Teach me about hats

[AZBronco]

I'm thinking of getting a hat to wear around. The only hats I've ever worn are baseball caps, so thinking about other types of hats is new to me and since hats aren't super common, I'm not sure where to start. Are certain styles more appropriate for casual wear? What should I be looking at when shopping? Can anyone point me to some good style resources?

As an FYI--I'm thinking of something like a wide-brimmed fedora, but I'm really just starting to look.

Thanks!

 

[Old-Fashioned Coughy Pot]

I like shopping online from The Village Hat Shop in San Diego. Great selection of hats of all prices and prompt shipping to me in the wilds of B.C.

 

[MrLara]

Curve the bill, don't wear it flat.

 

[MrLara]

Curve the bill, don't wear it flat.

Edit: damn it, that's what I get for answering too fast. Look up gentleman's gazette "rules for wearing hats"

 

[ByMyBeard]

As my follicle count has decreased, I've begun wearing hats much more frequently. I've really enjoyed Tilley hats, though they are pricey. But, they protect my head, ears (which are damn painful if they get burned), and since I get the wide brim, they keep the back of my neck from turning red. And when you have an accent like I do, having an actual red neck is just asking for comments.

 

[tankerjohn]

Hi AZ! I’m so glad you're interested in upping your hat game. As an avid hat wearer, here's my opinion on the various options beside baseball caps.

Flat caps - The easiest hats to wear. They are very versatile. With casual outfits, they work like ballcaps, but kicked up a notch. They look good with suits, albeit a bit retro. I think the sweet spot is from smart casual to semi/business casual. They work with just about any style, from traditional to fashion-forward. I also think they are very practical. They will shade your head in the sunshine, but are less likely to blow off in the wind and can tuck under a hood in the rain or snow.

Western hats - look great with casual outfits, particularly rugged, outdoorsy, or workwear styles. They can look costumy if worn out of context. Obviously, very practical for providing shade in the sun, but less practical in the wind and cold. And sure it will keep rain off, but get soaked doing it and you can't wear a hood over it. But still, I think they are most men's best bet for a wide brimmed hat.

Fedoras - I do like fedoras, but I think they are trickier to pull off. If you don’t do it right, they look costumy at best and douchy at worst; like a bad extra in a 90's sitcom. And be prepared for Indiana Jones jokes. However, fedoras do look good with sportcoats and suits, and I think work best on the more formal side of the spectrum.

Trilbies - Like fedoras, but maybe a little less costumy. Probably a better choice for most men. Plus, they look better with casual outfits, though bolder and more fashion-forward than most flatcaps.

Pork pie hats - definitely more fashion-forward. It helps to be a Beat poet or the upright bass player in a jazz trio. Or want to look like one.

Top hats - Unless your name is Slash or Tom Petty (RIP), I don't recommend it. On the other hand, a top hat with googles is the hot ticket for a Steampunk convention.

Cadet hats - I guess they're practical enough and common enough not to look costumy or weird. But I always associate cadet hats with extremely douchy hipsters, so I'm going to advise against them.

Berets - On paratroopers - yes! On hot girls going "in through the 'out' door" - yes! Everybody else - eh, not so much. I mean, I guess some guys can pull them off, but they mostly look kind of pretentious.

Bowlers - Don't. Just don't. Not on this side of the Atlantic.

Other cultures' ethnic headgear - Another don't. When you get to be a famous rock star like Billy Gibbons or Neil Peart (RIP), then you could try out a tasteful African skull cap, but I wouldn't go any further than that.

 

[Doc4]

I'm thinking of getting a hat to wear around. The only hats I've ever worn are baseball caps, so thinking about other types of hats is new to me and since hats aren't super common, I'm not sure where to start. Are certain styles more appropriate for casual wear?

Great question!

Flat caps - The easiest hats to wear. They are very versatile.

I was thinking the same thing ... this might be a good entry point for you, to transition into fancier headwear. It may take you a while to feel "right" wearing a fancier hat, and not (mistakenly) feel like you are wearing a costume.

So ... flat caps are the best transition and most casual, accepted, and versatile. And most are pretty cheap too ... inexpensive, that is ... so you don't break the bank.

Pork pie hats - definitely more fashion-forward. It helps to be a Beat poet or the upright bass player in a jazz trio. Or want to look like one.

If I wore one, it would be to look like I'm in The French Connection.

Unfortunately, I suspect I'd end up looking like I was from The Railrodder.

 

[FarmerTan]

This is a great topic, in the sense that it proves we are all different, or at least in two camps.

I cannot pull off a flat cap, because it just plain makes me feel "unconfident" if that's a werd.

