The Most Iconic Pieces Of Menswear Ever Made


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It’s a simple fact that men need to own certain items: a good hammer, a decent record player, a really warm blanket that potential mates will totally dig and, of course, a handful of tried and tested wardrobe classics.

Granted, it’s a term that’s bandied about a lot in menswear, but it takes something truly special to properly substantiate the claim.

In the search for enduring style over trends, here are some unquestionably timeless staples that look as remarkable now as they’ve always done.


Baracuta G9 Harrington

Few jackets have proved to have such wide-reaching popularity as the Harrington. Originally released in 1937 and beloved by golfers for its water-resistant fabric and ‘umbrella’ back flap, the Baracuta Harrington (or G9) went on to be adopted by several sub-cultures from skinheads to scooter boys, as well as style icons including Frank Sinatra and Steve McQueen.

The jacket took its name from Rodney Harrington, a character in the 1960s American soap opera Peyton Place, played by Ryan O’Neal who was often seen sporting the style. Since then, everyone from The Clash to Daniel Craig’s 007 (whose Harrington is, admittedly, made by Tom Ford) has showcased the silhouette’s versatility.

To this day, each Baracuta Harrington jacket is still handmade in the UK, and the design hasn’t changed a lot since 1937. The signature tartan lining remains, and it still manages to strike the perfect balance between smart and casual. But most importantly, the G9’s flipped-up collar looks unquestionably cool worn over everything from shirts and ties to crew neck T-shirts.

Baracuta G9 Harrington Jacket

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Burberry Trench Coat

Perhaps the most instantly recognisable piece of outerwear in the world, each element of Burberry’s trench coat looks as relevant today as it did more than a century ago.

The design’s form-follows-function aesthetic comes from the fact it was originally produced to keep military personnel protected against wind and rain.

Crafted from waterproof gabardine, a robust fabric invented by Thomas Burberry in 1879, the traditional silhouette features a double-breasted cut and 10 front buttons, along with wide lapels, a storm flap, belted waist and adjustable cuff straps. Yet, what many don’t know is that there’s an unresolved debate still raging on as to whether Aquascutum or Burberry developed the original version.

Whichever British heritage brand you prefer, arguably the best thing about the trench coat is its versatility. Push up the sleeves, flip the collar, throw it over a T-shirt or a suit, whatever you do, chances are it’ll still look exceptionally stylish.

The Burberry Trench Coat for Men

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Schott Perfecto Leather Biker

The Schott Perfecto motorcycle jacket has a colourful past to say the least. Banned in American schools following Marlon Brando’s iconic outing in 1953 cult biker film The Wild One, this is an item of clothing with some firepower.

Still made in the USA, the Perfecto dates back to 1937 and was named after the brand’s co-founder Irving Schott’s favourite type of cigar, which featured closed ends and a distinctive bulge at its centre.

The lancer-fronted jacket’s legacy is in no small part thanks to bands like The Ramones sporting it, but also due to Schott’s numerous innovations at the time of its release – from the Perfecto’s shorter, more contemporary cut to details like the small zip-up coin pocket on the front.

Today, you’ll find the design in a wide range of fits and finishes, from pebbled leather slim-fit to smooth coloured designs. Want our advice? Go authentic with a classic black leather jacket.

Schott Perfecto leather jacket for men

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Barbour Waxed Jacket

It’s hard to believe that the Barbour jacket was once worn solely for practical purposes. Crafted from robust waxed cotton as outerwear for the fishermen of the north east of England, and later adopted by country folk, it’s a perfect option for any outdoor pursuit, including post-work drinks in the autumn.

In recent decades the business, which remains family-owned and based in its original home of South Shields, has done well to bolster its fashion offering for those of us who wouldn’t have a clue what to do on a boat or horseback. However, the original always remains the best.

Metal hardware, a corduroy collar and stitched branding to the front left pocket look just as iconic now as they ever did, and can be continually returned to the Barbour factory for re-waxing to keep the British weather out for years to come.

Barbour Jacket


Alpha Industries MA-1 Bomber Jacket

Once known as something that surly doormen of bad clubs wore to cover their steroid-swollen arms, the MA-1 flight jacket has recently been welcomed back into the menswear fold owing to its authentic military aesthetic and unbeatable insulation.

Typified by a shiny outer shell, ribbed trims and utility pockets, examples by the likes of former US military contractor Alpha Industries reflect a time when fighter pilots were considered the most stylish guys alive (in movies, at least).

