Hats: Help, please.

Please note before anything: This is silly, and I know it. I'm hoping it's fun.

Due to a combination of family history and some stuff the dermatologist will be looking at shortly, it seems I should up my diligence on wearing hats when I'm out in the sun.

The thing is... I don't like most hats that much. I mean, I do like them in concept, but I find most of them to either be horrible by association, too affected, incompatible with my usual jeans-and-T-shirt, or by this time I'm just in a snit and everything is terrible. What I'm hoping for is that someone can introduce me to types of hats I'm just failing to think of. Or maybe change my perspective on some hats. Or just mock me 'til I get over most of the objections I have below...

It could also be argued that I'm having a quasi-age-related sartorial crisis of a sort. It's slow-burning. But perhaps if I managed to get back to doing better than jeans and T-shirt, some other hats would feel more reasonable.

I can wear a baseball cap, kinda, I guess. It's... not really my thing. I have a plain black one and a Summit one. I think the last time I wore either was attending an extended-family little league ball game several years ago. Maybe if I can find the right one that's a bit more classic-looking than most of what's around now?

I wear cycling caps sometimes, and they are geeky as hell and just don't work with some clothes/venues. It's hard not for it to feel like an affectation despite having been attached to bicycles and bike shops for the better part of forty years. I find them the easiest to deal with for yardwork and dump runs and so forth. I only wear them on the bike when the weather's crap.

I have a tweed pub cap kinda thing, and that's dandy for spring/fall cool temps and appropriate venues, but doesn't work everywhere.

Stocking caps are great, but I wear those to keep out the cold, not the sun.

I have a straw hat not unlike this, but it only works if I'm dressed a bit better. Not necessarily dressed up, but it feels wrong with a T-shirt. It makes me want a linen suit, and how often can I wear that? (I need a '27 Aston Martin to autocross...):

And I have a bowler, but that's just a novelty. I got it when I went as Magritte's "The Son of Man" painting for Halloween, and unless and until I get an old British saloon of some kind, it doesn't make much sense.

While it prevents me ever being a Boss-Level Autocross Dude, I cannot do the sombrero-size sun hat of any type. It's not on. I do respect those who can pull it off.

What am I missing?

I was in the same boat. I bought a wide brimmed Tilley and now I have known some people (for years) who have not ever seen me without it. Machine washable and warranty replacement when I wear it out. I bought one almost 20 years ago, have paid shipping for two replacements, and paid $5 for a model upgrade along the way.

They mostly have narrow brims for boating, but I went wide for better sun protection.

Edit for similar pic. My first was like Toyman!'s pic, but I upgraded to one similar to this. Expensive? Sort of. 20 years ago I spent $60 on a hat. Postal service two ways, two times, and $5 for an upgrade is not a lot considering I wear it every time I go outside, and it still looks good enough that many people think I keep buying new ones, but I just keep washing this one.

Tilley is my preferred sun hat. Durable, lightweight. Not very cheap though. Around the shop I wear a ball cap. 

I go with various hats from Outdoor Research depending on sun or rain.

Sun:  https://www.outdoorresearch.com/us/mens-sun-hats

Rain: https://www.outdoorresearch.com/us/mens-rain-hats

Brazillian tarp hat as seen in Zombieland.   Durable, and comfortable.  I bought one years ago and its been my go to hat.  Rinse it off with a hose after sweating in it all day and throw it out on the patio to dry.   Wife hates it, she actually bought me a "nice" hat to replace it.  I still wear it when working around the farm and call the other one my "goin to town" hat.

If I'm just trying to keep my ears from getting sunburnt, a cheap fisherman's hat does the trick.

For better protection, I have a Minnetonka folding hat that I really like.

When I want something lighter weight, but still with a decent sized brim, I have a tarp hat.  

Go big or go home

I just bought a Tilley (Canadian living in Aus).  Not cheap, but I expect it will be one the last hats I buy.

Came here to recommend Tilley. One day I'll own one. 

JThw8 said:

Brazillian tarp hat as seen in Zombieland.   Durable, and comfortable.  I bought one years ago and its been my go to hat.  Rinse it off with a hose after sweating in it all day and throw it out on the patio to dry.   Wife hates it, she actually bought me a "nice" hat to replace it.  I still wear it when working around the farm and call the other one my "goin to town" hat.

