How to choose a hat?

[FarmerTan]

How about a fedora, or a trilby which is similar but with a narrower brim. For fedora think 1940s Indiana Jones, for trilby think 1960s Sean Connery as James Bond. I would go trilby.

View attachment 1265632

I've got both types, and wear what I want, when and where I want.

My only advice is this: if you feel self-conscious, then you need to not buy that hat. Go to a place to try on different styles, like someone else already said.

Right off the top of my head I'd guess you'd FEEL more comfortable in a Trilby, since you want to be able to fit through the door.

I've got Tilley's coming out of my ears, but I rarely wear any except my wool winter one that has the fold out forehead and ear warmers. A finer looking/feeling hat is not made by ANYONE else.

 

[hairless wonder]

And if they look at ya funny tell 'em to kiss your....

Just be ready run or fight. I love being old enough to be that jerk now.

I still get to wear my cowboy hats and boots on occasion. There's a charity rodeo where I volunteer every year. It's just one weekend a year, but at least I don't look entirely out of place in my hat and boots.

Also, I sometimes wear my boots with a suit and tie. I really need a bolo tie to complete the outfit enough for me to wear my one of my cowboy hats.

 

[FarmerTan]

I still get to wear my cowboy hats and boots on occasion. There's a charity rodeo where I volunteer every year. It's just one weekend a year, but at least I don't look entirely out of place in my hat and boots.

Also, I sometimes wear my boots with a suit and tie. I really need a bolo tie to complete the outfit enough for me to wear my one of my cowboy hats.

I have a bolo tie I wear on occasion. Gets comments, here in Michigan!

 

[Lefonque]

yee-haw

 

[StillShaving]

I like the second. The first looks a little....plasticy? IDK. The second is going to be pretty close I think.

So from a normal mans perspective and not some hipster fad type thing..... is the "pork pie" hat still a thing or is that like a faux pas?

The nylon ones are smoother and tend to reflect more light in certain conditions. The darker colors show this more than a lighter color like neutral or khaki. I believe this effect is also because of the waterproof finishing, that after washing a number of times it lessens somewhat.

The ones made from cotton or hemp may be more to your liking, they are a touch more causal looking to my eye and also nice. That your choice of fabric is about the overall look and performance. For instance if you want it to dry out more quickly after getting caught in the rain and absorbing less water to begin with then the nylon is likely the best choice. I do not own a hemp version but my impression from trying one on in the store is that it was stiffer and therefore the crown might hold its shape better after being crushed or washed.

 

[Lefonque]

travelling hat at a jaunty angle 1/2 brim up. Who says that you can’t be fashion risk.

 

[DaveHStone]

Have worn a ball cap most of my life. Just cause that is what folk do around here. Small head. Never find hats that fit/feel just right. Wanting to up my hat game. Still casual enough to wear to work, around town, everyday but a nice long step above a ball cap.

Would be nice to be able to toss in washer or overnight bag (crushable I guess?) Never been a "full brim" cowboy hat kinda guy. Sorta like a brim all the way around maybe but not so wide ya bang it on doorways LOL

So my question is..... WHAT AM I LOOKING FOR? I see people mention the Tilley and have had a look at them some. Safari hat or 2. Aussie? bush hat or something like that. Bucket hat. I have seen a few that are close, but just have not found "it" yet. And all my searches seem to come up with the same hats. So I thought I might ask the ever knowledgeable B & B lol

I hear what you're saying, as I've never been a "hat person" either.

That said, I think going from baseball cap to a HAT, is not "stepping up your game", it's rather a quantum leap. And it probably won't work, as it won't feel like being yourself.

You want to find that "middle ground" and I think a flat cap is your new best friend.

See the ball cap is smth. you wear with a pair of jeans, snickers and smth. like aviator jacket, bomber jacket or plain denim jacket or varsity jacket. Hat (IMHO) warrants a suit or the most strict way of business/smart casual, which I somehow imagine is not your thing.

