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11 Best Hats For Men to Wear On Every Occasion (Caps Included)

Hats off (pun intended) to the men who correctly top off their outfits with an appropriately matching hat. Traditionally, hats have mostly served a functional role. For instance, keeping your head and ears warm during winter months or shielding you from the furious beams of the glaring sun in summer.

Increasingly, men’s hats are becoming a great way to accessorize an outfit. The combination appears stylish, even if you’re not the fashion-obsessed type.

That aside, hats also serve some particularly peculiar roles. From concealing an emerging bald head or receding hair to acting as a face disguise especially in collaboration with sunglasses or a facemask.

Best Hats for Men 11 Best Hats For Men to Wear On Every Occasion (Caps Included)

With all these roles, it’s worth taking the time to find a worthy headpiece for your daily use or for that special occasion, whichever the case may be.

But before we delve into the best hats for men, let’s consider what makes a hat great wear.

Is there such a thing as the right hat?

Choosing the right hat can, surprisingly, be challenging, even for men of studied elegance.

It’s quite convenient to simply reach for the classical baseball cap to quickly cover that overgrown hair as you leave the house. But you can inject a little more variety into your closet with a whole range of hats. And the options are numerous; Panama hats, bucket hats, top hats, pork pie, snapback, boater, winter beanies, and many more.

Men’s hats were customarily a subject of stringent rules and regulations. Rules not based on written laws but just social norms. Nonetheless, a disregard for these rules was not taken kindly.

A classical example of this is when a three-day riot ensued in New York City in 1922 over a dispute regarding straw hats. Then, men only wore straw hats in summer and took them off by 15 September to be replaced with woolen hats. Someone tried to go against the grain of social norms, hence the New York’s Straw Hat Riot.

Today, wearing an inappropriate hat is no longer a matter of grave consequence. That said, it helps to dress up as that stylish man with a desirable sense of panache by selecting a befitting hat.

A great hat needs to be versatile so as to serve you in multiple situations. For warmer weather, such as you’d experience when out hiking, a lightweight, breathable hat made from absorbent material would be fantastic. That would keep sweat from flowing down your brow as it allows for the circulation of air on your head. It would be awesome if the hat comes with a strap.

Certain hats are for ceremonial functions. Headgears such as the boater and the top hat are best used during celebratory functions like weddings.

Types of hats for men, based on face shape

Not all hats work the same on all faces. A hat that looks elegant on someone else might be unimpressive on you. Learning to match your face shape to a hat type can prove to be a major breakthrough in the journey to picking the best hat.

Faces fall into six primary shapes: oval, round, heart-shaped, diamond, long, and square.

In which category do you fall?

  • Long faces go well with hats with wide brims and cut across the forehead to downplay the seemingly long face structure. Beanies are not ideal for long faces. Cowboys and sunhats will do a fine job.
  • Square faces have a way of emphasizing an angular facial structure. Wide-brimmed or floppy hats are a great set-off for squarish faces.
  • Round faces come out best in angular hats that de-emphasize the rounded facial feature. Flat hats and Fedoras are best for round faces. If you must wear beanies, pull them low over your face.
  • Heart-shaped faces come out well in caps that diminish the slimness of the jaw and the broadness of the upper face. Go for fedora, newsboy, flat cap, or baseball caps. Floppy brims are a big no as they end up accentuating the upper face that’s already wide.
  • Diamond-shaped faces have a narrower jawline. How you wear a hat on this head is even more important than the hat itself. A pork-pie that features a shallow crown will do. Grab hats that you can work with further back the head.
  • For an oval-shaped face, anything goes. The choice is in your hands.

Our Top 11 Selection Of The Best Hats For Men

When it comes to picking the best hat, you might be spoilt for choice owing to the multitudinous options available. Top off your look with these fashionable, outstanding hats that make our top 11 list of best hats for men.

1. Columbia Bora Bora Booney Hat

Columbia Bora Bora Booney Hat 11 Best Hats For Men to Wear On Every Occasion (Caps Included)

Best for weekend warriors who like being on the hiking trails, mountaineering, or kayaking.

