Classic is a term that’s bandied about a lot in menswear, and despite what marketing campaigns might suggest, it takes something truly special to properly substantiate the claim.

In the search for enduring style over trends, we’ve picked out some unquestionable classics; united by brilliant design and unrivalled quality, these coveted items look as remarkable now as they’ve always done.

1. The Baracuta G9 Harrington

The Baracuta G9 Harrington Jacket

Few jackets have proved to have such wide-reaching popularity as Baracuta’s Harrington. Originally beloved by golfers at the time of its release in 1937 (chiefly for its water-resistant fabric and ‘umbrella’ back flap), the Baracuta Harrington (or G9) went on to be adopted by several subcultures from skinheads to scooterboys, as well as celebrities lauded for their style including Frank Sinatra and Steve McQueen (above).

To this day, each Baracuta Harrington jacket is still handmade in the UK. Strangely enough, the name comes from a character in 1960s American soap opera Peyton Place; Rodney Harrington, played by Ryan O’Neal, was often seen sporting the style, leading to the G9 being dubbed the ‘Harrington’. Since then, everyone from The Clash to Daniel Craig’s 007 (whose Harrington is, admittedly, made by Tom Ford) have showcased the silhouette’s versatility.

The design hasn’t changed a lot since 1937 – the signature tartan lining remains and it still manages to strike that 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 tees.

Baracuta G9 Harrington Jacket

Baracuta G9 Original - NavyBaracuta G9 Original - NaturalBaracuta G9 Original - Oil GreenBaracuta G9 Original - Off Black

2. The Aquascutum/Burberry Trench Coat

The Burberry Trench Coat

Maybe the most famous piece of outerwear in the world, each element of Thomas Burberry’s trench coat still looks relevant today thanks to the design’s form-follows-function aesthetic, rooted in its military origins.

Typically crafted from waterproof cotton gabardine drill or poplin, the traditional silhouette features a double-breasted cut and ten 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 whether Aquascutum or Burberry invented the original version.

Whichever brand you prefer, arguably the best thing about the trench is its versatility and the degree to which you can customise it: push up the sleeves, flip the collar, belt it at the front or back, throw it over a T-shirt or a suit and it’ll still look exceptionally stylish.

Baracuta G9 Harrington Jacket

Aquascutum Corby Double Breasted RaincoatBURBERRY COTTON-GABARDINE TRENCH COAT

3. The Schott Perfecto Leather Biker

The Schott Perfecto Leather Biker Jacket

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

Still made in the USA, the Perfecto dates back to 1937 and was named after 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 – from the Perfecto’s shorter, more contemporary length to water-resistant leather options and details like the ingenious coin pocket.

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

Schott Perfecto Leather Biker Jacket

4. G.H. Bass Weejuns Penny Loafers

G.H. Bass Weejuns Penny Loafers

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 in 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 bootmaker 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 – and so the original penny loafer was born.

Still handcrafted to this day, they’ve 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

Bass Weejuns Larson Penny Loafers in BlackBass Weejuns Larson Classic Loafers in CognacBass Weejuns Larson Penny Loafers in BurgundyBass Weejuns Larson Penny Loafers in Brown

5. Converse Chuck Taylor All-Stars

 Converse Chuck Taylor All-Stars Trainers

Converse’s most famous sneaker model was first created 98 years ago – and the simple rubber and canvas design is still being worn by millions worldwide.

It’s no wonder that a new generation has thrust Chuck Taylors back into the spotlight; 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, at around £40-60 per pair, they’re easily replaceable and available in almost every colour and pattern under the sun.

Converse Chuck Taylor All-Stars Trainers


6. Ray-Ban Aviators

Ray-Ban Aviator Sunglasses

Like many classics, there’s a story behind the name of these teardrop-shaped glasses. First worn by pilots in 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 American company Bausch & Lomb, which was responsible for launching the Ray-Ban brand of sunglasses in 1936. Although Ray-Ban has since been sold to the Italian Luxottica Group, its iconic aviator style – along with other timeless frames such as the wayfarer and clubmaster – has endured thanks to a commitment to high quality construction techniques, innovation (check out the brand’s foldable aviators) and affordable price points (classic styles sit around the £120 mark).