I can do Tilley hats, of which I have too many, but my go to is the Fedora. Or a Panama hat in the summer.

I wear ball caps doing outdoor work or shooting guns, with ear protection which gives me sun protection as well.

If you FEEL like you are wearing a "costume" you will probably look like you are! Rocking a hat is mostly about confidence for me.

 

[Doc4]

I cannot pull off a flat cap, because it just plain makes me feel "unconfident" if that's a werd.

The berd is a werd, so now this is too.

If you FEEL like you are wearing a "costume" you will probably look like you are! Rocking a hat is mostly about confidence for me.

Indeed, that comfort level needs to be there. Or at least, achieved sooner rather than later. I suspect that any significant change in one's "standard attire" will result in some self-awareness and self-consciousness issues at least briefly, as one becomes accustomed to "the new look".

 

[Old-Fashioned Coughy Pot]

Just found The Railrodder on YouTube. Thanks @Doc4

 

[AZBronco]

Thanks for all the insights. I decided to try a flat cap as a good casual entry point.

 

[MrSpeedy]

This thread has inspired me to get a cap for fall and winter (already have a summer one). Think I will likely get an Ivy cap. Thanks to @Old-Fashioned Coughy Pot for the recommendation of The Village Hat Shop, and thanks to @tankerjohn for his excellent primer on the different types of hats.

 

[TexOkie Shaver]

On my first visit to the dermatologist years ago, she asked me what kind of hat I wore. When I told her none, she said, “If you like your ears and want to keep them, get a hat.” Years of skin abuse exposing it to the sun has taken its toll. I’ve had more actinic keratosis taken off than I can remember. I’ve also had one squamous cell carcinoma cut out and I’m going back on Monday with what I think is another.

The Village Hat Shop in San Diego is a great place to get a hat. if you can find what you want there, you probably aren’t going to find it.

I have a large straw hat for working in the yard, a gray fedora for wear with a suit, a black Stetson Gambler crushable for dark casual clothes and a brown Stetson Mountain Sky crushable for light colored outfits.

I really like the crushable hats because they are comfortable and nearly indestructible.

 

[Alacrity59]

Tilly Airflow for garden work. Need to protect my ears. I generally like the Tilly hats as you can throw them in the wash mostly. I've got a broad brimmed rain/snow hat made of Harris Tweed I really like for late fall early/mid winter. Some hats take a bit of wearing before you get comfortable / confident with them. But as TexOakie mentions . . . there are really good reasons to wear a hat that protects.

 

[FoolishMortal]

IMHO, a fedora should be worn with a suit - no less. Don't be the guy wearing jeans, sneakers a trench coat and a fedora.

Just do your best to (a) match the hat to the outfit in terms of formality and (b) wear what makes you happy...and (B) trumps (A).

 

[AshleyC]

Somebody once opined that Sinatra was the only guy under 40 who could convincingly wear a fedora. I would add to that Harrison Ford...but for the rest of us mortals, the fedora comes off as a pretentious affectation.

I wish we lived in more enlightened times, but ours are the times of casual dress at funeral visitations.

 

[Davidkimberly]

As an avid hat wearer I strongly recommend finding a quality hat shop and trying on as many different styles as possible. Find one you feel comfortable in.
For guidance check out "Kevin from JJ Hat Center" on YouTube. Kevin has worked at JJ Hats in New York for 25 years. JJ is widely considered the best hat shop in the country (although I prefer Meyer the Hatter in New Orleans).

 

[CPTdeLos]

I'm in my mid-thirties and wear fedoras often. Always with a decent shirt and a nice coat or jacket. Stick with subtle colors: grey, brown, navy, dark green/olive.

 

[Tirvine]

I love baseball caps for keeping my head warm and for keeping the sun out of my eyes, but I find it a bother to slather my ears in sun block. So I usually grab a Tilley T3. My son in law loves the Stetson Open Road, but then we are all in Texas. I love Homburgs, but they are very dressy, and I would feel pretty weird most days dressing to match my hat. Panamas are nice, but they do not offer as much sun protection as others.

By and large it is a far more casual world, and Tilleys fit in so well. pick your hats for your climate and the way you usually dress. In this online shopping era I highly recommend Holland Hats for selection, price, and service.

 

[KrstGor]

My vote goes to the Flat Cap.

Tweed one in the winter and linen one in the summer. Can't go wrong with those.

Beauty of the Flat Cap is its versatility, you can wear it with virtually anything.

It will be a great fit with a tweed sports coat, jeans jacket, leather jacket, long coat, suit, you name it. The summer one you can wear with beach clothes as well as any semi-formal or casual outfit.

I can't think of any other headwear that you can wear with basically everything.