Hats For All Occasions – A Guide For Men Who Don’t Wear Hats

“You know what’s the rage this year? Hats.”

Hobbes may have only narrowly missed the mark when he uttered that line after butchering Calvin’s haircut. The truth is that hats will never again be “the rage”. This isn’t 1947. But he was right about hats always being stylish and practical.

Even from a very young age I have always loved wearing hats. All the coolest characters from my childhood wore hats. Honest John. Darkwing Duck. Indiana Jones. Even Raphael’s seemingly untouchable coolness leveled up when he donned a fedora and trench coat when slinking around NYC incognito.

Here’s the thing, though: I realize I am in the minority. Most modern men aren’t used to wearing hats that aren’t baseball caps. Which is fine. I am not in the camp that thinks that wearing a baseball cap is infantile. But there are usually better choices in most circumstances. A baseball cap is great for keeping the sun out of your eyes, but that’s really where their utility begins and ends. Add in the fact that they are strictly casual, and you have a pretty limited piece of headwear.

And I get people’s reluctance to wear anything but a ball cap. No one wants to be “the hat guy”. Most of us just want to wear what we wear and not have people comment or make a fuss about it. But let me put your mind at ease. As someone who wears some sort of hat pretty much every time I leave the house, I can tell you that no one really cares. Most style sites will tell you that to you “just have to own it” and “don’t care what anyone thinks”! But we can’t control our feelings like that.

So permit me to give you permission to wear a hat. As a grown man with kids, you naturally have the gravitas to wear pretty much anything you want. If you were 20 years old and stumbling around trying to find your way in the world, then the “just own it” advice would be applicable. But you’re a man. You arrived long ago. You’re literally responsible for the lives of others. Do you want your kids to know you felt self-conscious about something as insignificant as wearing a hat? What kind of confidence would that instill in the beings who depend on you for, you know, life? Relax. No one will bat an eye at your hat.

Ok, enough blather. Let’s get on with it.

When I thought about how I wanted to structure this article, I thought it would be most helpful to arrange it by scenario, instead of by hat type. If you are new to hat wearing, you, dear reader, can more readily see yourself in particular circumstance than if you were just scrolling through various types of hats and how to wear them. You might sail right past, say, a fedora or newsboy cap, immediately discounting it without ever seeing when and how it might be the perfect choice.

Home – This is the most basic. If you had one hat hanging by the door, what should it be? It should be a hat that can pull double and triple duty and have you mostly covered (sorry) no matter where you’re going. Walking the dog in the rain/sun/snow. Getting some extra firewood. Running to the post office when the weather is a little dicey. Commuting to work when you know you’ll be walking twenty blocks with no shade. The hat that hangs by the door should do MOST of these things REASONABLY well. Sure, we could identify an absolute best choice for each of those specific situations, but if you want one hat to rule them all, it’s your “hanging by the door” hat. My personal choice here is the Akubra Federation IV fedora in brown. I know what you’re thinking. “You don’t want me to be ‘the hat guy’ but you suggest a fedora right out of the gate?” Stay with me.

The Fed IV is, admittedly, exactly what you think of when you think “fedora”. I will warn you, though. The Fed IV is a man’s hat. It has larger proportions than most are used to. Don’t slouch when you wear this hat. Visually, it will gobble you up. Walk tall with the confidence of knowing you look like a man who can get things done.

This hat is not inconspicuous. But that’s ok with you. The tall crown has an old-fashioned charm. It comes with an open crown, which just means it doesn’t have any dents or creases in it when you buy it. The idea is for you to crease it however you want (which is fun and not at all difficult!). If you want a crown that looks perfect all the time, then make sure you get a hat with a factory crease, like the Akubra Stylemaster. If you want a little more of a personalized look, grab an open crown hat and steam/bash as you like. The wide brim is dimensional, meaning it is narrower on the sides than it is in the front and back. I find that helps to mitigate the feeling like you’re wearing a sombrero.

The band is a more formal-leaning, wide, silk grosgrain. Many brimmed hats have a thin band, but a thin band makes the hat look a bit more casual (think cowboy hats). The benefit of the look of the brown Fed IV is that it looks fairly casual when worn with a flannel shirt and barn coat, but would also look totally appropriate with a sport coat, tie, and overcoat.