Stylish and functional, this dad hat from Columbia has a wide brim that provides perfect cover from the scorching sun. But it does more than shield you from the sun, it’s made to protect you from the harmful UV and UVB rays that cause sunburns and pose a long-term danger to the skin. The manufacturers made this cap’s tight weave out of yarns that absorb UV rays and keep you safe.

You’ll remain cool and dry, thanks to that hat’s efficient moisture management. The hat uses Omni-Wick, an advanced technology to rapidly eliminate moisture that forms on your skin and spreads it over the hat fabric. As the moisture evaporates it leaves a cooling effect on your body. Cool, huh?

Moreover, the hat is made to fit all. It’s fitted with a versatile drawcord and toggle to adjust according to your desired fit. A durable and fashionable hat that will be a feather in the cap through your outdoor adventures. It’s available in several colors including beet red and a nearly-black hat.

2. Scala Men’s Dress Straw Laichow Braid Boater Hat

Scala Men’s Dress Straw Laichow Braid Boater Hat

Scala’s Dress Straw Laichow Braid Boater Hat is great for summer and ranks as one of the best hats for men that sets the mood for celebration. You can wear this hat in multiple ways; sport it on with a matching tropical shirt, or bring out a flat-crowned version with a light-colored outfit.

This is a classic boater hat that gives you the sophistication of yesteryears. Its popularity soared from the late 19th-century till the early 20th century. It’s made of tough straw with a ribbon running along the circumference of the crown. This chic design of a hat is flat-topped with wide brims. It’s perfect headwear that can make you sand out this coming summer.

At the apex of the popularity of boater hats, they signified the onset of summer, and a Straw Hat Day was commemorated. Put it on to relive the good old days.

3. Marmot Retro Cotton Trucker Hat

Marmot Retro Cotton Trucker Hat

It’s one of those fashion items that keep making a comeback, time and time again. Marmot is highly reputed for making high-quality gear to beat the cold weather. This hat is just as durable. It’s great to wear for the outdoors. The front is cotton-padded, while the sides and back have mesh, making it breathable as the air easily flows through to cool you down whatever the weather.

With the adjustable snap closure, you can size it to fit your head. The cap is sturdy enough to maintain its shape as you pack it for transport due to its 6-panel construction. The best bet for a squint-free summer outing lies in Marmot’s Trucker Hat. The embroidered logo elevates the fashion-sense of the hat that adorns an excellent classical look.

4. Sunday Afternoons Havana Hat For Men

Sunday Afternoons Havana Hat For Men

Ideal for travel, you can easily fold and cramp up the Sunday Afternoon Havana Hat into some pretty tiny spaces. Whatever festivities arise in the cause of travel, you just pluck it out and you’re ready to party. Goes well with pastel trousers and a buttoned-down shirt. It features an internal Wicking Sweatband that manages moisture well helping you stay cool through the day.

Made from tough paper material, the hat is more than stylish. It also provides ultra-protection with a built-in UPF 50+sun-protection that keeps your skin safe from dangerous rays. A 2.75-inch brim keeps you well within the protection. Choose from a variety of black and tan hues to complete your leisure outing. This hat is a golden classic that’s bound to be a hit…on our heads.

5. Nike Authentic Dri-Fit Adjustable Cap

Nike Authentic Dri-Fit Adjustable Cap

This will be the cap of choice for anyone with an active lifestyle. Out and about, you’ll hardly miss the Nike baseball cap with its characteristic white Nike swoosh admirably displayed at the front. Lightweight, comfortable, and stylish, it’s as if they were just perfectly made for guys. The cap can be adjusted to fit your head size.

The hat is constructed from excellent moisture-wicking material, and it’s also breathable. The cap finds itself at home from the baseball pitch, a gym, and is occasionally sported decorating red carpet events. A hat befitting the status of a leading global brand, Nike Dr-Fit is a must-have for anyone with a vigorous lifestyle.