It’s hard to pin down just why this sunglass style became so cool. Doubtless, pop cultural icons from Tom Cruise in Top Gun to Mad Men’s Don Draper have had something to do with it, but then again, aviators are one of those few designs that, thanks to their simplicity, not only work for almost every face shape, but team just as well with casual getups as tailoring.

Ray-Ban Aviator Sunglasses

Ray-Ban Foldable Aviator SunglassesRay-Ban Aviator Sunglasses 0RB3422QRay-Ban Aviator Polarised Sunglasses 0RB3025Ray-Ban Aviator Sunglasses 0RB3025

7. Levi’s 501s

Levi's 501s CT Jeans

Whether you pin it on the ‘normcore’ movement or a growing shift away from skinny silhouettes, the 501 is seeing a serious resurgence in popularity. Levi’s most famous jean style always had the perfect not-too-loose, not-too-fitted silhouette; and like all of the American outfitters’ denim, they’re dependably durable, whether you’re planning some heavy-duty work or a particularly hard night out on the town.

Launched in 1873, Levi’s has periodically tweaked the fit, fabric and features of the 501 over time to suit the needs and preferences of the modern worker. Although these changes were often subtle and only apparent to the discerning eye, it has played a huge part in the style’s enduring success and popularity over generations.

And the 501 continues to evolve to this day. Recently the brand has released a new 501 Custom Taper (or CT) cut, because “tapering the leg is the most requested alteration,” according to Levi’s SVP of Global Design, Jonathan Cheung. 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.

A lot of vintage shops also customise 501s to give them a slimmer, more modern fit – so it’s well worth exploring the second-hand market, too.

Levi's 501 Jeans


8. The Fred Perry Tipped Polo Shirt

The Fred Perry Tipped 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’s drawn so many (often disparate) types of people to the style, but 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 – “kind of like a hip semaphore,” according to Fred Perry fan and The Specials’ bassist Horace Panter – has helped cement its place in the pantheon of menswear staples.

Fred Perry Tipped Polo Shirts

Twin Tipped Fred Perry ShirtTwin Tipped Fred Perry ShirtTwin Tipped Fred Perry ShirtTwin Tipped Fred Perry Shirt

9. The Louis Vuitton Keepall

The Louis Vuitton Keepall Holdall Bag

What’s really special about this much-praised bag is its proportion. Not too small, not too bulky, whatever size you choose, it’ll always have space for a weekend’s worth of clothes, but isn’t so big as to be obtrusive around town either.

Since the keepall’s release in 1930, Louis Vuitton has expanded into everything from monogrammed travelling wardrobes to transportable furniture, but this timeless bag has retained its streamlined design, surprisingly spacious interior and the shape that has inspired thousands of holdalls ever since.

The pinnacle of luxury luggage, if you’ve got the budget, the Keepall makes a solid investment and will last you a lifetime if cared for properly.

Louis Vuitton Keepall Bag

Louis Vuitton Keepall Bag

Louis Vuitton Keepall Bag

10. The Rolex Submariner

The Rolex Submariner Watch

When it launched in 1953, the Submariner must have seemed revolutionary; the first timepiece to be water resistant to 100 metres, it set the standard for divers’ watches during what many consider to be the pioneering era for scuba diving.

According to Rolex, the Submariner is a “divers’ watch that you can wear with a tuxedo”. Enter James Bond – perhaps one of the only men whose daily activities span from infiltrating underwater bases to donning a tux for a formal event afterwards – whose early outings on the silver screen (particularly Sean Connery’s tenure as 007) served as one of the core drivers of the model’s popularity.

Arguably one of Rolex’s best-known watches, the Submariner is famed for its incredibly tough steel case, a super-comfortable strap and, of course, reliability and precision down to depths of 300 metres, all combined with timeless good looks that are a world away from the cheaper-looking, rubbery styles that have muddied the waters since.

Rolex Submariner Watches


Final Word

There’s something truly special about garments that have been worn for decades and still look good today. This list isn’t definitive, but serves as an introduction to some of the undisputed style legends to look out for.

Which items of clothing or accessories do you class as iconic?

Let us know your recommendations in the comments section.