Men have always dominated the hat wearing scene. Sure, there was a time when the streets were crawling with sun hats and the church-pews were strewn with different variations of the turban and those fascinators which were notorious for causing a nuisance; but between the fedora, bowler and Panama hats alone, bros have always played the field in an elegant but effective sun-blocking manner. So, let’s take a deep dive into the world of best men’s hats!
Finding the Right Hat for the Occasion
You’re never fully aware of just how many types of hats there are until you are rummaging through a sea of safari’s, bowler’s, trucker caps, beret’s and cowboy hats, and you find yourself wondering if style and sun protection is all that important.
Well, seeing as you would put similar effort into finding the best polarized glasses for men or men scarves (yes, we said men scarves), we can all agree that style and sun protection are a part of our daily function. Thus, making a decent effort at finding the best men’s hats is not merely negligible; sorry.
There are at least 25 different (known) hat styles, with some styles having different variations. Unfortunately for the fashion-impaired, these hats also have varying functions and cannot simply be worn without thought.
That’s right dads. Just because it keeps your balding patch nice and toasty, doesn’t mean dad-hats are a general function fashion-accessory.
But it’s not just the dads that are found defaulting in terms of what hats to wear, where. Between the duckbill and ascot caps, the gambler and the homburg hats, and the Panama and bucket hats, it gets a little tricky; even for the experts.
Here are a few hat types and a brief insight into their appropriate function:
Boater hats add a great, whimsical touch to any summer outfit. They gained popularity in the 19th century after becoming a staple accessory for sailors and cruise passengers, and are essentially straw hats embellished by a band ribbon.
If you garnish this piece with one of the best sunglasses for men, you’ll probably have a hard time getting people to stop looking at you with admiration.
An iconic design, the bowler hat is alternately dubbed the ‘derby hat’ for obvious. It is designed to be a short brimmed, hard felt hat with a round top. It adds a touch of class to formal wear – and if you’re looking to be a little costume-y, it can spruce up your outfit to the derby.
Pair this up with a three-piece suit and one of your great bowties for men, and you could very much be on your way to starting a fashion revolution.
Never mind that soldiers and fisherman have basically co-opted this design to be part of their uniform. This wide-brimmed cotton blend hat (usually) makes a great outdoors companion, regardless of your profession. Those brims mean that you’ll never have to worry about getting sunburned again – of course, it also means that you’ll look a little goofy, but we are all about being different right?
Other types of hat include the lifeguard, paperboy, Aussie hat, Panama hat, steampunk hats etc.
Choosing the Best Men’s Hats for You
Much like hairstyles and tactical gloves, hats are designed to favor some face shapes over others and to serve varying protective functions. If you are looking to fancy up that fairly-attractive mug of yours, here are a few tips to consider;
The most significant aspect of your hat choice is the symmetry it gives your face. While short, fuller faces will do well with a fedora or Panama, those options may not suit bros with a similar facial structure as Orlando bloom – a square, boxy shape.
Think about your complexion and Hair Color
You want a hat that stands out no doubt, but nobody wants a hat that draws attention to itself and makes them look that a white-washed hat stand that simply displays the object of interest.
The underlying rule here is simple; darker tones blend better with deep colored hats and brighter tones with green or brown. If your skin looks like it could use a little sunlight, stick to gray and dark blues.
Match your clothes
Your outfit mustn’t be matchy-matchy to be great; however, every accessory must blend in nicely with your clothes, and ultimately complement each other. Gray, brown and black hats
The Unspoken Rules of Hat Wearing
Resist the urge to sit down to dinner with your gorgeous locks tucked beneath that ‘one-of-a-kind’ hand-knitted beanie; just like you won’t settle into a family meal with those men’s leather gloves on your hands or your key holder on your pinky. Trust us, people aren’t looking at you because they love the accents of color in your boater hat. Once you cross the threshold of a building, it is considered impolite/unsophisticated to leave the hat on your head.
Beyond taking off your hands indoors, taking them off on select occasions (whether outside or inside) is considered a gesture of respect. They should also be removed while singing an anthem, during weddings, funerals and related events. Remember to also put them on a hat rack or to hold it to your side or your chest with the under-brim facing you – nobody wants to see that scalp sweat or grease lines.