Flat cap is ideal, as you can wear it with jeans and snickers w/o looking ridiculous, but you can also wear it with a full suit AND everything in between. I wear a tweed one in cold weather, with my tweed jacket and the usual "middle-aged men" smart casual outfit and in summer I wear a linen flat cap with polo shirts, shorts and even on the beach.

Just my $0.02.

 

[trentr]

Very much appreciate all the input to consider.

I am hoping to head back to Tulsa this weekend. It should be a big enough town to have a hat store. 2 hrs away ugh. My trouble is A. indecisive
B. self conscious (so do not feel comfortable in ANYTHING)
C. no where close to try stuff on
D. Church is the only place I go in my life that I do not get dirty! LOL

Been a farm boy all my life. Work in a foundry/machine shop. Play in the woods and on a Harley. I want to dress nice, as it makes me feel good about myself. However I end up taking my nice shirt or sport jacket off and working on someone's vehicle in the parking lot of church or restaurant LOL

It took me a few years (idk 15 haha) to finally work into wearing a sport coat/jacket. It only took a few months for everyone's shock and confusion to wear off and stop making comments "Are you preaching today?????" No I just wanna look nice. I have a couple that I quite like and feel comfortable (as I can be) in. So in just a few years I should be able to work into a hat

At least all these adds on my computer are now trying to steer me into one. Stupid internet spying on my typing....

 

[trentr]

I've got both types, and wear what I want, when and where I want.

My only advice is this: if you feel self-conscious, then you need to not buy that hat. Go to a place to try on different styles, like someone else already said.

Right off the top of my head I'd guess you'd FEEL more comfortable in a Trilby, since you want to be able to fit through the door.

I've got Tilley's coming out of my ears, but I rarely wear any except my wool winter one that has the fold out forehead and ear warmers. A finer looking/feeling hat is not made by ANYONE else.

The only hat I have these days with a full brim is a "bush hat" type cotton canvas or something. I wear it mostly fishing and when I do, I snap the sides up to the crown so it only has "brim" in the front and back . Sticking out the sides just bugs me LOL

When I wore a felt "cowboy" hat as a kid, they always teased me about a 10 gallon hat on a 2 gallon head. I am a small man with a small head and just sorta need to shop in the kids section I guess haha

 

[trentr]

I still get to wear my cowboy hats and boots on occasion. There's a charity rodeo where I volunteer every year. It's just one weekend a year, but at least I don't look entirely out of place in my hat and boots.

Also, I sometimes wear my boots with a suit and tie. I really need a bolo tie to complete the outfit enough for me to wear my one of my cowboy hats.

I had a bolo that I wore before I started getting into "real" ties. They are great. Just go sorta simple. Not to BIG and FLASHY and big metal clanking knobs on the end LOL. Keep it simple. They look good on anybody <- opinion of corse

 

[trentr]

The nylon ones are smoother and tend to reflect more light in certain conditions. The darker colors show this more than a lighter color like neutral or khaki. I believe this effect is also because of the waterproof finishing, that after washing a number of times it lessens somewhat.

The ones made from cotton or hemp may be more to your liking, they are a touch more causal looking to my eye and also nice. That your choice of fabric is about the overall look and performance. For instance if you want it to dry out more quickly after getting caught in the rain and absorbing less water to begin with then the nylon is likely the best choice. I do not own a hemp version but my impression from trying one on in the store is that it was stiffer and therefore the crown might hold its shape better after being crushed or washed.

I feel like I would like the hemp....after 10 years of wear and 200 washes LOL. I like the worn in "used to be stiff but now soft" feel and look

 

[trentr]

View attachment 1265861
travelling hat at a jaunty angle 1/2 brim up. Who says that you can’t be fashion risk.

I think it works, but I have horrible fashion sense so do not take my word for it haha

 

[trentr]

I hear what you're saying, as I've never been a "hat person" either.

That said, I think going from baseball cap to a HAT, is not "stepping up your game", it's rather a quantum leap. And it probably won't work, as it won't feel like being yourself.

