Hats at the formal end of the spectrum waned in popularity after the War, with stylish men tending to go hatless. That’s not to say hats died out completely. Informal wear such as beanies, baseball caps and bucket hats are casual evergreens. Also, certain subcultures retained a love of more formal styles, most notably the pork pie hat that was an essential part of the 2 Tone Ska revival in the 1970s and 80s.
But now these smarter, more traditional hats are making a comeback. They’re being worn with suits and in formal settings, a nod to the more cultured look that’s regaining a foothold in the business and casual sphere. That means it’s time for a refresher on the types of hat that you’ll be seeing – and hopefully wearing – more often as the decade progresses.
Flat Cap
The flat cap is a rounded cap with a small, stiff brim at the front. Often crafted from tweed, wool or cotton, these caps suggest a blend of sophistication and practical comfort, synonymous with traditional British attire. Pair your flat cap with tweed jackets or wool sweaters for a classic, countryside vibe. They’re great for smart casual occasions.
Newsboy Cap
An interpretation of the flat cap, the newsboy cap has a fuller, rounder shape with a button top attaching the front brim. Usually made from wool, corduroy or tweed, it features a panelled crown that adds texture to the ensemble. The newsboy has a playful vintage appeal, and is good with casual blazers or robust outdoor wear.
Bowler Hat
Characterised by its hard felt fabric, rounded crown and tight brim, the bowler hat is traditionally British and was once a symbol of the middle classes. It became a hit stateside before the War, iconic on the heads of Messrs Laurel, Hardy and Chaplin. Wear it with formal suits or try mixing with modern avant-garde pieces for a bold statement.
Cowboy Hat
Typically made from felt, the cowboy hat has a wide brim and high, pinched crown. It symbolises pioneering American Western culture, but it’s also a practical piece, offering protection against both the sun and the rain. Try it with denim fabrics or tough outdoor apparel, but modern urban looks can incorporate the hat if you’re feeling rugged.
Baker Boy Hat
Graced with a puffy crown and connected brim, the baker boy is often constructed with larger panels stitched together and traditionally made in Harris Tweed or wool. It’s subtly different from the newsboy in that it’s cut to give a puffier effect, but they’re essentially the same hat with minor differences in tapering. Sport this cap with casual wear like jeans or a wool coat for an effortlessly stylish look.
Duckbill Flat Cap
The duckbill cap blends styles of both the flat cap and newsboy cap but distinguishes itself with a smoother, elongated silhouette ideal for sleek styling. The peak is barely noticeable under the front panel, but it’s there to keep the structure and to look intact. This one’s suitable for many modern casual ensembles – think sharp blazers and quality denim.
Driver Cap
Also known as a cabbie cap, the driver cap is similar to the flat cap but typically has a rounder, fuller shape and may be made from a variety of materials, including leather. This versatile cap can add a touch of vintage or working-class chic to casual or smart-casual outfits, and works well with a casual suit or just a simple sweater and jeans.
Fedora
Featuring a soft brim and indented crown, fedoras are typically made of wool or felt but can also be found in straw for summer wear. This hat is versatile enough to be worn with formal wear or as a stylish accessory to a more casual outfit. Wear it with a tailored suit for a classic film-noir inspired look, or dress down with a loose cardigan and jeans for a relaxed but refined appearance.
Trilby
Resembling the fedora, the trilby is distinguished by its shorter brim and deeper indentation at the crown. Typically made from straw or lightweight felt, it teams well with casual summer wear. You’ll find it’s perfect for summer as it’s wearable both indoors and out, offering form and function in equal measure.
Homburg
This dressy cousin of the fedora features a stiffer brim and lacks a pinch at the front often made from felt and featuring a single dent running down the centre of the crown. Its most famous wearer is undoubtedly Winston Churchill. Picture him and there’s probably a Homburg on his head. Perfect with stately, formal attire, it adds an element of old-world charm and sophistication.
Pork Pie Hat
Known for its flat crown and narrow, tightly curled brim, the pork pie hat bridges the casual/fashionable gulf perfectly. They’re usually made of wool felt to give a soft but structured finish that sets off the look. It’s traditionally aligned with jazz culture, but modern renditions pair nicely with casual suits or sharp, edgy urban wear.
Wide Brim Hat
Offering ample sun protection, these hats feature significantly wider brims made usually from felt or straw, depending on the season. Ideal for outdoor events, they’re typically worn with loose, flowing garments in casual settings or beachwear.
Boater Hat
The boater hat is a stiff, flat-brimmed hat with a rigid crown, often constructed from sennit straw and traditionally adorned with a coloured ribbon around the crown. It exudes a sharp, clean summer style that speaks of classic river outings and barbershop quartets. Pair it with summer suits or smart casual ensembles for garden parties or weddings. It’s particularly charming with striped blazers or sharp linen outfits.
Panama Hat
Originating from Ecuador, the Panama hat is made from the plaited leaves of the toquilla straw plant. It’s renowned for its lightweight and breathable properties, and features a wide brim and a high crown, making it ideal for warm climates. A natural fit for tropical holiday attire or lightweight summer suits, just ensure it complements rather than contrasts your outfit to maintain an elegant look.
Mariner’s hat
Also known as a fisherman’s cap or a Breton, the mariner's hat is often made from wool or cotton. It features a rounded crown and a small bill in front, typically styled with a braided cord over the brim. It’s beloved of artists of a certain type, and was a particular favourite of John Lennon and Bob Dylan. This one’s best suited for casual outfits – wear with a peacoat or a knitted sweater for a chilled vibe.
Baseball Cap
A staple in casual American wear, the baseball cap is characterised by its rounded crown and stiff bill projecting in front. They’re made from a variety of materials including cotton, polyester and fabric blends. Universally versatile, pair it with athleisure, casual or semi-casual outfits for an easygoing look. It’s perfect for outdoor activities or a relaxing day out, but can look off when worn with a formal suit.
Trucker Cap
Similar to the baseball cap, the trucker has a foam front section and plastic mesh back for better ventilation. It usually features a snapback closure rather than a slide buckle. Sport this cap for a laid-back working-man feel. It goes well with jeans, T-shirts, and casual button-downs.
Top Hat
The top hat is recognised by its tall, flat-crowned, cylindrical shape, traditionally made from silk or felt. It’s a symbol of 19th-century gentlemanly attire and still plays a role in formal occasions such as weddings or funerals, or with morning dress. It can have more playful interpretations, such as when you’re going for a steampunk look, but it’s an uncommon sight these days.
Beret
A soft, round, flat-crowned hat typically made from hand-knitted wool, crocheted cotton or acrylic fibre, the beret is commonly associated with artists and thinkers. However, it also has a strong military pedigree, and that has bled into its being worn by activists looking to emulate that Che Guevara vibe. The setting and situation, as well as your general demeanour, will determine whether you achieve the look you’re going for. Tilt it to one side for a classic look or wear it straight for a modern take.
Still can’t decide? Have a scroll through our extensive collection of men’s hats, perfect for jazzing up formal attire or playing it casual around the city.
