1. The Sweatshirt & Chino Trousers

As Worn By Paul Newman

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

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

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.

4. The Roll Neck & Double-Breasted Blazer

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.

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