Still boasting some of that Jet Age cool, the MA-1 is ideal for pairing with a T-shirt and jeans and also lends a bit of credibility in the ‘could possibly beat you up’ stakes which – let’s be honest – is still a hit with potential significant others.

Alpha Industries MA-1

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Levi’s Trucker Jacket

A well-fitting, solidly constructed denim jacket complete with metal buttons that only gets better with age. That’s it. We could just end it there, really. But we won’t.

The Levi’s trucker, created in the early 1900s, conjures up images of hardworking Western types, but today it forms a crucial component in on-point layering.

It’s an endlessly versatile item that never goes out of style, looking just as good thrown on with a T-shirt and hoodie as it does buttoned up over a twill shirt.

If you don’t own one already, open up a new browser tab and sort yourself out, quick smart.

Levis Trucker

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Wardrobe Staples

Fred Perry Polo Shirt

Few brands have as much emotional resonance as Fred Perry. Popularised by skinheads, mods and football casuals, as well as musicians like Paul Weller, The Specials and Oasis, the brand’s tipped-collar polo is more than just a piece of clothing.

It’s hard to know exactly what has drawn so many (often disparate) types of people to the style over the years, but we’re certain the shirt’s unique fit has always played a part. Slim and flattering on a variety of body shapes, the Fred Perry polo is a more democratic alternative to the formal buttoned-up shirt.

As well as fit, the quality of the shirt’s cotton piqué fabric and its distinctive tipping has helped cement its place in the pantheon of menswear staples.

Fred Perry Tipped Polo Shirts

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Dockers Alpha Khakis

Chinos are no longer naff trousers for 1950s-era dads, and we largely have Dockers to thank for that. The San Francisco firm is to rugged twill trousers what Levi’s is to denim.

The brand’s Alpha Khaki chinos are everything you’re looking for in a pair of casual trews. Made from hardy cotton twill and coming in a timeless slim tapered cut, this model can easily weather the effects of frequent wear.

Which is good, because they can be combined with nearly everything else in your wardrobe, from a Breton stripe top to deconstructed tailoring. The true hallmark of an essential.

Dockers Alpha Khakis

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John Smedley Merino Wool Jumper

There’s a reason John Smedley was awarded a Royal Warrant. The British label’s expertly crafted merino wool knitwear is pure minimalism. No bells, no whistles, just material that is of the highest quality, having been sourced ethically and fairly from a select number of wool growers in New Zealand.

Pulling on merino’s natural moisture-wicking and temperature regulating properties, this time-honoured classic is proof that natural materials can be practical, too.

Think of it like wearing a hug. A big, flattering, crew neck hug that (providing it’s looked after) might just outlast the monarchy.

John Smedley Merino Jumper

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Turnbull And Asser Work Shirts

Turnbull & Asser isn’t exactly short of ringing endorsements, and it’s plain to see why. It’s likely that Sir Winston Churchill appreciated the bespoke shirtmaker’s mother-of-pearl buttons just as much as Heath Ledger’s Joker favoured the brand’s use of extra-long Egyptian cotton (probably).

Since 1885, the Jermyn Street stalwart has outfitted the weird and the wonderful, even earning itself a Royal Warrant along the way, and as such has always been the gold standard for the discerning man to work towards.

Whether it’s the crisp white, pink or sky blue shirts that provide the foundation of any sartorial rotation or the pleated bib front dinner suit styles, a button-up carrying this name will never fail you in a formal setting.

Turnbull And Asser Work Shirts


Levi’s 501 Jeans

Whether you pin it on the ‘normcore’ movement or a growing shift away from skinny cuts, the 501 jean is seeing a serious resurgence in popularity.

Levi’s most famous style always had the perfect not-too-loose, not-too-fitted silhouette and, like most US outfitters’ denim, they’re extremely durable, which is perhaps what won them a roll call of fans including James Dean.

Since their launch in 1873 Levi’s has periodically tweaked the fit, fabric and features of the 501 to suit the needs and preferences of the modern worker. Recently the brand released a new 501 Custom Taper (or CT) cut, recognising that a growing number of guys were getting the alteration carried out.

The result is a style that can be dressed up or down with ease, especially if you opt for a pair in a dark selvedge wash.