Our Top-most Recommended Best Men’s Hats
Rather than filter through a slew of overwhelming options, here are a few recommendations you can select from;
Barmah Hats Canvas Drover
It doesn’t have the formal elegance of a boater, nor does it boast the rugged DNA of the cowboy hat; but if these two types of hats somehow got together and made an Australian baby, that baby would likely be an Australian outback hat like the Barmah Hats Canvas Drover .
The Barmah Hats Canvas Drover is an Aussie made from a blend of materials and construction similar to that of the boater and cowboy hat. And there couldn’t have been a better match. Between its cowboy-hat-like brim and crown, providing excellent UV protection and the airflow allowed by the mesh sides quite similar to the boater, the Canvas Drover makes an excellent companion for just a simple day in the sun or a dicey tour of the outback.
Topped off by a chin cord that secures the Drover in place, and a hat sizing kit that’ll come in handy, this hat will no doubt, make an outback lover quite happy.
- Mesh construction supports breathability
- Water resistant cotton canvas
- Comes with hat sizing kit
- Large brim and added materials provide UV protection
- It is not very shapeable so sizes are tough to reduce or augment
- Has a small tendency of developing pinch points at strange parts of the crown
Barmah Hats Canvas Drover Hat 1057BE / 1057KH / 1057BR / 1057BL – Beige – Large
- Premium Durable Poly Cotton Canvas – comes with FREE Hat Sizing Kit
- Air Flow Through Mesh Sides – Wide Brim
- Chin Cord – Sun Protection Liner at Front
- Water Resistant – 50+ UV Protection – Lightweight
- Brim: Side 3″ – Front 3″ – Back 3″ – Crown: Height 4 1/8″
Bailey of Hollywood Men’s Curtis
The Bailey of Hollywood Men’s Curtis is an exquisite safari fedora, guaranteed to add an elegant touch to formal wear and make an excellent partner if you’re simply looking to waltz into the bar for an informal hoe-down.
It mostly validates the well-known fact that you cannot go wrong with a fedora; much less a wool-felt breed with a sun blocking turn-down brim and a pinch front that will leave you looking like the most sophisticated man in the room.
Between its signature shape which is popular for being crushable, its water-resistant form and its comfort sweatband layered by its unique grosgrain trim of Japanese origin, this bad-boy is an elegant way to stand out without breaking a sweat; not to mention, with its unique unisex construction, the Curtis will certainly make an excellent icebreaker.
A hat that makes you look great and reels in good company? Well, don’t mind if we do.
- Soft, wooly texture
- Water-repellent construction
- Crushable – and yet, retains shape.
- Can alternate between various seasons
- A little too pricey compared to the alternatives
- The crown of the hat is reportedly shallow for smaller heads.
Bailey of Hollywood Men’s Curtis, Grey, Small
- DESIGNED WITH LITEFELT: This hat has been crafted with LiteFelt, a revolutionary treatment process that takes a natural unstiffened premium wool felt hat and makes it water repellent and shape retentive.
- PERFECT FOR EVERYONE: The Curtis LiteFelt fedora is one of our best selling styles for both men and women due to the low profile pinch front crown and generous 2 1/2″ turn down brim. The Japanese grograin trim makes the style simple and versatile.
- CRAFTED FOR COMFORT: This fedora is finished inside with a comfort sweatband that is lightly padded, thus absorbing moisture and is comfortable on the forehead. The laster etched Bailey wordmark logo is placed minimally at the bottom of the back bow edge past the crosspiece.
- STYLE AND SOPHISTICATION: Bailey has become known for bringing style and sophistication to functional wool felt fedoras. Our shapes, brims, crowns and colors all contribute to assuring the man or woman that wears it will attract attention and effortless confidence to their look.
- RICH HERITAGE SINCE 1922: Bailey encapsulates “What’s On Your Mind” with the evolution of traditional hat designs that reflect a Western heritage and iconic Hollywood “Golden Age” glamour. Bailey delivers integrity, craftsmanship, and sophistication with every hat they make.
Harley Davidson Men’s Joy Baseball Cap
If you are looking to find a good old baseball hat, you are in good company. No doubt you won’t be bringing this along to date night or wear it to that formal office party, but nothing will see that you’re well protected from the sun like the Harley Davidson Men’s Joy Baseball Cap ; and if you are a dad looking to spruce up their ‘soccer-dad’ look, this might just be the option for you.
