What Men’s Hats Are In Style

What Men’s Hats Are In Style

What Men’s Hats Are In Style

Wondering what men’s hats are in style in order to grab one and make heads turn your way?

Well, here’s an insider’s guide to knowing what’s hot and what’s not! New Year, is a good time to bid adieu to old fashion trends of the past, especially when it comes to super chic men’s headgear. You will be spoiled for choice in 2020 as this Season’s men’s hat fashion trends give you oozing masculine appeal and style. Some of them are old-time classics that have returned after decades with a bang while others are maverick woolen beanies, smart baseball caps and other comfortable headgear like tweed hats that never go out of style. If you are fond of men’s hats and looking for the top 2019-2020 fashion trends to upgrade your closet today, check out our top style recommendations for super chic men’s headgear that not only dominated the major fashion runways at Milan, New York, and Paris recently but are here to stay till the end of this year.

What Hats Are Popular Now?

Before you start shopping for men’s hats, it’s imperative that you find out what men’s hats are in style. You must choose hats that naturally syncs with your lifestyle, wardrobe, head shape, and facial features. Check out our hat guide to get an idea of the different types of men’s hats.

Are Men’s Hats Back in Style?

Men’s hats never went out of style and the only thing that changed is their designs. Here’s a list of top trending men’s hat styles for 2019-2020 along with suggestions on how to accessorize them on a bad hair day-

1. Trimmed Straw Grosgrain Panama Hat

Trimmed Straw Grosgrain Panama Hat
Showing a straw Panama hat

This classical style men’s hat comes in one size fits all variants. Generally made of straw or grosgrain. Recommended for its high -quality weaves and super comfortable internal browband. Check the hat out at Amazon to grab some amazing summer deals!

2. Snapback Cap

Ideal for contemporary wear and keeping you cool in the hot summers especially if you are an ardent baseball fan. Made of cotton and available in one size fits all, these monochrome colors give you a smart grown-up image. You can check out high-end fashionable snapback/baseball caps created by ace designer MCQ Alexander McQueen or you could just visit Amazon if you are looking for inexpensive daily wear caps. If you are fond of bright and vibrant hues, check out Fresh Prince to spoil yourself to glory!

3. Tweed Flat Caps

Tweed Flat Caps
Showing a golf flat cap

Perfect for Fall and Winter – Keeps you warm as generally these caps are made of wool or alpaca. Again, it is a one size fits all headgear. Some come with integrated ear flaps for extra protection against cold weather. Check out Lock & Co Hatters for the latest high-end fashion styles.

4. Fedora Hats

Fedora Hats
Showing a black fedora hat

A classic piece that never goes out of style. Available in different sizes. Made from wool but inexpensive for everyone to afford. The diverse range of colors and a must-buy for men of all ages. If you want the best of glamour on an affordable budget, check out Amazon for amazing styles in light tan hues to bluish greys

5. Woolen Beanies

Woolen Beanies
Showing a lady with a hat for chill weather made out of wool

Ideal for casual wear and available in all sizes. They are made from grosgrain or wool. Choose from a wide range of styles. If you are looking for high-end fashion choices, check out some super elegant styles by Gucci. These beanies are soft to the touch and luxurious in appeal. Besides, this iconic designer house, you will find many kinds of beanies from Steve Zissou to Jimbo Jones. If you are searching for affordable options, Amazon is your place to go.

6. Trilby


Often mixed up with the Fedora, this hat is made from tweed or straw. You often see them at horse-racing events as it is the hot favorite of the upper class. It features a taller crown and smaller brim than the Fedora. It is perfect for Spring and Fall. This hat should be worn at the back of the head and is often flaunted by Boy Band music groups. Justin Timberlake is a great fan of the Trilby as he flaunts them a lot in his public appearances and music videos. For trending Trilby Hat 2019-2020 check out Jacobson Hat Company or Amazon.

Men’s Hat Styles 101

Here’s a million-dollar question: Are men’s hats back in style this year?

Men’s hats have been around since the 1600s and were once considered high style accessories in the British Royal Court. Right from the tricorne to the pith helmet and modern baseball cap, hats have always been used to make key fashion statements. The 19th and the 20th saw the evolution of several kinds of men’s hats like panamas, fedoras, derbies, boaters and popular cloth hats.

Fast forward to 2020, you may consider why you should consider adding a couple of stylish men’s hats to your closet? Present ace fashion designers say men’s hats are in vogue this year. In fact, some of these classic hats are the ones that your grandfather might have worn back in the days. Besides style, the following are 3 reasons why you should don a men’s hat for a given occasion –

1. Hats Are Functional

It’s true we live in a comfortable world now with central heating and air conditioning. However, when you go out, men’s hats are not only a fashion accessory. They keep the weather elements out of your face. They keep you warm in cold winters and cool in the hot summers. So, men’s hats are functional pieces that go beyond just the style quotient. Here’s our guide to find the best winter hat!

