In a way this has been a long time coming, in all of my articles so far I’ve mentioned the words “timeless style” without explaining it in any detail. So over the course of this article I would like to explore the notion of timeless style, take a look at the men who embody it, debate whether it’s better to be stylish or trendy and just what the difference is. I hope you enjoy it.

What is timeless style?

Timeless style is easy to define yet hard to explain; simply it’s a sense of style or a way of dressing that will never go out of date or become unfashionable. In my opinion though timeless style is so much more than this. Like many things in menswear it is elusive and seemingly unattainable – men don’t have the same amount of choice in our wardrobe as women do, so we compensate with rules and what seems to be unreachable aspiration. Timeless style is generally only accessible when wearing certain clothes which embody the whole persona (more on this later).

So how exactly does a piece of clothing become timeless? After all, every piece of clothing at some point in its life has been part of some kind of trend – such is the cyclical nature of the fashion industry. In answer to this question, I personally think that for an item of clothing to become timeless it must have some kind of impact on popular culture – whether that be someone cool wearing it in a film, an artist painting it or a singer writing a song about it. If someone who has a lot of public support (and approval) wears a particular piece whilst doing something iconic then the item is well on its way to being cemented into the wardrobes of the world’s most stylish men. Of course this has to happen on more than one occasion for it to truly become timeless and last generations.

I’d like to craft a simple story to explain what I mean: An item of clothing is in fashion, so people of taste and influence begin to wear it, inevitably these items of clothing begin to appear in popular culture, the popular culture itself (be it a film, photo, concert, person etc.) is judged to be timeless, and in a chain reaction so does the item of clothing associated with it. To sum it up in an even shorter way: Fashion gives way to style.

The Men Who Embody It

Now, throughout the last 60-ish years many different men have embodied this sense of timeless style. I’m going to list some of them and then talk about the common characteristics that they all seem to share: Steve McQueen, Paul Newman, Marlon Brando, James Dean, Marvin Gaye, Otis Redding, Sammy Davis Junior, Miles Davis, Jonny Depp, Cary Grant, Humphrey Bogart, Brad Pitt, George Clooney, Tom Ford, Jamie Foxx, Aaron Johnson, Douglas Booth and Alex Turner.

Now this is just a very brief and varied list of some of the men I believe have a sense of timeless style. Obviously they don’t dress in a timeless way every single day, but that is because developing a timeless style requires more than just considering the clothes you wear. All these men seem to share a number of personal characteristics; the first – and KEY – being confidence. Most of them have to be confident because their jobs push them into the public eye, but if you take time to watch them (their actions, how they speak, their mannerisms) you will notice they have a sense of true inner confidence which just oozes out of them. With this confidence comes an innate sense of style and fashion – knowledge of what always looks good on them and in what situation. These men are all undeniably “cool” (see my earlier article). Cool seems to go hand in hand with timeless style; cool people make an item timeless and timeless items make people “look” even cooler.

As a visual example, take a look below at some of the icons mentioned. You could take each and every one of these out of the generation they lived in and put them in another and they would look just as good and still have that aura about them. Whether you took Marvin Gaye in his denim shirts and workerwear from the 80s, Sammy Davis Junior sharply dressed in his suit from the 60s or James Dean in his trademark leather jacket or trench from the 50s – each and everyone of them would still look just as great today if they dressed exactly the same way. They had an innate sense of style which transcended generations and every cyclical trend we have seen in between. The same rules would apply if you took Clooney, James Franco or Jamie Foxx back 3 generations.

