men wearing hats

Blast From The Past: Men's Hats That Are Making A Comeback

Published: 10/03/2021

Hats are perhaps the most essential accessory in any man’s wardrobe arsenal. Versatile, chic and functional, they add that crucial sense of je ne sais quoi to every ensemble, no matter the weather or season. Even in the UK’s most unpredictable of climates, you can always rely on a hat to keep you looking stylish and protected, effortlessly completing any outfit in a subtle yet striking way. Yes, come rain, hail, snow, or shine, this most hailed of headwear will never leave you out in the cold… or heat for that matter! From baseball caps to buckets, trucker hats to trilbies, there really is no better way to enhance your attire than with a beautiful bonnet. 

Here at OnBuy, we want to remind you of fashion’s most popular hat styles across history, and determine why they’re making such a storming comeback in 2021. Unlike lycra, shoulder pads and leg warmers (thank you, 1980s), these most appealing of appendages have certainly stood the test of time, remaining relevant and trendy for decades.


The timeless Trilby

trilby mens hat

First debuted in 1894 during a stage adaptation of George du Maurier’s novel Trilby, this stylish hat is among the most ageless of accessories in minimalist elegance and refinement. Traditionally crafted from rabbit hair (now usually leather or felt), the Trilby features a small brim, tall crown and angled front, perfect for anyone looking to add class to their clothing. Though not particularly functional, they can be worn as a statement fashion piece in spring and autumn combined.

Popularised by the inimitable Frank Sinatra in the days of classical Hollywood glamour, it’s hardly surprising that the Trilby has recently come back into fashion. With its memorable shape and simple design, this hat is the perfect embellishment for any formal outfit or occasion, and will keep you looking smart and polished in even the most relaxed of settings. 

Still often sported by celebrities, the likes of Justin Timberlake included, the Trilby hat has proven to be one of the most consistently ‘modern’ adornments across time, and understandably so. After all, who are we to question the man that, quite literally, brought sexy back?


The fashion-conscious fedora

fedora mens hat

Move over Indiana Jones, it’s not just you who loves the fedora. From gangster staple in 1920s to hipster headgear in the 2000s, this chic chapeau has never gone out of fashion… and that’s not about to change! Why not jump on the fedora revolution? We promise you won’t regret it. 

From film noir to Freddie Krueger, Mad Men to Michael Jackson, there simply hasn’t been a time where this hat hasn’t crept into some form of popular culture. Like the Trilby, history is full of examples of men who have donned this ageless bonnet with casual flair and sophistication, and it’s easy to see why. Commonly made from wool, straw, or cotton (or cashmere for the more boujee among you), fedoras are characterised by their soft brim, indented crown, and pinched teardrop peak. In terms of decoration, small feathers, belts, and funky prints are also occasionally added to enhance the feel of luxury, and why not? They’re pretty customisable. 

Today, this firm-brimmed hat is once again on-trend among the famous and the fashionable. Channelling their inner Humphrey Bogart, actors like Johnny Depp and Brad Pitt have regularly been known to fine-tune the fedora, adapting it to suit their own contemporary styles. 

Whatever your opinion on hats (and trust us, they’re often the most polarising of men’s accessories), you can’t go wrong with this one.


The humble beanie

mens beanie hat

Once a mere winter essential, beanies have now become truly trans-seasonal pieces. Though you may not be inclined to wear one in the middle of summer, you can pretty much rock this casual hat from the autumn to the spring. Indeed, it won’t just leave you feeling warm, it’ll keep you looking hot, too! 

Across time, beanies have often been associated with alternative movements and, with our love of everything vintage today, it’s hardly surprising that these cosy caps are suddenly making a comeback. Available in a variety of colours, shapes and patterns, they are perhaps the most versatile of hat styles on the market, suited to a number of climates and occasions. From understated rhombus models to niche, breathable designs, they’re a fundamental part of any man’s closet arsenal, and shouldn’t be ignored as the true accessory that could really enhance your wardrobe. Look to Harry Styles and Jake Gyllenhaal as inspiration for this one – they’ve certainly mastered the look!

If you haven’t already, it’s definitely worth investing! We recommend a plain black number as the perfect place to start your beanie journey.


The dorky dad hat

dad cap hats

Love it or hate it, the dad hat is a vintage accessory that just screams laid-back style. Though your dorky dad may not be the best person to take fashion advice from, this hat should certainly not be ignored. They make great additions to any sports-luxe ensemble and can be used to bring a vintage twist to any casual look or outfit.

Contrary to what the name might suggest, dad hats are essentially a variation of your classic baseball cap, featuring wide, circular crowns and curved, stubby bills. First promoted by the New York Knickerbockers baseball team in 1849, they’re actually one of the oldest styles on this list, and remain one of the most indispensable items in any man’s summer wardrobe. Usually made from a polycotton blend, with the option of embroidered detailing in a variety of eye-catching colours, they’ll keep both your head and wallet protected for the long-run. Think Adam Sandler: relaxed yet somewhat trendy. This is the look that dad hats can help you to accomplish – chic and easy-going fashion.


The not-so-new newsboy

newsboy hat

First emerging in the 19th century, these old-school caps have experienced a raging revival this decade, and it’s not hard to see why. Similar to a flat cap, newsies often consist of a stiff peak and rounder panelled body, occasionally adorned with a button on the brim. Gracing the heads of fashion-conscious men for hundreds of years, they’re the smart-casual trimming you didn’t know you needed.

Thanks to a number of popular British period dramas (Peaky Blinders, we’re looking at you!), the newsie has become one of the most prevalent hats worn among celebrities today. From David Beckham to Jason Momoa, Daniel Craig to Ashton Kutcher, there aren’t many A-listers who haven’t donned this timeless headpiece. Flaunting well-groomed charm as well as rugged appeal, the newsboy cap is extremely versatile and flexible.

From patchwork, to herringbone, to tweed, there are thousands of designs and materials available, great for those who like to change their style on the fly. With other variations including wool, leather and even canvas, there really is no end to the looks you can create. 

Give way Thomas Shelby, there’s a newsie rebirth on the horizon!


Cap-italise on your caps

gents headwear

We hope you’ve enjoyed this blast from the past, reflecting on some of history’s most popular recurring styles. If you’re searching for a combination of comfort and charm, look no further than OnBuy’s online selection of the top men’s hats making a comeback this year. 

Or, if you’re in need of something more detailed, why not browse our guides on the Top 6 Men’s Trapper Hats or Most Fashionable Baseball Caps for 2021. Whatever your budget and style, there’s certainly something for everyone.

Please note: the information in this blog is correct at the time of publishing but may be subject to change.



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