Big Hats, Bigger Style: Your Essential Guide to Styling Big Hats (2024)

A man carrying a backpack, wearing a fedora staring towards the mountainous landscape

Men’s hats were initially worn for practical reasons, but have now developed into style statements. Hats have served a variety of functions for men throughout history, from simple sun protection to serving as status symbols.

Finding the ideal partner in a relationship might be as easy as swiping right. However, with hats for men, “The One” frequently remains frustratingly elusive, especially for those still looking for it.

Choosing a hat that fits well, looks decent, and doesn’t clash with the rest of your attire can be challenging with the endless variations available. But don’t worry; this article will walk you through the best big hat alternatives for all seasons and some styling advice. You have chosen the appropriate article for larger hat styles.


Fashionable African-American man wearing a fedora. Depiction of Big Hats in Stylish Outfits.

The fedora is one of the most well-liked men’s fashion hats today. It has a long history and derives from the Greek term for “gift from God,” but since the end of the 19th century, it has been in and out of fashion.

For instance, during the Prohibition era in America, it came to be associated with gangsters. However, it’s more common to see it on creative people hiding a man’s hair underneath today.

The teardrop-shaped crown, compressed front, soft felt design, and wide brim that sits halfway between a Derby and a Porkpie make the fedora unique.

The fedora draws some criticism. But if done right, it would effortlessly give modern outfits some vintage elegance.

This type of headgear will not go well with jeans, sneakers, and a hoodie. Ensure that the one you purchase fits as you want it to. Although rocking a big fedora is a unique style, you may need to get it small enough to fit firmly on your crown if you wish to don it leaned back somewhat.

Wear it informally with collar shirts and tailored pants, or go classic with tailoring to stand out among the other men wearing suits.


They often have a rounded crown and a 2-inch short brim. Hatters make bowler hats from firm felt materials.

This hat was named after the man who created this hat in 1849, William Bowler, not after any Weekend club bowlers.

They were first designed for the working class, but they quickly attracted the attention of the elite. This hat was designed to shield the gamekeepers’ heads against falling branches while riding their horses.

The high class eventually adopted the bowler hat, notably business people operating in London’s financial area. It depicts the universally recognized symbol of the British city gent: a tall, stylish man wearing a complete suit, a bowler hat, and a walking stick.

Nowadays, young and old wear bowler hats at official events, and are about as uncommon as unicorn sightings. You can also partake in the delight. When you wear a bowler hat on your attire for your next formal event, people will be in awe of you.


A woman holding a video camera, wearing a trilby hat. Depiction of big hats, and their versatility with plethora of outfits.

The short-brimmed, sporty relative of the Fedora is the Trilby. The Trilby, frequently mistaken for the Fedora, is worn more for fashion than practicality. This design is an excellent casual substitute for the traditional Fedora since it has an angled rear that tilts over the eyes.

Every season is appropriate for wearing the Trilby. It looks best paired with playful, laid-back clothing designed for Fridays at work or a night out. Think cool men’s dress socks with a pair of pants.

Trilby can never go out of fashion. Rock it with a tuxedo to a formal event to make a long-lasting elegant impression.


The Homburg is an excellent alternative for a more formal, classic hat. The Homburg has a sunk crease, like the Trilby and Fedora. It’s a beautiful option for a formal occasion because of the cleaner profile without pinched sides. The Homburg’s brim is noticeably stiffer and curled up.

Homburg caps appeal to stricter conventional dress codes, such as those at traditional workplaces or events. They are known to be characteristic hunting caps and are worn all year round.


Couple sitting on granite rocks, wearing panama hats, taking a selfie

The Ecuadorian-made Panama hat is a traditional summer accessory that oozes style and sophistication. This thin, breathable hat, made from toquilla palm leaves, provides good sun protection while promoting airflow to keep your head cool.

The Panama hat is a crucial component of any summer wardrobe because of how versatile it is and how well it goes with both casual events and more formal situations.

Pork Pie Hat

This hat first appeared in the mid-1830s as a women’s hat, but after the turn of the century, men started wearing it too.

Its outward look is how it acquired its name. The crown is compared to a British meat pie, and has a flat top and a round pinch lining it. It also displays a brim with edges inclined upward.

Buster Keaton, a silent movie star who reportedly owned thousands of them, promoted the Porkpie. In the 1930s, college students also found it to be appealing. Although it became obsolete in the 1950s, it is now a stylish accessory for any man.

Considering hatters can make the Porkpie from various materials, such as felt and straw. If you start falling in love with this look, you can buy many outfits and the hat’s collection to wear throughout the year.

It is timeless, adaptable, and fashionable.

Choosing a Big Hat to Rock

Choosing a Big Hat

Men’s hats are stylish accessories that complete an ensemble and add character. But it’s important to know how to wear it right. It’s crucial to choose a hat style that complements your outfit and the occasion.

Additionally, you must correctly wear the hat with the brim tipped down to give off a trendy appearance. Your overall appearance may be impacted by how you wear your hat. A playful tilt can add a hint of coolness, while an upright brim expresses formality. To determine which strategy suits you the best, try out a few.

Ensure the hat is the right size for your head—not too tight or loose. Choose a color that complements your attire and rock your hat with confidence.

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