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Navigating the shifting seas of fashion can be tricky, so modern men need a core of go-to outfits in the wardrobe that they can always rely on to have them looking their best.

Thankfully, these looks are already in existence, in fact they have been for years.

Sported by some of history’s coolest men, they are stylish, easy to wear and above all, never get tired. So stock up on one (or all) of the following, and invest in a little sartorial insurance.

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1 | The Navy Suit

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Every man looks good in navy. Whether it’s a seersucker blazer, a cotton jersey or a Gabardine mac, it’s a shade which transcends both time and trend. The pinnacle? The navy suit – a timeless, understated and infinitely cool old friend that will always have you looking your best, as Esquire's October cover star Michael Caine readily illustrates. Jeremy Hackett describes it as ‘the men’s version of the little black dress’, and he’s absolutely right, although twinning it with five inch heels might be a bit much.

Hackett Mayfair Herringbone Suit, £600. hackett.com 
 

2 | White T-shirt, Blue Jeans

Nailing such a basic look might seem easy, but you need to have the right ingredients. Invest in a white T-shirt cut from good cotton - you’ll soon realise its merits can’t be understated. And opt for slim (but not too slim) blue jeans devoid of pre-imposed rips and streaks. If they’re good, they’ll wear-in all by themselves. For the definitive tip on getting it right, see Marlon Brando in Streetcar Named Desire. To channel the full look you’ll need to hit the gym. Hard. But we’ll leave that to you.

Sunspel White T-shirt, £55. sunspel.com.  Nudie Thin Finn Jeans, £155. nudiejeans.com.


3 | The Trench Coat

A guaranteed way to smarten up (or perhaps obscure) any slightly iffy look, the origins of the trench coat are in dispute, but its fundamental virtues are not. Take one look at Humphrey Bogart in the closing scene of Casablanca and you’ll understand; a collar to frame ones face, a belt to cinch in a potentially wayward midriff and a length that elongates the silhouette. What’s more, the trench coat can be employed to cover up all manor of sins, making even the shabbiest of gents look up to scratch.

Burberry Kensington Mid-Length Trench Coat, £1095. burberry.com.
 

4 | Harrington Jacket, Chinos and White Trainers

 
Stylish men don’t clock off at weekends. They don’t drop the act and climb into a onesie come 6pm on a Friday night. They consider their look wherever, and whenever. With that in mind, the combo of a Harrington jacket, pale chinos and white trainers has to be the surest way to look good in any off-duty scenario. For inspiration in this - and pretty much any other - situation, look to Steve McQueen. An obvious role model, but for very good reason.
 
Baracuta G4 Original Harrington jacket, £279. baracuta.com. Farah Cotton Twill Trousers, £60. farah.co.uk. Lyle & Scott Halket Trainers, £47. lyleandscott.com.


5 | The Roll Neck Sweater And Pea Coat

It’s no secret that a good roll neck sweater goes a long way, but there’s a knack to wearing one, and it can all go very wrong very easily. Here Dylan, (complete with shades) gets it right with his black rollneck nestled beneath the popped-collar of a wool pea coat (blacker still). Plus, a motorbike never hurt anyone's image. 

Topman Rollneck Jumper, £24. topman.com. H&M Reefer Jacket, £59.99. hm.com.


Anything we've missed?


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