Timeless Men's Style Icons

This is why many fashionable males who are prominent today may not have the longevity of some of those 50s and 60s icons mentioned above. As an extreme example, David Beckham is indisputably one of the most fashionable males on the planet. However, I think that he is constantly reinventing his look and moving with the times. He knows what looks great and he knows all the current and future trends – a true fashion leader rather than follower. However, for the everyday male, to follow this approach would be very costly and require much more time and effort researching every new trend and type of item that comes out each and every season. His personal style is not timeless, it will date but he will reinvent himself before it does. So this leads us on to the age old debate of trending versus developing a personal style…

Trending Vs Style

This is a very complicated matter and has already been covered in an excellent article on this site, but it’s a debate that will go on for a long time. It’s a true chicken and egg problem isn’t it? I think it’s almost universally accepted in the fashion world that style trumps trends and fashion (“fashion is temporary, style is eternal” – Yves Saint Lauren) but without these trends, nothing would ever have the chance to be classed as stylish!

To give you my take on the debate, I think they are both equal. I see trends and fashion as a form of exploration, people discovering what looks good on them and why, whereas style is all the things that have passed the test. I think that people should spend their youth exploring trends and fashions – they should enjoy the thrill of exploration and all the exciting things that go with it, but as a gentleman matures he should learn from these experiences and begin to build a true understanding of style and elegance. When the time comes for him to hang up his “boots”, he can turn to his wardrobe knowing he has a collection of clothing and a look unique to him that will last forever; something he has spent years trying to understand, a collection he knows will always make him look good – no matter what trends come and go.

That’s style in a nutshell; lessons learned on a long, exciting and somewhat dangerous journey. Never mind what I think though, this is a debate that I have no doubt will continue for a long time, so what do you think? Is there a difference between style and fashion/trends? Is one more important than the other? Which one do you prefer and why? I hope these questions provoke some constructive and exciting debate in the comments below.

The Clothes

I’ve spoke at length about the ideas behind timeless style, the men who embody it and the difference between style and fashion, but now I think it’s time to talk about some pieces that ARE timeless. Pieces I think everyone should own and items I know will look fantastic on you.

Now a quick note: I have provided a mix of items for all budgets in this article, but if I were you I would invest as much as you can possibly afford in timeless pieces. This isn’t because I believe the high street can’t provide true timeless pieces, it’s because I want these items to last you a lifetime, I want you to be able to treasure them forever, and unfortunately a heftier price tag means a better quality garment.

Leather Jackets

The leather jacket has been a symbol of ultimate cool now for years. James Dean in rebel without a cause, John Travolta in Grease, Arnold Schwarzenegger in all of the Terminator films and numerous other examples in popular culture have cemented the leather jacket as a style staple. It can be worn with just about anything casual, and most importantly it’s understated (unless you buy a bright yellow one – don’t do this) which means it fits in with the whole not really trying vibe all men strive for.

Icons in Leather Jackets

  • ASOS Leather Aviator Jacket
  • Diesel Luppyro Leather Pilot Jacket
  • Viper Jacket
  • Razor Leather Biker
  • lot 78 Collarless leather jacket
  • JOFAMA Albert Chocolate Brown Leather Bomber Jacket
  • Gucci Leather Bomber Jacket
  • Ralph Lauren Black Label Leather Biker Jacket
The Trench Coat

A spring essential but it can be worn all year round, the trench coat has never gone out of fashion and can be seen on men all around the word. From the black and white films of the 40s to the present day, the trench coat remains a must have piece of clothing. I’d recommend the classic khaki colour or a black/navy version if you want something a bit sharper. Use it over a suit, or a simple jeans and polo shirt combination for a more dressed down look. Wear it closed and tied to make a formal statement or open with the belt tied around the back for a more casual look. Bottom line: Invest in a good trench coat; it will serve you well year after year.

Icons in Trench Coats

  • Camel Belted 3/4 Trench Coat
  • Burberry Prorsum Double-Breasted Trench Coat
  • Walton Trench Coat
  • Burberry Taupe Classic Double Breasted Trench Coat
  • Amend Mac
  • Navy Belted 3/4 Trench Coat
  • Burberry Black Packable Trench Coat
  • burberry prorsum<br /> Cotton trench coat
The Blazer

What was once reserved only for drinks at the golf course or the yacht club is now a versatile piece that can be worn for just about any occasion. The blazer has the unique ability to both dress up and dress down different outfits. Wear it with a v-neck t-shirt and a pair of jeans and you instantly look smarter, pair it with some trousers and you suddenly look more causal than the people in full suits. I’d recommend a navy blue one for spring/summer and a grey one or autumn/winter, although a black blazer can be worn at any time and is great for party season.