You want to find that "middle ground" and I think a flat cap is your new best friend.

See the ball cap is smth. you wear with a pair of jeans, snickers and smth. like aviator jacket, bomber jacket or plain denim jacket or varsity jacket. Hat (IMHO) warrants a suit or the most strict way of business/smart casual, which I somehow imagine is not your thing.

Flat cap is ideal, as you can wear it with jeans and snickers w/o looking ridiculous, but you can also wear it with a full suit AND everything in between. I wear a tweed one in cold weather, with my tweed jacket and the usual "middle-aged men" smart casual outfit and in summer I wear a linen flat cap with polo shirts, shorts and even on the beach.

Just my $0.02.

Not feeling like myself.... I still do not know who I am and the parts I think I have figured out, I do not rightly like. So not myself is a good thing

I thought about the flat cap thing. My reservation there is the fact that 1 guy at my church wears any sort of actual hat and it is a flat cap. So I am afraid to encroach on "his" thing and was trying to find my own LOL

But the versatility you speak of is EXACTLY what I need.

 

[vacman]

I'm a big fan of cowboy hats as well, so if I'm not wearing my Indie Jones hat, I'll be wearing a cowboy hat.

 

[Lefonque]

What ever you get wear it with pride. Learn to love whatever hat you wear.

 

[trentr]

What ever you get wear it with pride. Learn to love whatever hat you wear.

For me and my ball caps, the life of a hat seems to be
1. Spend forever picking one out
2. Ditch 5-10 before settling one 1 or 2
3. Force myself to wear them while hating them intensely
4. Wash/stomp/crumple/wash
5. After a few years when it just starts feeling like it actually belongs on my head.....rip/catch on fire/ huge grease stain/blow off under bush hog/ SOMETHING happens to force me to start the cycle over again

 

[Lefonque]

Hats for any and every occasion. Caps come in different shapes and styles. I was the Minister at my church and wouldn't be offended if anybody wore a hat or cap. You never know the person at your church may consider it a nod to there style.

 

[DaveHStone]

Not feeling like myself.... I still do not know who I am and the parts I think I have figured out, I do not rightly like. So not myself is a good thing

I thought about the flat cap thing. My reservation there is the fact that 1 guy at my church wears any sort of actual hat and it is a flat cap. So I am afraid to encroach on "his" thing and was trying to find my own LOL

But the versatility you speak of is EXACTLY what I need.

FWIW, if versatility is (also) important to you, for the price of one quality hat, you can probably get 3 or so good quality flat caps. Smth. to consider

 

[trentr]

I rather like the "cadet cap", but it is basically just a short squareish ball cap. Was hoping to push the envelope just a bit further haha

 

[ByMyBeard]

A lot of good advice on here. I also wondered about a flat cap for you as a potential option. I wouldn't worry about encroaching on the other guys "thing". If anything, you can bond with him about it. Hell, perhaps you could even see if he'd let you borrow one for a week to see if you like it? You never know. Hat shops are certainly hard to come by.

Regarding the different Tilley's, I've owned multiple versions. The first was the wide brim Hemp hat. I REALLY like it, but it is a bit heavier in really hot weather. Doesn't breath quite as well. My second was one of the nylon type, and I agree that while light weight they just don't "look" good for me. My current is actually "mashup", and in my opinion is perfect. Though being a mashup, the colors can be a little different than the images on the website.

You should probably also consider how you want the hat to FUNCTION. Is the function to cover the top of your head? Then a flatcap may be perfect. If you want it to protect your ears/neck like I did, then you'll want a wide brimmed hat. Note that I have the widest brim Tilley makes, and can still fit through single doorways without issue.

There may be some lower cost versions of Tilley's around you may consider as well. Some are concerned about Tilley shifting to China manufacturing, so that's one potential concern. My thinking, however, is more along the "do I like this" or not. You could try a low cost wide brimmed hat (think "Outdoor Research" maybe), and upgrade to a Tilley if you decide you like it.