Our series enlists expert help to pinpoint every new piece your budget should buy. This week, what to buy if you’ve got cash to burn.

1 Shearling Leather Jacket

When the sky’s the limit, look to it for your inspiration. This season’s key piece, the shearling flight jacket, was invented for pilots in uncovered cockpits. “It’s perfect for keeping the warmth in,” says Tom Courcey, editor at The Idle Man.

But trending doesn’t mean trend – as with anything military, you can wear yours every season until it falls apart. Especially if you go for a staple colour such as black or brown, which will match most things in your wardrobe. Good for morning decision-making – and the cost-per-wear ratio.

Schott Bombardier Shearling Jacket Brown, available at The Idle Man, priced £594.90.

Schott Bombardier Shearling Jacket Brown

1 Luxury Holdall

We’re a generation of multi-taskers: flitting between work meetings, lunchtime gym sessions and weekends away. Three things that command an all-round luggage performer.

“A great travel bag is an essential as it’ll get used on the daily,” says Courcey. “And once you’ve found a durable style that matches your own tastes, you’ll be thankful you forked a few extra quid on extra durability. Look for something that can fit a gym kit and enough for a couple of nights away.”

Louis Vuitton Keepall Bandouliére 45, available at Louis Vuitton, priced £1,130.

Louis Vuitton Keepall Bandouliére 45

1 Pair Of Black Leather Loafers

It’s your feet that traipse the ground everyday, so don’t skimp on what covers them. “Leather footwear is a staple as they’ll outlast trainers on both a trend and practical front,” says Courcey. “Loafers in particular are extra versatile, as not only do they look sharp with dark jeans, they perfectly anchor a suit too.”

G.H. Bass & Co. Weejuns Classic Penny Loafer Black, available at The Idle Man, priced £124.90.

G.H Bass & Co. Weejuns Classic Penny Loafer Black

1 Trench Coat

When your great grandad rocked the same coat as you, there’s a strong probability that you’re onto a winner. And there’s no piece more timeless than the trench coat.

“A decent trench can be worn with everything and anything,” says Courcey. “Nobody does prestige like Burberry. The material is 100 per cent cotton with a calf leather trim, with genuine buffalo horn buttons and full lining for extra protection.” Free monogramming means that even a ubiquitous piece can be made one-of-a-kind.

Burberry Westminster Long Heritage Coat, available at Burberry, priced £1,395.

Burberry Westminster Long Heritage Coat

1 Waxed Jacket

“Despite the rural association, waxed jackets are increasingly becoming an urban essential due to their hard-wearing fabric and sheer versatility,” says Courcey. “Team with a white shirt and black trousers for an inner city smart-casual vibe, or with stonewash jeans and a white tee for the off-duty.”

Style notes aside, there is an element of maintenance involved. Waxed jackets usually need re-coating once a year to enforce the waterproof fabric. Barbour’s Thornproof Wax (£9.95, johnlewis.com) does the job, or you can let the brand’s in-house experts give it some TLC.

Barbour Ashby Waxed Field Jacket Black, available at The Idle Man, priced £198.90.

Barbour Ashby Waxed Field Jacket Black

3 Cotton Shirts in Neutral Colours

Fit, wearability and quality are three things you should look for. A flattering shape (but not skin-tight) will sit above or beneath a multitude of pieces and still allow your skin to breathe. A neutral colour palette will ensure you get plenty of wear, while a high-grade cotton construction means your shirt will survive dozens of laundry rounds.

“I go to Ralph Lauren for all my shirts,” says Courcey. “In addition to the usual cotton Oxfords, experiment with chambray fabrics to give your outfits added depth and texture.”

Ralph Lauren Button-Down Oxford Shirts, available at Mr Porter, priced £85 to £110.

Ralph Lauren Button-Down Oxford Shirts

1 Bomber Jacket

The military essential has refused to shift for the past few seasons, which raises suspicions that the bomber jacket could well be tomorrow’s menswear classic. And that deserves investment.

“These days, a wardrobe arsenal is incomplete without a bomber,” says Courcey. “They’re a great transitional piece to throw on in tricky summer-to-autumn months, and often flatter your upper body with a design that boasts roomier biceps and wider shoulders.” And as for colour? “Black is a safe option, but navy or green can be utilised for a more a tonal look.”

Acne Studios Selo Shell Bomber Jacket, available at Matches Fashion, priced £410.

Acne Studios Selo Shell Bomber Jacket

1 Breton Stripe Jumper

A French law passed in 1858 dictated that the Breton was to be the official uniform of French sailors, as the stripes made it easier to spot men who’d gone overboard. It’s since become a staple back on dry land.

“The cliché of ‘stripes always being in’ actually has value,” says Courcey. “Every autumn-winter season, there are countless runway iterations. Which means pieces like this Saint Laurent sweater will likely get wear for the rest of your life.”

