5 Menswear Looks That Are Always In Style


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 five 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 mere sum of their parts.

Simple, stylish and easy to wear, these iconic looks (worn here by five similarly iconic men) never get old.

1. The Sweatshirt & Chino Trousers

As Worn By Paul Newman

Paul Newman Sweatshirt & Chinos Outfit

Why It Works

Since departing playing fields for the wardrobes of stylish men everywhere, the sweatshirt’s enduring success (it has been worn by practically every style tribe imaginable in one form or another) has always been in its simplicity.

Few men understood this as completely 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 an air of vague formality. Conversely, the sweatshirt lends its wearer an unfussy, relaxed edge.

Together, these unlikely bedfellows make a pairing that lands right in that smart-casual sweet spot, providing men with a means to look effortlessly stylish while off-duty.

2. The White T-Shirt & White Jeans

As Worn By Steve McQueen

Steve McQueen Wearing A White T-Shirt & Jeans Combination

Why It Works

Is there a more time-honoured (and easy to throw on) combination than a white T-shirt and pair of white 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 this classic look can stump even the most savvy of dressers. Firstly, there’s the issue of choosing a skin tone-appropriate shade of white (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 T-shirt, McQueen mastered a look which continues to feel fresh year after year.

If, however, your local temperature doesn’t match LA’s, then switching out a short-sleeved tee for long-sleeved style works equally well, as does throwing a bomber or cardigan over the top in a contrasting hue.

3. The Breton Top & Tailored Blazer

As Worn By James Dean

James Dean In A Breton Top And Blazer Combination

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, enabling its wearer to try their hand at 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 to sharpen things up. So stylish is this pairing that it’s come to form the core of modern Riviera style.

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 over half a century ago as it does today.

Tip: Try teaming a Breton tee with a full navy suit for a high-low combination that’s hard to beat.

4. The Roll Neck & Double-Breasted Blazer

As Worn By Michael Caine

Michael Caine in A Roll Neck and Double-Breasted Blazer Combination

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. Little surprise, then, that this knit hero is drawn upon by discerning dressers as soon as temperatures start to take a tumble.

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.

The Oxford Shirt & Tailored Trousers

As Worn By Alain Delon

Alain Delon in an Oxford Shirt & Tailored Trousers Combination

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 the classic Oxford shirt (teamed with tailored trousers) Alain Delon found the answer, and in the process he nailed an approach to casual style that managed to be both 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’s timelessness is directly related to its ability to be a blank canvas for its wearer to experiment with. With a few canny styling tricks your base of an Oxford shirt and tailored trousers 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 the Oxford shirt’s collar and rolling up the tailored trousers’ hems gives rise to a more relaxed take on the pairing.

Whichever way they’re worn together, there’s no doubt this duo has become a go-to for generations of men.

Final Word

Yes, most menswear items may have been nipped, tucked, reinvented and revived many times, but the fact remains that certain combinations transcend seasons, years and generations. Executed well, these looks are the key to consistently stellar style.

What are the looks that you rely on no matter the season? Which pairings would you add to our list?

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