat has its place. I wear a hat every day. Depending on what I’m wearing that day (suit, business casual, jeans, or shorts & shirt on the weekend), I’ll vary my hat from a fedora to a driving cap & most everything in between. Granted, I don’t wear my derby but about once a year, but you get the idea.
I live in Alabama so my felt fedoras have already been put away for the summer. I’m now wearing cotton pub caps/duckbill caps, straw & cotton trilbys and narrow-brimmed fedoras. I do have a straw porkpie that I wear on a more casual day with jeans & an untucked shirt, but I do agree that it doesn’t look right with everything.
I do agree about the big headed guys not being able to wear the dual sized hats. I’m a 7 5/8 and I gave up a long time ago on trying to ever find a hat at a non-hat store. Yeah, stores like Target have some “hip” looking hats but only if you don’t have a big head and you’re still in high school. If you truly want to wear hats and look good in them, buy quality hats. Go to a haberdashery and get fitted properly. Also know that not every hat will fit you just right, even if it’s your size. It helps to wear they type of outfit you want to buy the hat for when you go so you can get the entire “picture” while you’re shopping.
As for Mike’s comment about driving caps looking like schoolboys from the ’20s, be sure you’re not confusing a driving cap with a newsboy. A lot of people will use the term driving cap to lump several different caps into one category when in reality, they are all quite different.
The main issue I have with guys trying to wear hats, isn’t how they look in them, but the etiquette that they lack in wearing them. There’s an entire list of do’s & don’ts when it comes to wearing a hat, but my biggest pet peeve is when a guy is wearing one while eating. Have some respect for your table mates & remove your lid. There are others, but I’ll not get preachy here.
I agree with poolboss on the baseball cap. Leave it for the stadium. And please…never…ever…ever… wear it crooked like someone just slapped the piss out of you. Keep it straight with the bill in front. Unless you’re hoping for a 9th inning rally, then by all means turn it upside down & backwards (or whatever helps get that winning run across the plate).
I’m not saying wear it with a blazer. But jeans and a t-shirt? Or a polo and shorts? Why not? I wear ball caps on days when I’m casual, outdoors, and it’s friggin’ searing hot. Lemme quote Eddy Teach a few comments down: “Rule number 3 is critical. If you don’t have lines on your face, chances are you can’t pull off any hat that’s not a ballcap.” It’s not easy man.
“I do have a straw porkpie that I wear on a more casual day with jeans & an untucked shirt” Feel free to call B.S., but my friend, you’re in the minority. I have no doubt you can pull it off, but you’re in maybe 1% of the population. And as far as keeping the ballcap straight? Well… yes, of course.
Waitaminute… so if the rest are shit, you’re all about Floppy Bucket Hats and Straw Cowboy hats? I think you’re a big time hat fan who didn’t read all of em’. Like I said. Suggestions and guidelines. Not rules.
When all else fails have a female (wife, girlfriend, sister, friend etc) come with you when looking at hats, or any clothing really, and listen to them when they tell you if things look good/bad on you. My wife loves me in hats, so I picked up a couple of decent pub/duckbill caps and a fedora.
I agree for the most part, but is there any hope for those of us who have a hat size around 7 3/4?
And a word to the hipsters. Look up proper hat etiquette. Take off your damn hats in restaurants, especially those stupid ball caps.
You will note that he recommended the Cooperstown Collection which are the classic hats that have a classic look. Remember how awesome old ball players looked? That said, avoid the 1970s Pirates and Astros.
True words. Hat etiquette is a dying art.
True words. Hat etiquette is a dying art.
My head is enormous (size 8) so hats are just a sad fantasy for me but I agree with others. Learn basic hat etiquette and stop thinking you can wear a hat anywhere at all times. Baseball caps are very, very casual. Stop wearing them to anything but the park (ballpark or otherwise)
While we are on the subject of ballcaps, let me just rant about how much I hate the current fashion that kids have of wearing caps. Slightly oversized boxy caps with flat bills with the STICKERS still on the bill. I’m seeing guys in their 20’s wear their caps like this as well. If you wear a cap all the time, hey, lord bless you, but at least take the frickin’ sticker off!
Though his suits (still) never seem to fit him properly, the Prez looked kinda cool when he was the Prez-elect donning the White Sox hat with his shades & suit.
I’m pretty sure jwm is wearing a straw cowboy hat on top of the floppy bucket hat he’s already wearing.
I agree; I went to a restaurant for happy hour yesterday and I was wearing a cap because I didn’t fix my hair…and because, well, GO SHARKS! However, I still took it off because I’m not a jackass, and because I have some class and decency.
I think they’re going with the “I just stole this” look
As a young person with a giant head, I suppose hats are a no-go for me.
right on Matt
PREACH on my sartortial brother PREACH…
God, I really hope I’m in that 8% because I wear driving caps a good 90% of the time.
IMO, they are the easiest casual hat to pull off without looking too dressed down (as with a baseball cap) or trying too hard (as with a fedora/trilby/porkpie/stetson).
Thanks Maxman
I dont know, I always thought (on the right frame) the driving cap make people look like a Pulp novel villian or thug. Now I personally wear a driving cap regularly but I’ve liked them since before they became “stylish” or “trendy.” I really hate how when something catches on you get lumped into the rest of the hipsters even though you truly like the style of a hat.
Whatever. I loved this post. Thank you for it.
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