Saint Laurent Slim-Fit Striped Cashmere Sweater, available at Mr Porter, priced £605.

Saint Laurent Slim-Fit Striped Cashmere Sweater

1 Pair of Chelsea Boots

Trainers with your civvies and brogues with your tailoring. But what is the midpoint? “Chelsea boots have all the formality of shoes, but are less stuffy,” says Courcey. “They sit just as well with denims as they do with tailored trousers. Plus, hard-wearing boots will combat December slush on the commute, providing you maintain them.”

John Lobb Lawry Polished-Leather Chelsea Boots, available at Mr Porter, priced £1,120.

John Lobb Lawry Polished-Leather Chelsea Boots

1 Pair Of Leather Loafers

Black shoes are dressy, but a brown option lets you swerve that smart-shoes-and-casual-trousers look so beloved of guys queuing for bad nightclubs.

“Gucci horsebit loafers are a classic and despite several different designers at the helm, they’ve always remained at the label’s core offering,” says Courcey. “Brown loafers sit better with navy trousers or tailoring in lighter shades.”

Gucci Horsebit Leather Loafers, available at Liberty, priced £455.

Gucci Horsebit Leather Loafers

1 Pair Of Minimalist White Trainers

A swoosh doesn’t work everywhere. Sometimes, less is more. “Common Projects sits in a nice place between the simplicity of Stan Smiths and the intricacies of Nike Air Maxes,” says Courcey. “There’s recognisable branding, but the streamlined designs have become something of a trademark in themselves.”

Besides the brand prestige, there are multiple opportunities to wear. “In addition to standard casual looks, we’re seeing a lot of relaxed suit-and-tee combos being anchored with plain white trainers.”

Common Projects Original Achilles Leather Sneakers, available at Mr Porter, priced £265.

Common Projects Original Achilles Leather Sneakers

1 Pair Of Classic Black Trousers

We’re spoilt for choice as tailoring embraces the colour wheel. But for core wardrobe looks, nothing trumps black. “Black tailoring is the backbone of every formal look, and black tie events are a whole new ballgame,” says Courcey. “But if you’ve got a decent pair of trousers, they’ll sit just as well with a tuxedo jacket as they will with a Comme des Garçons coach number.”

But only if you nail the fit. “Opt for a relaxed, slimline silhouette. That way, even if you do gain a couple of Christmas pounds (and then lose them), they’ll still flatter your shape.”

Dries Van Noten Phillip Tapered Wool Trousers, available at Mr Porter, priced £345.

Dries Van Noten Phillip Tapered Wool Trousers

1 Mechanical Watch

“A good Swiss watch has value across the board,” says Courcey. “Not only are you adding the stamp of world-renowned to a look, there’s something romantic about saving something for the next generation.”

But such sentiment needn’t require a Patek Philippe price tag. Mid-level brands offer high-grade mechanisms that can rival the big luxury maisons – a Cartier may win bragging rights, but it doesn’t always guarantee bang for your buck.

Junghans Max Bill, available at The Watch Gallery, priced £725.

Junghans Max Bill

1 Black Blazer

Every man should own tailoring that can simultaneously complete smarter looks and upgrade more casual ones. “A black dinner jacket can be worn in full coordination with black trousers, white shirt and black tie for a red carpet-worthy ensemble,” says Courcey. “But it can also take jeans and a tee to an evening drinks reception.” Ignore this season’s oversized trend and steer snug. “A more relaxed fit can look cheap.”

Burberry London Black Slim-Fit Mohair Hopsack Blazer, available at Mr Porter, priced £650.

Burberry London Black Slim-Fit Mohair Hopsack Blazer

1 Pair of Selvedge Denim Jeans

Most men own a pair of jeans. What most don’t own however, is a pair that can weather the years thanks to heavyweight fabric. “Raw selvedge jeans not only last, but develop unique fades as you break them in. The Japanese variety is often seen as a world best and as such, is worth the investment.” Unwashed indigo looks brand new for longer, stonewash can be up-and-down trendwise and black fades – and not in the good way.

A.P.C. Petit Standard Slim-Fit Dry Selvedge Denim Jeans, available at Edwin, priced £140.

A.P.C. Petit Standard Slim-Fit Dry Selvedge Denim Jeans

1 Peacoat

Bomber jackets tick the casual box, a trench coat will turn office heads and shearling is always cool. But what to wear for a more polished yet warm ensemble? A peacoat. “This menswear classic will sit in your wardrobe for years,” says Courcey. “And always adds instant smartness to your look, be it a suit or something more casual.”

Saint Laurent Slim-Fit Velvet Trimmed Peacoat, available at Mr Porter, priced £1,450.

Saint Laurent Slim-Fit Velvet Trimmed Peacoat

Grand Total: £9,888.70