Let’s begin with the fact that this cap is made of soft and cushiony cotton which will keep your head safely tucked in, and perhaps warm when need be.
Its back closure is adjustable and guarantees that your bad-hair-day is tucked safely away from civilization (yeah, we know why you’re always wearing hats).
Add that to its embroidered dealer name and side patch, and you have a cap that delivers on its promise to leave you feeling like a bad-ass.
- Made of 100% cotton
- Adjustable and can fit just about anyone
- Crushable & Packable
- Unique Harley Davidson embroidery
- Baseball caps generally have limited uses (Unlike formal options)
- Crown is a little shorter than some might prefer
HARLEY-DAVIDSON Men’s Joy Ride Bar & Shield Baseball Cap – Black BC05230
- Harley-Davidson joy ride baseball cap
- Features our Wisconsin Harley-Davidson dealer name embroidered on back
- Made of soft 100% cotton
- Embroidered Bar & Shield side patch
- Adjustable back closure
Tilley Endurables LTM6 Airflo Hat
Tilley Edurables are popular for making hats that ‘go with anywhere’; and their Endurables LTM6 Airflo hat does just that.
This hat is an outback design with a ¾ sized mesh around the crown and a medium brim whose function is enhanced by UPF sun protection and the dark under-brim. Suffices to say, when it comes to sun and glare protection – the LTM6 has you covered. Not to mention, that ¾ mesh and hydrofoil sweatband guarantees sufficient aeration along with the protection provided.
Combined with its 100% cotton material (which, by the way, is machine washable) and moisture-wicking material the Airflo hat makes the excellent adventurer’s companion. And all this, with a back wind cord which helps to secure the hat when the wind comes roaring.
If you add protection, ventilation, convenient maintenance (thanks to a seamless synthetic wax finish) and wind resistance, you basically have a the Endurables LTM6 Airflo hat – topped by a whimsical design and unwitting charm – really, what else could you want in a hat?
- Crown mesh and hydrofoil sweatband allows ventilation
- Unique back wind cord secures hat in place even in strong winds
- Includes secret compartment for stowing away small valuables
- Easy hand or machine wash
- Wrinkles far too easily
- Significantly smaller than most outback hats
Tilley LTM6 Airflo Hat Natural / Green 73/4
- Guaranteed for life not to wear out; Insured against loss for 2 years – all perils; 50% deductible
- Excellent sun protection, rated UPF 50+, the maximum rating given; Repels rain, floats and ties on in the wind
- Brim size: Front: 3 1/2″ Back: 3 1/2″ Sides: 2 1/2″; Weight: 4 ounces
- Fabric: 100% supplex nylon (Nylamtium), mesh from 100% polyester
- Machine wash delicate or hand wash. Re-shape by hand. Air dry. Do not bleach. Wash it frequently or non-removable sweat stains will mar it and possibly rot it.
Outdoor Research Helios Sun Hat
A boonie with a prominent drawcord is basically the identifier of most serious-minded wanderers/adventure seekers. However, it’s not that we don’t all like baseball hats, on a good day, a fedora and two-piece makes a great statement, but there’s very little you can get done in the great outdoors, if you are clutching onto a cowboy hat for its dear life – and that is where hats like the Outdoor Research Helios Sun Hat comes in.
If you’re looking for something rugged and built for the outdoors, you aren’t likely to find a better fit than the Outdoor Research Helios Sun Hat . Comprising 86% and 14% nylon and polyester respectively, this sun hat is essentially rip proof – especially considering it’s brim floats are also stuffed with foam to improve stiffness. Along with its Solar-Shield construction and TransAction headband, it is easy to see why this sun hat is considered a great outdoor option.
- Lightweight (even though it’s brim is foam stiffened)
- Pull cord secures the hat and readjusts the fit
- Made from a rip-proof nylon and polyester blend.
- Some people do not appreciate the rigidity of the foam-stuffed brim
- Not much is done to waterproof this hat – and for the outdoors?
Outdoor Research Helios Sun Hat, Khaki, Large
- Fabric Performance: Water-Resistant, Breathable, Lightweight, Wicking, Quick-Drying, TransAction Headband, UPF 50+
Kangol Men’s Tropic
No, you don’t have to be part of a string-quartet or work in a barbers-shop to own a good old ivy hat. They are basically the sleeker, flatter version of the school-boy which we can all agree is an all-time favorite. I mean, the school-boy might be a veteran, but he sure knows his way around facial symmetry and so does the ivy – and the Kangol Men’s Tropic gives credence to the fact.
