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Looking for a "Goldilocks" hat

Having toned up & lost a fair bit of weight over the past year I've started to take my clothing a bit more seriously. While I occasionally have to wear a suit at work most of the time it's quite a casual environment. Most people, myself included, wear jeans but I'm starting to add chinos & other cotton pants to the rotation. For tops it's usually striped or patterned oxfords, occasionally a sweater or vest. Shoes are anything from wingtips or bucks (usually suede) to ankle boots. Outerwear I definitely lean to 3/4 length barn or field jackets, walking or pea coat. To summarize a lot of stuff in my closet comes from Orvis.

With the return of the cold weather I want to up my hat game and am looking for some advice. No baseball caps (those are saved to cover helmet head), cowboy hats (I like them, often wear one out at the cabin but IMO not for the city), while they look good on some other guys I've never been attracted to the bowler, newsboy, flat caps or pork pie styles and trapper or kromer are a bit too rustic. So I think that pretty much leaves something in the fedora or trilby families. A true fedora or trilby is IMO too formal of a look for what I'm after and something like a waxed cotton "Indiana Jones" or outback style is too casual. Wanting to keep brim to under 3.5" and the crown around 4" to 4.5" here are some I think have potential.

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So, first question. Not that I really care but I'm vain enough to want to know are hats "back" or am I going to look like George Costanza?

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Now more substantive questions. Based on what I've described for my taste in fashion are the samples I've posted above on mark? Too casual, too formal? Color, three of the four are black. That's clearly the safe classic choice but what about something dark/darkish green or brown? And is there a different style of chapeau that I should consider?

Oh, I'm 50 so want to look like neither a hipster or a grandpa.
 
Being a 50-something I was a latecomer to the whole "wearing a hat" thing. Never thought I looked good in a hat until I tried a trilby that caught my eye. Now I have a little collection of hats that pretty much cover any season, occasion, color scheme, and mood.
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I am off to a "celebration of her life" for my wife's aunt, who just passed recently. I will be wearing the black hat on the far right with the little plume of feathers. The color scheme of the feathers very nicely complements a Calvin Klein sport jacket with a crushed velvet finish. Blue dress shirt from BOSS, a pair of off-white Khakis, and a pair of Bull Boxer Cognac leather side-zippered boots with white soles and I am good to go.

Tim
 
I guess the hat look depends where you live and where you are going........ and of course how you look wearing one...so it's a very specific fit and look.
 
Having toned up & lost a fair bit of weight over the past year I've started to take my clothing a bit more seriously. While I occasionally have to wear a suit at work most of the time it's quite a casual environment. Most people, myself included, wear jeans but I'm starting to add chinos & other cotton pants to the rotation. For tops it's usually striped or patterned oxfords, occasionally a sweater or vest. Shoes are anything from wingtips or bucks (usually suede) to ankle boots. Outerwear I definitely lean to 3/4 length barn or field jackets, walking or pea coat. To summarize a lot of stuff in my closet comes from Orvis.

With the return of the cold weather I want to up my hat game and am looking for some advice. No baseball caps (those are saved to cover helmet head), cowboy hats (I like them, often wear one out at the cabin but IMO not for the city), while they look good on some other guys I've never been attracted to the bowler, newsboy, flat caps or pork pie styles and trapper or kromer are a bit too rustic. So I think that pretty much leaves something in the fedora or trilby families. A true fedora or trilby is IMO too formal of a look for what I'm after and something like a waxed cotton "Indiana Jones" or outback style is too casual. Wanting to keep brim to under 3.5" and the crown around 4" to 4.5" here are some I think have potential.

View attachment 1045705 View attachment 1045706

View attachment 1045707 View attachment 1045708


So, first question. Not that I really care but I'm vain enough to want to know are hats "back" or am I going to look like George Costanza?

View attachment 1045718


Now more substantive questions. Based on what I've described for my taste in fashion are the samples I've posted above on mark? Too casual, too formal? Color, three of the four are black. That's clearly the safe classic choice but what about something dark/darkish green or brown? And is there a different style of chapeau that I should consider?

