Best Cost-Per-Wear Investment Pieces in Men’s Fashion

Want to dress well, be economical and be kinder to the planet? Stop spending your money on cheap, poorly made, trend-based tat.

It may seem counterintuitive to buy a more expensive garment if your end goal is to save money, but cheaping out on clothes is a false economy. Subpar materials degrade quickly, badly stitched seams come undone and, ultimately, you’ll find yourself spending again and again when you could’ve just coughed up a bit more for a higher-quality garment in the first place.

Following trends is a good way to burn through money too. Sure, mix in the odd piece here and there if it matches your style, but filling your wardrobe predominantly with classic, versatile pieces you can endlessly mix and match will save you money and futureproof you against the ebb and flow of fashion in the long run.

You don’t necessarily have to spend a fortune to end up with something you’ll get lots of wear out of either. Some small accessories and personal items may not cost that much, but you could end up using them every day for decades.

So, what are these pieces? The ones that will give you the greatest return on investment in terms of cost per wear? Below, we’ve listed our favourite examples of things you can buy once and wear for life (or near enough!). So keep scrolling and get ready to refresh your wardrobe the right way.

A Goodyear welt is a strip of material (usually leather) that runs around the perimeter of a shoe’s outsole connecting the upper to the insole. If you can’t picture that, don’t worry. All you need to know is that this method of construction results in some of the most durable and easy-to-repair footwear out there.

Goodyear-welted shoes and boots tend to command high prices, which might put some people off. But factor in the longevity and repairability and those lofty price tags become much more palatable.

Cared for correctly, a pair of Goodyear-welted shoes or boots could last you a decade or even more. So even if you spend £400, the cost per wear will be relatively low in the long term.

Wool Overcoat

A wool overcoat is one of those rare garments that can be worn with anything and everything. It complements your finery while dressing up more casual pieces, and it hasn’t fallen from fashion since the 18th Century. That makes it a pretty safe bet in terms of being trend-proof.

Are you going to be able to pick up a proper wool overcoat on the cheap? Probably not, unless you buy it secondhand or vintage, but even at full price, you might be able to justify the expense to yourself by considering that you’ll likely still be wearing it when you’re in your twilight years.

Hell, you could even pass it down to your son, and his son after him. If that’s not an attractive cost-per-wear proposition then we’re not sure what is.

Cashmere Sweater

Cashmere is one of the most luxurious materials in the world. It’s soft, silky, breathable and three times warmer than regular wool. And that’s not all, because while it does require special care to keep it looking its best, cashmere will hold its shape and resist shrinking far better than wool, making it the better option in terms of long-term wear.

Yes, cashmere is expensive, but even if you just have a single cashmere sweater in your rotation, it’s enough to give simple outfits a little touch of luxury. Plus if you buy it in a nice neutral colour, you’ll be able to wear it with lots of different outfits in lots of different ways.

Proper Jeans

Raw denim is a whole subgenre of menswear with a cultish community behind it. Fully grown men compare notes on thread counts, how best to wash their jeans, how many months you should wait before you do and ultimately how to achieve the perfect fades.

If you haven’t experienced a proper pair of jeans before, it might all seem a bit strange, but we’d urge you to invest in some and find out the joy and the durability firsthand.

Not only do raw denim jeans last for ages thanks to their tough heavyweight fabric, but they get better with age. Over time, the indigo dye will fade away in high-wear areas, creating distinctive fades and whiskers, and giving the denim a patina unique to the individual wearer’s daily life.

With this in mind, you’ll probably be wearing them for many years, making them great value for money in terms of cost per wear. Not only that, if you buy from a brand that operates a repair service you can continue to restitch and patch up your prized denim, making it even more unique as the days go by.

Leather Jacket

Leather jackets can be expensive due to the cost of the materials and the level of craftsmanship involved. It’s not uncommon for a quality leather jacket to take more than a week to make, and this is often reflected in the price tag. But as a result of this, leather jackets are usually extremely durable. Buy a good one and there’s a good chance it’ll outlast you. And much like those raw denim jeans, it will only get better with age.

There are lots of different styles of leather jackets to choose from, but for us a classic biker is the best option. Not only is this an iconic style that has been in fashion since the 1950s, but it’s also surprisingly versatile, and can be used to give even the most mundane of outfits a bit of an edge.

Well-Made Weekend Bag

A good weekend bag tells the tale of its travels through all the scuffs, scratches and stains it carries along with its load. But to get to that point, it has to be durable and well-made enough to stand up to the journey.

You might be tempted to cheap out and use a nylon gym holdall or something equally unstylish for your weekend excursions, but we’d urge you to invest in something made with better materials that will ultimately last longer.

Whether it’s leather or heavyweight canvas, a proper weekend bag can easily last a lifetime if it’s looked after and patched up every few decades. So spend the extra cash and get one that you love.

