It’s a widely accepted truth that some wardrobe classics never date; a black leather biker jacket looks as slick today as it did on Brando in The Wild One, and no item of clothing will ever top a white button-down Oxford shirt’s versatility.
But if these are the staple pieces you can’t be caught without, then what are the looks that persist in menswear as trends come and go? Below you’ll find nine timeless sartorial combinations that may be paid less lip service than their individual components, but which each have an appeal that’s much more than the sum of their parts.
Simple, stylish and easy to wear, these iconic looks (worn here by similarly iconic men) never get old.
The Leather Biker & White T-Shirt
As Worn By Marlon Brando
Why It Works
You know something is a wardrobe classic when even those who claim to have zero interest in men’s style could comfortably reel them off. What’s even greater than one menswear classic is three, thrown together in a sartorial holy trinity.
Marlon Brando understood this, and not only did he get it, he practised what he preached. His now legendary pairing of a black leather biker jacket, a white crew-neck T-shirt and selvedge denim jeans has become the unofficial uniform of cool for multiple generations. In the 1970s it got a bit hippy, in the 1980s it got skinny, in the 1990s it got grungy and in the 2000s a bit indie rocker.
You don’t need much advice on pulling this look off other than to stick to the tried-and-true formula for everyone that went before you: keep it simple. And lose the motorcycle cap.
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The Shearling Jacket & Grey Jumper
As Worn By Robert Redford
Why It Works
If you’re going to invest in a quality one (and we strongly recommend that you do), a shearling jacket will cause your bank account considerable damage. Fear not though, since it was first popularised this shaggy staple has never really gone away, so that initial big hit will pay off eventually.
Styling wise, as long as you give the Del Boy flat cap and chain a miss you’ll struggle to make a mess of wearing one, too. If you’re looking for a cast-iron guarantee that you’ll do your shearling jacket justice, Robert Redford is the only man you need to consult. Since he casually donned a shearling jacket with a grey jumper and shirt in 1969’s Downhill Racer, we’re at a loss to think of a time when one has been worn even half as well. That’s an unbroken record of nearly 50 years; a cast-iron look.
The beauty of this pairing is that you don’t need to worry too much about what’s going on with your bottom half; this combo works well with jeans, tailored trousers and chinos. The only exception is tan or sand chinos, which will make you look like a football commentator from the 1980s. And not in a good way.
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The Sweatshirt & Chino Trousers
As Worn By Paul Newman
Why It Works
Since leaving the playing field and taking up residence in the wardrobes of stylish men everywhere, the sweatshirt’s enduring success (it has been worn by practically every style tribe imaginable) has always been in its simplicity.
Few men understood this as well as Paul Newman, who regularly paired his sweatshirts with another preppy classic: chino trousers.
What is it about this combination that works so well? It’s essentially a case of ‘opposites attract’. Chino trousers – while less formal than tailored trousers – have a vague air of formality. Conversely, the sweatshirt lends its wearer an unfussy, relaxed edge.
Together, these unlikely bedfellows make a pairing that lands right in that sweet spot for smart-casual dress codes, providing you with a means to look effortlessly stylish while off-duty.
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The White T-Shirt & White Jeans
As Worn By Steve McQueen
Why It Works
Is there a combination that’s easier to throw on than a white T-shirt and pair of light jeans? Yes, there are those tricky nuances of light and shade to master with this coupling, but the rewards to be reaped are worth it. It’s a fast track to summer-ready style in two pared-back steps.
Though the idea of a wearing a crew neck T-shirt with jeans in the same shade might seem simple enough, donning the classic look can stump even the most savvy of dressers. Firstly, there’s the issue of choosing a skin tone-appropriate shade of white (darker cream and stone work best for those with paler complexions, by the way), followed by the small matter of how to match shades.
Take your cue from a man who knew how to wear almost anything well: Steve McQueen. Typically opting for jeans a shade or two darker than his white tee, McQueen mastered a look that continues to feel fresh year after year.
If, however, your local temperature doesn’t match LA’s, then switching out a short-sleeved T-shirt for long-sleeved style works equally well, as does throwing a bomber or cardigan over the top in a contrasting hue.