Icons in the classic blazer

  • G Star Midnight Suit Jacket
  • River Island Single Button Suit Jacket
  • Alfred Dunhill Unlined Wool Blazer
  • Gucci Single-Breasted Peak Lapel Blazer
  • Alexander McQueen Double-Breasted Cashmere Blazer
  • Yale Blazer
  • Our Legacy 100s Single Breasted Suit Blazer
The Suit

Quintessentially male, the suit is every males formal uniform of choice. Always smart, the suit can be worn as easily to work as it can to a cocktail party. The suit comes in different styles and colours: single breasted, double breasted, three piece, one button, two button, peak lapels, shawl collar, black, white, grey, navy or even brighter colours in summer. Pick your poison as the list is a long one. If you want something that is truly timeless, then stick to a two button mid to dark grey suit – it will work at any situation you throw at it.

Icons in suits

  • ASOS Slim Fit Navy Suit
  • ASOS Sharkskin Pindot Suit
  • Ralph Lauren Black Label Anthony Pinstripe Wool Suit
  • Gucci Two Button Lightweight Suit
  • zegna sartorial Micro-stripe wool suit
Polo Shirt

The polo shirt is the love child of the shirt and the t-shirt, treading the line between smart and casual. I love polo shirts, they are just so versatile, and let’s be honest, pretty damn cool – think Sinatra on the golf course. The polo shirt works well in pretty much any colour (you can be as bold as your taste allows), although I’d avoid patterns and focus on block colours. Pair with an understated pair of jeans or chinos in a complementary colour.

Icons in Polo Shirts

  • FRED PERRY LAUREL M3 Black Polo Shirt
  • Ben Sherman Tipped Romford Polo Shirt
  • Fred Perry Pin Dot Printed Polo
  • ralph lauren Slim polo T-shirt
  • LYLE & SCOTT Lyle & Scott KC648V22 Yellow Polo Shirt
  • Burberry Brit Pique Polo Shirt
  • Polo Ralph Lauren Custom Fit Pique Polo Shirt
Slim Jeans

Jeans are an obvious choice, so much so that I could safely say that everyone reading this owns at least one pair of jeans, probably many more if you are like me. But there’s a reason they are so popular; they come in a variety of different styles and washes/colours, they are comfortable and most importantly you can wear them with anything. Seeing as you probably own numerous pairs of jeans, I’d suggest investing in just one pair of high end dark indigo jeans in a slim or straight cut. That way you know that long after you’ve replaced all the other trend pairs, you’ll still have that one pair that will work in any outfit, at any time in your life.

Icons in Jeans

  • Raw Blue Slim Jeans
  • McQ by Alexander McQueen Straight Rinse Jeans
  • Evisu Rinse Wash 2008 Straight Jeans
  • ARMANI JEANS J21 Straight Leg Jeans
  • Yves Saint Laurent Skinny Fit Denim Jeans
  • acne Max soft raw jeans
  • NUDIE Grim Tim Dry Dirty Organic Jeans
  • A.P.C. Petite Standard Slim Selvedge Jeans

So there we have it, some pieces that I consider to be timeless. Now obviously that’s not everything, the list is a long one and people have strong personal opinions on what works for them and what items they consider to be timeless. I hope you enjoyed it and it gave you the inspiration to start building a timeless wardrobe. Let me know what you consider timeless in the comments section and let’s see if we can’t get a good old man argument going.

“Time is free, but it’s priceless. You can’t own it, but you can use it. You can’t keep it, but you can spend it. Once you’ve lost it you can never get it back.” – Harvey Mackay