Timeless Headwear: A Comprehensive Guide to Different Styles of Men’s Hats

Hats are timeless accessories that never go out of style. They elevate your outfits with a touch of sophistication and serve practical purposes, offering protection from the elements and adding a distinctive flair to your style. Whether you’re seeking protection from the sun, warmth during the colder months, or simply aiming to make a bold fashion statement, the right headwear can be your ultimate accessory. 

Among the array of styles, British heritage hats have long been celebrated for their timeless elegance, practicality, and superb craftsmanship. Flat caps are known for their sleek, rounded shape and small, stiff brim; trilbies offer a more modern twist on traditional headwear, featuring a narrow brim and a slightly indented crown; and newsboy caps exude vintage charm with their rounded crown and buttoned peak. Read on to explore the rich history, diverse styles, and practical benefits of these enduring fashion staples. 

Fedora

When it comes to stylish British country hats, the fedora stands out with its distinct design and rich history. Its crown is creased lengthwise down the middle and pinched on both sides at the front. This classic shape gives it its signature look. The fedora has an intriguing past, often linked with gangsters and the Prohibition era, which was when it reached the peak of its popularity, spanning from the 1920s to the early 1950s. It was a staple in the daily attire of many American men until JFK, a fashion icon himself, started showing up in public without a hat, sparking a 40-year trend of hatlessness. 

A quality felt or straw fedora comes with a sturdy yet flexible brim. This versatility allows you to snap the brim up or down at the front or back. You can mould it to achieve that perfect, slightly askew look. Whether you’re dressing up for a formal event or heading out for a casual day in the countryside, the fedora adds a touch of timeless elegance and a hint of nostalgic charm to any outfit. 

Who Made the Fedora Famous?

Did you know that the fedora is also known as the “Borsalino”? This name comes from Giuseppe Borsalino, the talented milliner who gave the fedora its contemporary shape. His version of the hat became the flagship model for his brand. The fedora’s fame skyrocketed in 1900 when it won a prize at the Universal Exhibition of Paris, spreading its popularity worldwide. 

Trilby

Trilbies are another type of British heritage hats worth mentioning. They feature a shorter, narrower brim that angles down at the front and turns up at the back, unlike the fedora’s wider and flatter brim. The trilby also has a slightly shorter crown compared to the typical fedora design. This hat reached peak popularity in the 1960s, largely because the lower head clearance in American cars made wearing taller headwear impractical while driving. However, it started to fade in the 1970s as men’s headwear went out of fashion altogether. The trilby made a brief comeback in the 90s with boy bands and some musicians, but in recent years, it’s become more associated with nerd culture, particularly the cheaper versions made from synthetic fabrics. Despite this, a well-made trilby can still add a touch of classic charm and sophistication to your look.

Pork Pie

The porkpie hat is another classic piece of stylish British country headwear. These caps are instantly recognizable by their narrow brim, which is always turned up, and its flat top with a circular indent. Fashion writer Glenn O’Brien once humorously noted that the porkpie is the mark of a determined hipster, the kind you might spot hanging around a jazz club or a pool hall, often paired with a goatee, soul patch, or toothpick. 

Boater

The boater is a quintessential men’s summer formal hat made from stiff sennit straw. Its defining features include an inflexible brim, a flat top, and a wide grosgrain band, often striped or solid black for traditional formal occasions. Think of it as the summer equivalent of the homburg in terms of formality. You’ll often see boaters paired with blazers, smart lounge suits, or even black tie. The boater adds a touch of classic elegance to a summer formal outfit, making it a must-have for those looking to channel a bit of timeless style. 

Newsboy

The newsboy hat, often referred to as a flat cap, was the quintessential working man’s accessory during the early 20th century. From the 1910s through the 1920s, it was a staple for men and boys across all classes, though it was particularly common among the working lower classes. You could find these hats UK wide – on newsboys hawking papers, dockworkers unloading cargo, and even high steel workers labouring high above the city streets. They adorned the heads of shipwrights, costermongers, farmers, and artisans, not to mention their appearance on beggars and bandits in the stories of that time. 

Photographs from the era capture their widespread use, while novels and films from and about that period frequently feature this iconic headwear. The flat caps weren’t just practical but also a symbol of the hardworking spirit of the time. Their enduring charm and historical significance make them a classic piece of British country style, bridging the gap between practicality and timeless fashion. 

Driving Hat

The Ivy cap, often confused with the newsboy cap, is a classic style of headwear that has its roots in Southern Italy, Northern England, and parts of Scotland. Unlike the newsboy design, it features a sleeker design without the floppy eight panels or the button on top. It boasts a remarkable number of names, reflecting its widespread popularity and regional variations. You’ll hear it called everything from a cabbie cap to a scally cap, or a driving cap, and even a cheese-cutter in England and New Zealand. In Scotland, it’s known as a bunnet, while in Wales, it’s called a Dai cap. 

Traditionally, this type of headwear is crafted from materials like wool, tweed (the most common choice), and cotton. Although less frequently, you might also find them made from leather, linen, or corduroy. For added comfort and warmth, the inside is often lined, making it as practical as it is stylish. Whether you’re driving, golfing, or just enjoying a leisurely stroll, the Ivy cap remains a versatile and fashionable choice. 

Beanie

The beanie is a classic when it comes to keeping warm and cosy. Typically made from wool or cashmere, this hat shields your head from the cold. While it’s great for warmth, it’s not the best at keeping your hair neatly in place. The beanie’s straightforward design and snug fit make it a reliable choice for chilly weather, ensuring you stay comfortable without fuss. 

Anabel Cooper

Anabel is a graduate of King’s College London and upon graduating, she set out on a journey to inspire and empower women through her words. Besides working as a digital marketing expert, Anabel is a freelance copywriter.