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The Casual Shirt & Tailored Trousers
As Worn By Alain Delon
Why It Works
The matter of dressing off-duty without compromising on sharp style has long troubled men used to restrictive yet helpfully instructive work dress codes. What’s the best way to achieve a look that feels both relaxed and refined?
In a casual shirt Alain Delon found the answer, teaming it with tailored trousers to nail an approach to casual style that managed to be dressed down and up at the same time. So effective was the pairing, it became synonymous with Delon both on and off the screen.
As one of menswear’s most pared-back yet put-together looks, this combination is timeless because it’s a blank canvas that you can experiment with. With a few canny styling tricks your casual shirt and tailored trousers base can be transformed for a whole host of different purposes.
To add a preppy spin, all that’s needed is a shawl collar cardigan or luxe varsity jacket, while unbuttoning a couple of buttons on the shirt and rolling up the trousers’ hems offers a more relaxed take on the pairing.
Stock up on both in a few colourways so that there’s always an easy, stylish outfit waiting in your wardrobe.
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The Breton Top & Tailored Blazer
As Worn By James Dean
Why It Works
Largely unchanged since its introduction into the uniform of the French navy in the mid-nineteenth century, the Breton top has become something of a wardrobe stalwart, giving you shore leave to rock a pattern without needing to think too hard.
Although the design can be worn stylishly many different ways, the garment is at its classic best when layered beneath a tailored navy blazer. This pairing is stylish to the extent that it now forms the core of modern Riviera style. For a fuller (and more formal) look, try teaming a Breton tee with a full navy suit for a suave high-low combination.
And if you needed any more convincing that a Breton top and navy blazer is one of menswear’s most timeless combinations, you only need look back on the wardrobe of James Dean. His effortless adoption of the pairing demonstrates why this outfit made just as much sartorial sense half a century ago as it does today.
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The Roll Neck & Double-Breasted Blazer
As Worn By Michael Caine
Why It Works
Despite its tendency to divide opinion, the roll neck has long been worn by menswear’s sharpest dressers during the colder months.
And few men have embraced the roll neck’s merits so enthusiastically (or successfully) as Sir Michael Caine. Whether on a movie set or the streets of London, the actor’s signature pairing set an example which still feels relevant for the modern man.
As suave as the roll neck appears (especially if woven from cashmere or wool), at its heart it’s an entirely practical design. It will keep you warm and not un-cool, either.
Add to this the double-breasted blazer’s knack for cutting a sharp and powerful silhouette and you’ve got a sophisticated way to wear tailoring and knitwear at the same time. What’s more, this look is versatile enough to be worn on a night out, to travel in or to the office (dress code permitting) – a true all-rounder.
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The Field Jacket & Button-Down Shirt
As Worn By Montgomery Clift
Why It Works
Military-inspired menswear pieces usually fall into one of two categories: costume or cool. While the whole brass buttons and epaulettes thing can quickly go from statement to stale, more incognito designs enjoy perennial popularity. Take the field jacket – rarely used in its actual intended capacity but regularly adopted by some style subset or other.
For us, the textbook way to wear the design well comes courtesy of Montgomery Clift who effortlessly took the field jacket from battle-ready garb to unassuming menswear hit with seemingly no effort whatsoever. That’s because he was rarely seen in one not layered over a button-down shirt. Simple, effective.
While Monty’s signature wide-leg trousers may not be to every man’s taste, a slim pair of chinos or jeans will do similar justice to this time-tested combo.
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Camel Tailoring & Light Blue Shirt
As Worn By Bryan Ferry
Why It Works
There’s probably some scientific reason why camel and pale blue work so well together, but all you really need to know is that this pairing is a style no-brainer – especially when it comes to tailoring.
We’ll concede that a camel suit and pale blue shirt might seem a bit University Challenge on first reading, but boffin vibes are easily averted when a little bit of nuance is applied. Take a leaf out of Bryan Ferry’s book and offset mid-camel with pale blue but go slim with your suit’s cut to avoid looking older and wiser – and a little less stylish – than you actually are.
If a full camel suit is a bit too #menswear for your liking, then a pair of black or stone jeans will work just as well in lieu of suit trousers for a sharp separates combination.
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