From its unique blend of high-quality polyester and acrylic to its comfy but stretchy nylon-made headband, the men’s tropic will give anyone a dapper look, while doing a great job of shielding your face from sunburn.
…And the best part?
It goes with virtually anything.
Unlike the bowler that is limited to formalwear and the baseball that can’t be worn to a formal dinner. This hat cuts across the board and then some. It goes dancing with friends on Friday night and still sits on a serious looking suit on a Monday. And if you are ever stuck in the woods without a sunhat, it does a great job of fitting the bill.
Try testing the limits like that with a bowler hat.
Okay, you probably shouldn’t.
- Versatile and stylish
- Elastic sweatband for sizing and sweat management
- Constructed with a fairly indestructible blend.
- This hat runs a little large – especially for smaller framed people
- The sweatband is reportedly flimsy.
Kangol Men’s Tropic 504, Black, Large
- AUTHENTIC HEADWEAR: The Kangol Men’s Tropic 504 flat cap gets its name from the number assigned to the original block shape that it is made on.
- AN ICONIC IVY CAP: The iconic 504 shape has become a staple for the Kangol brand the style of which perfectly frames all face shapes while complimenting all features.
- COMFORTABLE STYLE: Fitting in the same way as our vented 504 cap this non-vented version gives a clean and sharp look that differentiates it from its iconic brother-and its Tropic yarn means that the hat is lightweight and comfortable.
- COOL VERSATILITY: Worn by top designers professional athletes and movie stars alike this versatile classic cap looks good on the street and in any stylish scene.
- BORN BRITISH RAISED ON THE STREETS OF NEW YORK: Kangol is a cultural fusion of British heritage the birth of hip-hop and cutting-edge street fashion producing innovative products since being founded in 1938 England.
Dahlia Men’s Wool Blend Knit Beanie
Whether it is keeping those bald patches nice and toasty or hiding your identity while you are breaking and entering, a beanie is essentially the ultimate fall/winter sidekick.
Fine – breaking and entering is a heinous crime and we do not recommend it. However, in terms of the warmth that the Dahlia Men’s Wool Blend Knit Beanie provides, we do not rescind our earlier statement. The Wool blend consists of high-quality wool and acrylic blend complete with a lining made from velour, guaranteed to keep your precious mug warm on a chilly day. And at almost 9 inches high and up to 9 inches wide, it’ll certainly fit just about any head size and may even be dragged down below the ears.
Needless to say, any hat that fits that snuggly will certainly have no wind resistance trouble. To top things off, it is fashionable and can seamlessly alternate between formal and informal functions.
- Snug, one-size-fits-all design.
- Comfortable wool blend and inner lining
- Versatile in terms of functionality.
- Velour might be a little itchy for those with extra-sensitive skin
- Might leave too much room, depending on the size of the head of the wearer
Dahlia Men’s Wool Blend Cable Knit Beanie, Velour Fleece Lined, Dark Gray
- Measure: Flat measurement is 8.5 inches high and 9 inches wide at bottom
- Made of high quality wool blend with soft acrylic
- Classic knitted cable pattern with comfortable and super soft velour lining on the inside to keep you warm in the cold winter
- Available in Black, Dark Gray, Light Gray and Burgundy
- Risk-Free Shopping: quality assurance in addition to a no-question-asked return policy
Carhartt Men’s Acrylic Watch Hat
Anybody with an eye for fashion will agree that a Carhartt is an all too familiar name in hat making. And while we recommend the Dahlia Men’s Wool Blend Knit for anyone in the hunt for a great beanie, the Carhartt Men’s Acrylic Watch Hat serves a similar purpose for people who prefer their cold weather hats a little closer to a skullie than a beanie. And if Velour doesn’t sit right on your skin – this might just be the hat for you.
The Carhartt Men’s Acrylic Watch Hat unlike popular blends is made from 100% acrylic and is identified by its unique sewn-in Carhartt label (which is essentially a reassurance of quality). It is designed to fit just about any head size and is sure to secure your noggin in its warm, stretchable fabric that is both comfortable and unlikely to cause any itching or skin reactions.
- Made with 100% acrylic (unlikely to cause itching)
- Stretchable design that will just about fit any noggin’
- A little snugger than the typical beanie.