 

Have one as my 'out in the sun' hat as well, and I love it.  Takes all the abuses of the day without worry.

Eddie Bauer for me. I had one I wore at every lemons race, every hike from New Zealand to the Grand Canyon and it lasted me for 10 years. I replaced it with the same. 
 

for me the draw string is essential as it keeps it on my head in the wind. Regardless of the brand, these hats work. After a long hot day in the sun you'll feel better having worn it than without. 

This is relevant to my interests as I need to find a new Autox Hat.  I'm hoping to fake talent as the most qualified usually have the largest hat.

84FSP said:

This is relevant to my interests as I need to find a new Autox Hat.  I'm hoping to fake talent as the most qualified usually have the largest hat.

Here you go:

Seriously though, the Minnetonka is great, in that it folds up when you don't need it, and it is heavy enough that most wind doesn't blow it off my head.  The tarp hat is nice, too, especially when you want something lighter weight, but I had to add a boot lace to it as a hat strap to keep it from blowing away in high winds.

jgrewe said:

I go with various hats from Outdoor Research depending on sun or rain.

Sun:  https://www.outdoorresearch.com/us/mens-sun-hats

Rain: https://www.outdoorresearch.com/us/mens-rain-hats

 

I've been very pleased with my OR Seattle Sombrero.  If their sun hats are as good, they would be fine.

Nathan JansenvanDoorn said:

I just bought a Tilley (Canadian living in Aus).  Not cheap, but I expect it will be one the last hats I buy.

I have a Tilley that I inherited from my father in law. It must be 40 years old & still serves well.

As anybody who's seen me at an event can attest: Tilley. It's not the epitome of style, but it works well enough with almost anything and it keeps the skin cancer away.

Pro tip: buy it in person if possible, as there are a bunch of different sizes. 

You're looking at this all wrong. You had it right in your post and didn't even realize it, just buy more linen suits. Invest in some aviator sunglasses and a subtle watch. You'll be cool, comfortable, and covered; the trifecta.

I regularly wear an all-leather Henschel safari hat. Unfortunately, it looks like they're discontinuing that model. Not fancy, but classier than a ballcap. Crushable. Great in rain or shine.

Henschel is a good choice to looks at for a variety of styles that are everyday wear.

I'm also fond of a classic flat cap / driving cap. Classier than a ballcap and just as convenient. Actually, more convenient, since I can generally fold it over around the brim and stuff it in a jacket or back pocket.

I think the key is to get one in a solid and understated cotton. Not plaid tweed that makes you look old. (If I ever own a Caterham though, I will drive around in a tweed flat cap, leather driving goggles, fingerless gloves, and waist coat.)

I have one in this style, in a nice gray:

In reply to Error404 :

The problem with your suggestion is finding a good linen suit. They're scarce as hens' teeth around here.

I have no recommendations but all the love for Tilley reminds me 20 odd years ago I had dealings with dealings with the Tilley family, my family’s interests not theirs. They sold out and Tilley is owned by a private investment co. Andy product is made in China.

Tough one. I used to kayak a lot and I used ones like Dculberson - but any hat with a saggy brim looks slovenly to me. Don't like ballcaps, but am kinda ok with foreign legion ones:

The problem with good-looking stiff brim hats like Stetsons and such is that you have to be careful with them. I might have to try the Brazilian tarp hat. Sounds like it will take the abuse I deal out.

Kreb (Forum Supporter) said:

The problem with good-looking stiff brim hats like Stetsons and such is that you have to be careful with them. I might have to try the Brazilian tarp hat. Sounds like it will take the abuse I deal out.

It will.  I am not kind to mine, had it about 14 years now.  As a bald man all my sweat goes right into the hat so it gets gross, hose it off, throw it out to dry and keep rocking.  Its been indestructible.  

I'll wear anything with a wide brim or other real shielding. Baseball, flat, cycling, etc don't cut it.

Cancer sucks way more than the slightly dorkier look of me in a hat vs without.

Bucket hats are my go to.

I need maximum sun protection. I used the classic salt water fishing caps for years. This is about 1999, before my beard turned grey.

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