Levi's 501 Jeans

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G.H. Bass Weejuns

Those smart loafers you wear with your suit? They’re actually based on a style of Norwegian farming shoe, known as the Aurlandskoen (or Aurland shoe). This moccasin-like design was exported around Europe during the early 20th century and quickly became popular with visiting Americans, who took them back to the US.

In 1936, capitalising on this popularity, American shoemaker G.H. Bass launched its ‘Weejuns’ model, which took the traditional Aurland design and added a strip of leather across the saddle with a diamond cut-out – giving birth to the original penny loafer.

Still handcrafted to this day, Bass Weejuns have endured perhaps thanks to their ‘gateway’ status for those who aren’t in the habit of sporting smart shoes but still want to appear dressed-up. Versatility is a key factor, too – a pair of simple Weejuns looks just as good with rolled-up jeans as they do smart chinos or a suit.

Bass Weejuns Penny Loafers

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Converse Chuck Taylor All Star

The forerunner to Converse’s most famous sneaker model was first created 100 years ago, and the simple rubber and canvas design is still being worn by millions worldwide.

Today a new generation has thrust Chuck Taylors back into the spotlight. And who can blame them? The clean lines, fuss-free design and practical combination of rubber and canvas mean that these trainers sit well with pretty much everything and wear beautifully (that canvas upper always looks better after a little roughing up).

Not only that, starting at around £40 per pair, they’re easily replaceable and available in almost every colour and pattern under the sun.

Converse Chuck Taylor All Star Trainers

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Clarks Originals Desert Boots

The old desert boot has been through a lot since British mainstays Clarks began crafting the pioneering design in the 1950s. Remaining largely unchanged over the six decades since it was born (inspired by the crepe soles worn by off-duty officers in Cairo), it’s proved itself one of the most versatile footwear styles going.

While in 1968 you might have spotted them on Steve McQueen on the set of The Thomas Crown Affair, today you could just as easily catch a glimpse of them on currently-incarcerated dancehall legend Vybz Kartel, whose immensely catchy track ‘Clarks’ pays homage to the brand that bore the boot.

With an exceptionally comfortable construction, minimal lacing system, and smart leather and suede uppers, the Desert boot is rarely ever a bad choice to bookend your look with.

Clarks Desert Boots

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Dr. Martens 8-Eyelet Boots

Assimilated punk iconography can sometimes look a bit, well, naff (distressed patching, shoddy DIY safety pin customisation). But Dr. Martens classic 8-eye boot will always bring an instant edge to any outfit.

Known as style 1460 (after the date it launched, 1 April 1960) the shoes came about after Dr Klaus Maertens set about creating a boot with an air-cushioned sole after injuring his ankle skiing. What followed would leave a hefty imprint on everything from style to music to politics.

With a Goodyear-welted construction and clean, trend-proof design, a pair of Docs is the perfect choice for casual looks that show your historic menswear credentials. Just brace yourself for wearing them in.

Dr Martens 8-Eyelet Boots

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Gucci Horsebit Loafers

The shoe of choice for discerning men from Pitti Uomo to Garage Nation, Gucci’s horsebit-adorned loafer is intrinsically linked to London’s Garage scene of the late 1990s and early 2000s, but its decidedly classier pedigree (mid-century Florence) is also undoubted.

Steeped in Italian flair, it’s a style born to be worn sans-sock with a neatly rolled-up trouser or a pair of nattily tailored shorts once the sun’s out.

The Horsebit’s clasped metal detail on the upper is a subtle but instantly recognisable mark of distinction, while its low-profile silhouette and smooth sole mean it looks just as handsome even when outside of Florence.

Gucci Horsebit Loafers

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Ray-Ban Aviators

Like many classics, there’s a story behind these teardrop-shaped glasses. First worn by pilots during the 1930s, the style’s large lens shape provided necessary protection from glare while flying, hence the name aviators.

The style was originally developed by Bausch & Lomb, the American company responsible for launching the Ray-Ban brand in 1936, which many will know as the byword for other iconic shades such as the Clubmaster and Wayfarer.

It’s hard to pin down just why aviators became so cool. No doubt, pop cultural icons from Tom Cruise in Top Gun to Mad Men’s Don Draper have had something to do with it. Or perhaps it can be chalked up to the fact that aviators are one of those few designs that, thanks to their simplicity, not only work for almost every face shape, but also team just as well with casual get-ups as tailoring.


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