6. Brixton Messer Medium Brim Fedora Men’s Hat

Brixton Messer Medium Brim Fedora Men’s Hat

Brixton’s Messer will get you covered in the cold weather. Messer is constructed from 100% wool but has an accessible price tag. It features a wide variety of colors to your taste, attire, or skin-tone ranging from olive to light tan.

The hat has a medium-wide brim and a stylish complimentary leather sash going around the crown in a manner resembling a belt band. This headwear is versatile and can get you covered within the house or outdoors matching various styles whether formal or casual.

A classic design with a modern tinge. Definitely worth a mention in this list of the best hats for men.

7. Paul Smith Men’s Artist Straw Crotchet Hat

Paul Smith Men’s Artist Straw Crotchet Hat

Enjoy a cool refreshing beverage with friends on a warm summer afternoon. As you lounge and unwind, this is one beautiful hat that you’d want to have with you over a fun-filled summer.

Paul Smith’s Artist Straw Crotchet Hat boasts a wide brim and a multi-colored band that flatters the earth-colored straw that makes up this stylish hat. The Italian-made hat’s interior is padded with a grosgrain band. If you prefer navy, it also comes in that color option.

 

8. The Hat Depot Low Profile Dad Hat

The Hat Depot Low Profile Dad Hat

Constructed from six panels, the Hat Depot Low Profile Dad Hat is sturdy, giving it a firmness on the head. That said, it also packages well as it easily crumbles occupying minimal space while you travel.

This must-have baseball dad hat is designed for everyday activity, whether you’re up and down mowing the lawn or just passing the day relaxing. It’s made of pure cotton that protects you from dangerous ultraviolet rays from the sun. It’s tough enough to shield you from the sun and gentle enough to create a cozy environment for your head and scalp with its fine cotton.

The hat comes in an array of 18 colors plus an additional 22 color combinations so you can stay comfortable while wearing the colors that bring the best out of you. From its wide color scheme, you can create a fitting color match with your day-to-day attire. The buckle closure at the back of the hat makes it possible to adjust it for a personalized fit.

9. Biltmore Dijon Braid Porkpie Hat

Biltmore Dijon Braid Porkpie Hat

The Biltmore Dijon Braid Porkpie Hat is a classic hat fit for a night out. A charming hat that has a definitive flat top and a tip-tilted brim facing upwards. It’s flexible and you could snap it down at the front for an alternative look. The hat is ultra-lightweight being made from flexible straws.

It has a sleek hatband that pairs up an embroidery of cream and red cleverly combined to give the hat character and style. The double band terminates with a Biltmore pin. The hat tops off casual wear beautifully during the summer months.

 

10. Carhartt Men’s Knit Cuffed Beanie

Carhartt Men’s Knit Cuffed Beanie

A classic that you’ll be grateful to have. Made from 100% acrylic rib-knit material, Carhartts Knit Cuffed Beanie delightfully shields from the wind and cold during the chilly months. The fabric stretches out perfectly fitting all. It has the Carhartt logo elegantly embroidered on the front. Keep warm and cozy in this best-selling beanie, you’ll find it irresistible whenever the temperatures drop.

11. Kangol Men, Women Washed Bucket Hat

Kangol Men, Women Washed Bucket Hat

Kangol is a highly respected British headgear maker that has been churning out high-quality products since the 1930s. Over the years, they’ve provided headgear to all and sundry including the high and mighty such as Diana-the Princes of Whales, The Beatles, and the Scouts Association.

A Kangol bucket hat, 100% cotton, is lightweight, and perfect all-year-round. A classic hat with a rich history.

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Conclusion

One cool thing about adorning the right hat is that it can perfectly accentuate your stylish look. People wear hats for a variety of occasions and through all the seasons of the year. You’ll certainly spot something warmer for the cooler winter months and a lightweight, breathable hat for the warmer months.

Besides highlighting some of the best hats for men, we’ve shown how to choose the best hat for your face type.

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