Oh, I'm 50 so want to look like neither a hipster or a grandpa.

All four options are classic and would look great with the right outfit IMO!! :thumbup: :thumbup:

I have long since given up following the most current fashions as I only have to please myself and especially LOTH! This is the great advantage of getting to a certain stage in life!
 
I would wear any of those four hats. I wear a hat every day, and I have for decades. After I moved to Seattle and was shortly thereafter prescribed eyeglasses, I quickly deduced that wearing a hat would keep the drizzle off my eyeglasses. Then I decided that I enjoyed hats. I've got 32 hats hanging on hat racks on the wall in the living room, and another couple of dozen stashed elsewhere. None are ball caps, and only one is a flat cap. All the rest have brims.
 
I wore a Scala for years, and now I wear a Pendleton. If it's not that, then it's a jeep cap, because I love those, or if I'm up on the mountain it's a Himalayan style.

Scala is nice because they're affordable IMO, and have a lot of nice colors, shapes, models, whatever you want to call them, and the one I had came with fold down ear flaps, which are great for windy days and riding.
 
Stetson was great until their quality dropped off in 1962. Later, they were bought out by Hatco in order to remain solvent. Your best bet is to buy a "bespoke" (custom-made) hat. You can purchase an excellent bespoke hat from Mike Miller at Northwest Hats (www.nortwesthats.com). They're not cheap but will last the rest of your life. (The reason you buy a hat is for real wear, not just a fashion statement).

JB Stetson's "Boss Of The Plains" was his "original" Western hat. Mike Miller can make a hat that can be passed down for generations.
 
I wear a Tilley hat daily. I even had a coworker refer to it as a "signature hat" for me. While I highly enjoy them, I do find them to be a bit pricey. Only because I've noticed them getting stained by my sweat, so the "lifetime" guarantee gets ruined (for me) by staining.
Regarding if hats are "in", I can't help you there. I wear it because my family has a bad history with skin cancer, and I like to reduce the amount of sunlight when I'm out. It has the added benefit of keeping my ears/neck from burning and keeping the rain off my head.
 
Thanks for the link! A fun browse.

www.northwesthats.com. (You left the "h" out!)
Sorry about that, Chief. Mike Miller is one of the best in the business. If you want something cheap, you can buy any hat, anywhere. If you want quality at a reasonable cost, Mike Miller is the best way to get more "bang for your buck".

With proper care, his creation(s) will last a lifetime and on through your children's lifetime.

I don't receive any compensation from Mike in any way, shape, or form. I just wear his work as a satisfied customer.
 

tankerjohn

A little poofier than I prefer
I’m curiously if @Canadian Mountain Man found a hat he likes. Please share!

If I knew in 2019 what I know now, I’d encourage the OP to have a look at Akubra’s lineup for the type he wanted. Great quality and value. Good range of styles for town or country.

As to whether hats are “back”? Definitely not. Hats - full brimmed hats, at least - are an outlier. But I tell you what - when I wear my hats, I am greeted by far more smiles and compliments than awkward stares or snarky comments. I think the keys are wearing a hat that compliments your face and shoulders and is harmonious with the rest of your outfit. A hat should be very intentionally worn. Then, just wear it with confidence and observe basic etiquette like taking it off in church and for the National Anthem, and you’re off and running.
 
I’m curiously if @Canadian Mountain Man found a hat he likes. Please share!

If I knew in 2019 what I know now, I’d encourage the OP to have a look at Akubra’s lineup for the type he wanted. Great quality and value. Good range of styles for town or country.