2. Hats Ooze Style

Back in the 1940s, 1950s and 1960s men everywhere were wearing hats so it was safe for them to wear one. However, today, you need the confidence to pull it off as most likely, you might be the only man at a gathering wearing a hat. However, this is a bonus point for you especially if you have the know-how on how to sport the right hat with the confidence needed to create the right personal style statement. You should wear a good men’s hat if it helps you to stand out in a crowd provided you have the courage to be able to do that.

3. Hats Give a Message

Have you ever wondered why police officers, military personnel or men in authority wear a hat? They send out a signal of power and that is a great thing. Besides this signal of strength, hats make you look taller. Any man wearing a hat gives out a perception of added height. There are many men who would like to look taller so wearing the right hat adds to that!

Buyer’s Guide for Men’s Hats

Before shopping for the latest trending men’s hats for the season, check out the following 5 things

1. Material

What is the hat made from? Is it made from wool, straw or felt? Choose the right hat for the season.

2. Shape

The shape of the hat will determine the style.

3. Size

Make sure the hat fits you. If you wear a hat that is too big, your face will look small. If you wear a hat that is too small, you will end up looking comical.

4. Quality

Is the hat made by a machine or is it hand-made? Would you pick up a hat at Target for $12 or would you choose a hand-made hat by iconic designer houses like Gucci? There is a huge range for you to choose and play around with for the right look. However, work with a professional stylist if you are serious about buying quality men’s hats for your wardrobe.

5. Price

Last but not the least, price determines how you wear the hat. You could spend $20 on something and wear it once or you could spend $120 on a hat that you love and wear it 100 times!

Know What Hats Are Popular Before Buying

Now that you are ready with the know-how on how to buy men’s hats, let’s check out what hats are in style 2019?

1. The Fedora Hat

Always has been an iconic style in classic men’s hats. It can be molded to the wearer’s taste.

2. The Trilby

Showing a Trilby hat

It is shorter than the Fedora and has the brim snapped down to give you a narrow-angle at its back.

3. The Homburg

Wool Felt Homburg Hat
Showing a black felt homburg cap

It is the dressier sibling of the Fedora and a safe bet for the formal business look. It has a stiffer brim.

4. The Pork Pie Hat

Pork Pie Hat
Showing a navy blue pork pie hat

This short-styled hat has a flattened top without a crease down in its center. It has side pinches like a Fedora and has a triangular like wedge-shaped front.

5. Derby or Bowler

Bowler Hat
Showing a bowler cap for men

This is one of the easiest classic men’s hats to recognize by everyone. Though often sported by the upper class in Britain, it actually has humble origins. It belonged to the working class and has a stiff dome with a crown.

Contemporary Styles to Sport This Year

1. Newsboy Cap

Newsboy Cap
MG Men’s Plaid Ivy Newsboy Cap Hat

It differs from the flat cap as it has puffed up corners like the ones you see in the epic British Gangster TV series Peaky Blinders. It’s a throwback from the 20th Century British society.

2. Snapback Baseball Cap

Snapback Baseball Cap
Showing a black baseball cap

Popular among the Yankees, the snapback cap protects your face from the sun and gives you more versatility. If you prefer a clean look, go for the flat rimmed with high crown caps for getting a new era style. Check out some cool caps at Lids.com/MLB.

3. Beanies

They are a must-have Fall-Winter essential for every man’s closet. Super trendy and functional to keep your face warm.

4. Bucket Hats

Bucket Hats
Showing a Bucket Hat

These hats are a massive trend for Spring/Summer 2019-2020. Check out some super chic bucket hats in comfortable materials at Hats.com/Bucket-Hats.

5. Docker Hats

Docker hats are top trending hats this year. It’s not common and more of a stand-out choice for men if you dare to be different in a crowd. Choose from a wide range of docker hats at Assos.com/Docker-Hats.


Research is the best way to know what style will suit your face, personality, and image. Get inspirations and ideas from fashion bloggers online on how do men wear hats style? You will get some amazing tips and wearing advice from them.

Since the last 40 years, hats have relatively gone into obscurity with the exception of the baseball cap however in 2020, classic men’s hats have returned in a big way. Perhaps men want to start dressing with a purpose like they did in the past. They no longer want to pay attention to their outfits or their shoes, they want more attention and this is where men’s hats step in to fulfill their desire.

Men’s hats are an amazing way to add depth and dimension to any outfit. However, they are more than just matching them to a cool shirt and pants. If you want to up your style game with men’s hats, the trick here is to experiment with a large range of hats and coordinate them with the perfect accessories.

In order to rock, all you need is the confidence to choose the right one for your personality and image. Pair them with formal or casual outfits to hit the road and transform good style into great style in no time!

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