- Crown is 13 inches long (which might be a little too long for smaller frame faces)
- Not exceptionally warm especially in lower temperatures
Carhartt Men’s Acrylic Watch Hat A18, Black, One Size
- Carhartt Company Gear Collection
- Carhartt label sewn on front
- 100% Acrylic
- Stretchable;The crown length is 13 1/4 inches
- Hand wash only, do not bleach
Henschel 5310 Packable Mesh Breezer Hat
There’s nothing like a fine mesh hat on a crisp, warm day to keep the sun-rays at bay and the air coming in – and the Henschel 5310 Packable Mesh Breezer Hat is everything we ever wanted in a mesh hat and then some.
Let’s begin with the fact that this baby is actually made from cotton. Not those frustratingly itchy raft materials, or polyester-wool blends that often hinder aeration – but cotton. It is also composed of UPF material which is particularly valuable in sun protection.
Like its name, the Breezer hat supports free breeze circulation with its mesh design which is unlined on the exterior. It also features a sweatband that tackles sweat-beads generated by the wearer. Along with being a great hat for warm days, it also makes a great traveling/hiking companion on windy days – with a soft, lightweight brim and an adjustable chin cord that secures your hat in place, you’ll never have to be unprotected on sunny days, ever again.
Not to mention, with its crushable form, complete with a self-band that holds the Breezer together, stashing it your luggage will be no bother at all.
- Composed of UPF material
- Made from cotton
- Mesh design supports air circulation
- Lightweight brim and overall form.
- Adjustable chin cord secures hat in place
- Sizes run a little too large (medium sized noggins’ take note)
- The sweatband might be a little uncomfortable for those with sensitive skin.
Henschel Aussie 5310-Earth Hat,Earth,Medium
- Completely packable
- Classic 3″ Brim
- Self Chin cord
- 55 percent Polyester and 45 percent Cotton
Stetson Men’s 6X Open Road Fur Felt Cowboy Hat
When all else fails – a cowboy hat does not.
And no, cowboy hats aren’t only made for country guys with ambitions far bigger than their hometowns, but every man needs a cowboy hat. Especially fur felt designs like the Stetson Men’s 6X Open Road which is, by all means, one of the best options available.
The open road rancher by Stetson is essentially a pace-setter when it comes to fur-felt cowboy hats. In a world full of straw, wool and polyester designs, this bad-boy offers a cushiony, luxurious alternative; one, which has been tested and tried by the likes of former presidents Johnson and Truman.
Between the classic cowboy look that it endues, its comfy fur-felt feel, and it’s reassuring durability, there is no doubt that this will make someone a very happy cowboy in the making.
Plus, everyone knows Stetson always raises the bar in hat making – there is no denying that this bad boy is no different.
- Cushiony, fur-felt material
- Classic cowboy look and feel
- Hand-crafted & durable
- Unlike other designs, it doesn’t come with a storage box (logistically, this can be pretty frustrating)
- Sizing gets a little tricky when it comes to length.
Stetson Men’s 6X Open Road Fur Felt Cowboy Hat Silverbelly 7 1/8
- Classic Rancher Look That Never Goes Out Of Style
- Choose a genuine fur felt hat for better quality and long-wearing durability
- Proudly crafted in the U.S.A.
It will take a lot more than a few thousand hours to exhaust the discourse on the best men’s hats. Truth is, there are just as many great options as there are terrible ones. Meaning that the market is crawling with options that will have you rethinking every last option.
If you ask us, any hat that provides you with the kind of comfort that you need per time should undisputedly make the rank of the best men’s hats. Of course, no one hat can be all that for you. On some days, you’ll need the whimsical ‘country-ness’ of the Stetson Men’s 6X Open Road Fur Felt Cowboy Hat and on others, you’ll beg for the warmth of the Dahlia Men’s Wool Blend Knit Beanie . When it’s sports season the Harley Davidson Men’s Joy Baseball Cap might make a great podium companion, and if you ever need a wingman at a formal event, the Barmah Hats Canvas Drover will make a great choice.
At this point, it won’t be out of order to simply ask you to buy one of everything on this list, but the only person that truly knows what you need is you.
And so, we have to ask – which of these hats seem like what you need the most?
Don’t worry, take your time…
Or just choose the Kangol Men’s Tropic and be done with it.
Just kidding, take your time…