As to whether hats are “back”? Definitely not. Hats - full brimmed hats, at least - are an outlier. But I tell you what - when I wear my hats, I am greeted by far more smiles and compliments than awkward stares or snarky comments. I think the keys are wearing a hat that compliments your face and shoulders and is harmonious with the rest of your outfit. A hat should be very intentionally worn. Then, just wear it with confidence and observe basic etiquette like taking it off in church and for the National Anthem, and you’re off and running.
Seeing this post pop up but didn’t look at the year. I was going to recommend Akubra Banjo Patterson. Get your hat size from a local Lammles and order from Australia. Best factory produced hat on the market.
Johnny
 

tankerjohn

A little poofier than I prefer
Seeing this post pop up but didn’t look at the year. I was going to recommend Akubra Banjo Patterson. Get your hat size from a local Lammles and order from Australia. Best factory produced hat on the market.
Johnny
Excellent! Yes, the Banjo is precisely the model I had in mind. Looks great with just about any casual outfit while also plenty robust for hard wear in the out-of-doors. For sizing, I have found my Akubra to fit the same as my modern Stetson, so that’s at least a starting point. I’ve heard not all Akubra models fit the same; it’s probably worth doublechecking with the retailer on sizing recommendation for a specific model. Also, Akubras are known to “shrink to fit” and some people suggest going up a size and using foam in the band until sun, rain, and sweat works it’s magic to dial in the fit.

For the spirited hatwearer not averse to hand shaping an open crown, I would also - somewhat immodestly - recommend the Campdraft, which, like the Banjo, strikes that nice balance between rugged and stylish. I am exceedingly biased; my Campdraft is my favorite hat. Like a good boar brush, it continues to evolve and get better with use. However, while I find imperfectly hand bashed crowns charmingly rakish, I understand they are not everyone’s cup of tea.
 
There are many styles of fedora including some nice brown colors that go well with barn coats. The flat cap is another tried and true style.
 

Tirvine

ancient grey sweatophile
Yes, it's an older thread but still fun. I wear a Tilley T3 and toss it in with a load of laundry regularly. I am thinking about an Open Road, maybe two, straw for hot weather and Silverbelly for the cooler seasons.
 
I prefer a good felt hat over waxed cotton. Nicer look for office and around town. You might look at Bailey Hats. USA made, good quality.


I have had one for many years. Does well in the rain too.
 
I still stand by Akubra as a great choice. Here are two web pages I have personally ordered from
The Banjo Paterson is my first recommendation to people looking for a less formal hat with a moderate crown and brim. But as you already seem to be a hat wearing you probably have a feeling what brim size and crown shape you look good in.
Hope that helps
Johnny
 

oc_in_fw

Fridays are Fishtastic!
Having toned up & lost a fair bit of weight over the past year I've started to take my clothing a bit more seriously. While I occasionally have to wear a suit at work most of the time it's quite a casual environment. Most people, myself included, wear jeans but I'm starting to add chinos & other cotton pants to the rotation. For tops it's usually striped or patterned oxfords, occasionally a sweater or vest. Shoes are anything from wingtips or bucks (usually suede) to ankle boots. Outerwear I definitely lean to 3/4 length barn or field jackets, walking or pea coat. To summarize a lot of stuff in my closet comes from Orvis.

With the return of the cold weather I want to up my hat game and am looking for some advice. No baseball caps (those are saved to cover helmet head), cowboy hats (I like them, often wear one out at the cabin but IMO not for the city), while they look good on some other guys I've never been attracted to the bowler, newsboy, flat caps or pork pie styles and trapper or kromer are a bit too rustic. So I think that pretty much leaves something in the fedora or trilby families. A true fedora or trilby is IMO too formal of a look for what I'm after and something like a waxed cotton "Indiana Jones" or outback style is too casual. Wanting to keep brim to under 3.5" and the crown around 4" to 4.5" here are some I think have potential.

View attachment 1045705 View attachment 1045706

View attachment 1045707 View attachment 1045708


So, first question. Not that I really care but I'm vain enough to want to know are hats "back" or am I going to look like George Costanza?

View attachment 1045718


Now more substantive questions. Based on what I've described for my taste in fashion are the samples I've posted above on mark? Too casual, too formal? Color, three of the four are black. That's clearly the safe classic choice but what about something dark/darkish green or brown? And is there a different style of chapeau that I should consider?

Oh, I'm 50 so want to look like neither a hipster or a grandpa.
All look good, but if I were picking I’d go either #1 or 3 (though the feather would have to go, in my case).
 
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