Winterproof Parka

Every man needs a serious piece of outerwear that can completely block out the cold when winter is in full swing. With its tough outer fabric, insulation, long cut and trimmed hood, a classic Arctic parka is the best tool for the job. And because it’s only in use for half of the year, it should last you many years, decades, or perhaps even for life. That’s provided you arm yourself with a good one, of course.

There are several brands that have made a name for themselves through this type of outerwear. If you want the best of the best, and to guarantee longevity, you should take your money to one of them. Labels like Woolrich, Moncler and Canada Goose are famous for their parkas. The latter has long been the go-to coat for those working in the coldest conditions on earth. Think Arctic researchers, polar explorers and wildlife cameramen.

If you really want to maximise your cost-per-wear value, buy second-hand, or shop around for something slightly cheaper that doesn’t sacrifice quality. Patagonia, Fjällräven and The North Face make some great options that are a little more wallet-friendly.

Navy Wool Suit

A well-made wool suit in navy is incredibly versatile and can be worn in lots of different ways, making it great for getting the most out of your money. You can buy one off the peg as long as the material is good and the workmanship is solid, and then have it tailored for the perfect fit. This is much cheaper than having a suit made to measure but essentially achieves a similar result.

There aren’t many formal and semi-formal settings in which this type of suit won’t work – it will take you to job interviews, weddings, business meetings, fancy date nights and everything in between. Go for a single-breasted, two-button jacket with notch lapels in a slim-regular cut to keep it classic. This will ensure you can get the maximum amount of wear out of it over the years without it looking dated too quickly.

Wool is the perfect fabric as it can work in all seasons, and you can even separate the jacket and pants, using them as individual elements in different outfits.

Cashmere Beanie

If you live somewhere that sees anything below 10°C, a good beanie is going to rack up serious wear-time each year. Ditch the acrylic ones that bobble and bag out within a week and get yourself a finely knit cashmere version instead.

Not only will it keep your head warm and wick moisture away, it’ll also retain its shape and softness for season after season. Stick to neutral colours like navy, grey or olive and it’ll go with everything you already own.

Minimal Leather Sneakers

If we were to name one type of shoe that earns its keep better than almost any other, it’s the minimal leather sneaker. Crisp, versatile and quietly stylish, they’re the one pair that work with everything from jeans to casual tailoring, and if you look after them properly, they’ll be with you for years.

Go for full-grain or calf leather, a low-top silhouette and a pared-back design in white or off-white. Brands like JAK, Oliver Cabell, Arket and Clae make excellent options that hit the sweet spot between quality and price. Cost per wear? Practically unbeatable.

Leather Cardholder or Wallet

The humble wallet is still a daily-use item for most of us, even in the contactless age. A slim, high-quality cardholder in leather will last years if looked after, and unlike cheap options, it won’t fall apart at the seams after six months in your back pocket.

Pick one with clean stitching, decent structure and a minimalist shape – preferably from a small leather goods brand like Carl Friedrik, Bennett Winch or even Uniqlo’s Premium range. Fewer cards, less bulk, more mileage.

Tailored Wool Trousers

A pair of well-cut wool trousers might not sound particularly exciting, but they’re one of the most versatile wardrobe pieces a man can own. They work with dress shoes and a shirt for smarter occasions, but they’re just as at home with white sneakers and a crew-neck sweatshirt on the weekend.

Choose a flat-front or single-pleat pair in a midweight wool and you’ve got year-round appeal. Mid- or high-rise, with a slim-to-tapered leg, and in a neutral tone like charcoal, navy or taupe – they’ll go with everything and rarely date. The fact they wear better, resist wrinkles and outlive cotton chinos by miles? That’s just a bonus.

High-Quality Sunglasses

Sunglasses are one of those items where it pays to spend a little more. A classic shape like the Wayfarer, Clubmaster or Aviator never goes out of style, and with proper care, a premium pair will easily last a decade or more. They’ll protect your eyes, elevate your outfits and survive countless summer holidays and city breaks along the way.

Steer clear of trend-led shapes and logos. Go for acetate or metal frames with good hinges and proper UV protection, and brands like Persol, Cubitts and Oliver Peoples are hard to beat.

Stainless Steel Mechanical Watch

There are very few things you can wear daily for decades and still expect them to work perfectly, but a good mechanical watch is one of them. Whether it’s automatic or hand-wound, a solid timepiece is built to last, and if properly maintained, can even be passed down to the next generation. That’s pretty hard to beat in terms of cost per wear.

Don’t feel like you need to go Swiss-luxury level to enjoy one either – brands like Seiko, Tissot and Baltic offer great mechanical watches with classic designs and solid movements that punch well above their price point. Choose a versatile design in stainless steel and you’ll have something that works with everything from tailoring to T-shirts, for decades to come.