Probably the Fed IV’s best attribute is its durability. As is true with all Akubras, this thing is a tank. Akubras are made in Australia and they are built to work. Please do not be precious with your Akubra. Put it through its paces. It will take whatever you have to throw at it.

A couple months ago the family and I were driving in a torrential rain storm. It was one of the few days it was warm enough for liquid precipitation, but it was still very cold. My son got sick in the car so we pulled over and got him changed and cleaned up the backseat. I was standing outside the car for a bit as I helped him out of his clothes (he was still inside the car). Then I stood outside the car as my wife cleaned up and my son warmed himself by the front vents. If it had not been for my trusty Fed IV I would have been thoroughly soaked. My head was warm and dry and the wide brim kept the rain from running down my jacket or getting all over my glasses. I was able to hop back in the car and get on with the drive in relative comfort, largely due to my Fed IV.

Many Akubras are also remarkably affordable for the quality. I think I paid around $150 for my Fed IV and even less for my Akubra Campdraft (another fantastic workhorse).

Yardwork or Puttering Around The House – For this, you want something that is robust enough to handle dirt, sweat, and debris, but light enough in weight so you don’t overheat. A wide brim is a given considering you’ll probably be out in the sun. I suggest a Stetson Roadster. The Akubra Campdraft came in close second due to its slightly heavier felt. Cost-wise, though, the Campdraft will be about $75 cheaper than the Stetson, which is not insignificant.

The Roadster is a lesser-known Stetson model. A Stratoliner could easily be used in its place. I find that modern Stetsons get very soft and pliable with use. Much more so than my other hats. I like this attribute. Some don’t. Some want their hats to stay a bit stiff. Due to that pliability, the brims sometimes get a little wonky when repeatedly exposed to the elements. It’s easily fixed with a little steam from a tea kettle, but it really shouldn’t matter with a work hat anyway. For the exceptionally hot days, swap out the Stetson for an inexpensive Panama hat. I find the cracks that develop in the straw of a well-loved Panama only add to its appeal.

Travel – Another very broad category. Are you going somewhere warm or cold? Are you taking a car, a train, or a plane?

90% of the time when I am traveling, I opt for a tweed newsboy cap. I have mentioned before that my particular love for newsboy caps came from my dad, but their inclusion in this list is due to more than just warm memories.

I mention the newsboy specifically, but I am using that as a catch all for flat wool caps of any kind (newsboys, ivy caps, driving caps, etc). While not providing nearly as much protection from the elements as a wide-brimmed hat, where the newsboy wins is in convenience. If you are driving for a long period of time, it’s sometimes uncomfortable to have a hat brim bumping against the headrest. Not a problem with a newsboy (or a driving cap, obviously). They can also be easily stored if you’re on a plane, train, or in a restaurant. You can even sit on it if you’re really pressed for space.

The real beauty of the newsboy cap is its versatility with whatever you’re wearing. Originally, it was considered a very casual hat. Nowadays since it ISN’T a baseball cap, it feels at home with everything from jeans and a leather jacket to a suit and tie. They are also rather ubiquitous so you won’t feel out of place or look like a tourist. I’ve worn my newsboy on many trips for both work and pleasure, domestically and abroad, and I have always felt appropriately and practically dressed.

Going somewhere where a wool newsboy would be too warm? Try a linen flat cap instead. You’ll still look put together, but you won’t sweat to death. And many linen caps have UV protection.

If you’re going somewhere VERY warm where you will be out in the sun for any stretch of time, your best bet is that inexpensive Panama I mentioned earlier. I love the thought of owning a high-end Panama hat, but I will likely never be able to justify the cost. They are thousands of dollars and are not as durable as the cheap versions. My Panama is a Capas brand Bogart model. I’ve worn it on trips to Jamaica and Paris. I’ve worn it to the shore countless times. I’ve worn it to the office on those sticky NYC summer days. Yes, I have been caught in the rain with it. It’s slightly discolored and the crown is starting to crack, but it’s still going strong after being used and abused for years. I paid $110 for it.

Commuting – In the “before times” I had a very long commute into NYC which consisted of a van, a train, and a long walk. My office dress code was similar to most: Business Casual, which basically has no meaning anymore. Jeans were fine as long as you looked put together. It was mostly the women who wore jeans. Mostly chinos and dress shirts for the men. My point is that I could wear pretty much anything I wanted. I usually opted for some combination of chinos, Oxford shirts, sweaters, and sport coats. Sometimes a tie, but not always.

The hat that I determined was the best for the commute was my Stetson Temple in “Caribou” Grey. This is a fedora on a slightly less aggressive scale than the Fed IV. The crown is a bit tapered and not as tall (it also has a factory crease). The brim isn’t quite as wide. It’s much less of a statement than the Fed IV.

The felt is very soft and pliable. Given its modest proportions, this hat works for many different body types and with formal or business casual outfits. When I wear a suit, it’s my go-to hat, but it looks great with an odd jacket and trench coat, or a chunky sweater and bomber. While not considered “crushable”, its softness and factory crease insure it bounces back into shape if some dope on the train tosses his computer bag onto it when you’re not looking.  

Most importantly, the hat provides ample protection from rain and snow, making an umbrella redundant. I have found this especially important while commuting since I don’t like carrying more than I need to. It also frees up my hand so I can easily grab some coffee or a croissant or something.

Formal Occassions – I know this one is going to be a bit of a stretch for some. But if you are really decked out… I’m talking tuxedo level, here, (or even a dark suit, cufflinks, black cap-toes)… then you will want a formal (or “semi”-formal if you want to get picky) hat to match. Even a black or grey fedora will look a little too slouchy in this instance. Show the other men how it’s done by donning a black or grey homburg. You will stand out. People will look at you. Some may make a comment or two about how you look like the Godfather. That’s ok.

You hardly ever see homburgs anymore but they look absolutely incredible in the right context. The taller, squarish crown can either have a single center dent or a center dent plus two side pinches in the front. I opt for the latter out of personal preference.

Even though the homburg is a fancier hat, it is still quite practical. The thick felt traps heat well and the stiff pencil-curled brim ensures snow or rain won’t drip into your face or down the back of your neck.

My homburg of choice is a black Selentino.

A few tips on hat-wearing…

A hat isn’t any different from any other piece of outerwear. It’s meant to keep you dry and warm. So don’t worry too much about it. I see guys on online forums say they don’t wear their fur felt hats in the rain for fear of damaging them. Seriously? What else is a hat for? Hats are supposed to get wet and dirty so that YOUR HEAD doesn’t get wet and dirty.

You’ll also hear that you should always handle a brimmed hat (like a fedora) by the brim and never by the crown. While this makes sense when shopping for a hat (as in, don’t manhandle the crown of a hat you haven’t purchased yet), virtually everyone who has ever owned a hat pretty much always grabs it by the crown. Why do you think most crowns have a pinched shape in the front? It’s from people grabbing them that way. Everyone does it. Does it affect the shape of the hat? Yes. Is that bad? No. The only brimmed hats I refrain from grabbing by the crown are my Panama hat (since I don’t want the straw to crack) and my homburg (since it has a stiff brim which is ideal for handling).

Lastly, and I have said it before, do not be overly fussy with your hats. They are built from things like wool and fur and leather. They are not delicate (except for those $10k Panamas, but we aren’t talking about those). Hats can take lots of abuse. They are meant to. That’s their purpose. You wouldn’t buy an overcoat or a pair of shoes if they couldn’t stand up to use. Hats are no different. It will feel a little painful spending more on a proper hat than you would on a baseball cap. And exposing your, potentially few-hundred-dollar, new purchase to the elements can feel daunting. But don’t sweat it. They can really take a beating. At worst, give it a little steam from a kettle and some light brushing from time to time, if you are so inclined. That’s all they need.

Now go forth with your new-found confidence. Your kids will think it’s cool until they are in middle school at which point it will embarrass them tremendously for a good ten-year span or so.

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