Miserable, grey, wet, cold. We get it—fall and winter can be a drag. But if this is all you see when you open your curtains in the morning, perhaps you need to change your outlook or, at the very least, your wardrobe. The best place to start? Make sure you have those high-quality cold-weather pieces—the ones that perhaps cost a little (or a lot) more but that will have your back for a long time—maybe even for life.

Investment pieces require a significant financial hit initially but will keep giving back over a long period of time. These are the pieces you wear again and again over decades. They’re versatile, don’t date quickly, and are built to last for the long haul.

So, what are these pieces in the context of autumn and winter? We’re glad you asked. Here are our top luxury investment pieces for the cold season and the reasons why they’re well worth the money.

Goodyear Welted Boots

Winter conditions can be harsh on footwear. It’s going to be wet, it’s going to be cold and there is going to be dirt. You need footwear that’s up to the challenge, and Goodyear-welted boots are quite simply built differently.

These boots use a special stitch-down construction to attach the uppers to the soles. Producing footwear this way is labour-intensive, so it commands a higher price. However, it also makes shoes and boots extremely durable and allows for easy resoling.

What all of this means is that a single pair of Goodyear-welted boots will likely last you much, much longer than a lesser alternative.

A Bag For Life

Aspinal of London

No, not that kind. We’re not talking beefed-up plastic shopping bags to carry your weekly shop to the car. What we’re interested in are robust weekend bags that are built using quality materials and stitched together with great care and attention. Imagine the sort of bag you can use for your overnight Christmas trips from now until you’re old and grey.

A proper weekend bag is a must for every style-conscious man. It should be big enough to carry a couple of days worth of clothes and essentials but small enough to squeeze into an overhead locker. It should also be made from something nice and durable, like heavyweight canvas, leather or suede.

Bennett Winch, Dunhill and Aspinal of London are some of our favourite names in this particular game.

A Special Overcoat

Private White V.C.

Big unstructured overcoats are trending right now, but that’s not why you should buy one. A high-quality overcoat in a versatile silhouette might be the best money you’ll ever spend on outerwear.

This is a garment that will go with anything short of your gym gear. You can drape it over a suit or even a tux. But equally, it can be teamed up with casual outfits, including things at the far end of the spectrum like hoodies and sneakers.

The key is to buy one in a high-quality material and a versatile colour. We like a classic textured wool in grey or a Prince of Wales check. It’s also a good idea to opt for a raglan sleeve, which allows the shoulders to fall naturally for a less structured look that will allow it to pair more effectively with casual pieces.

Drake’s and Private White V.C. currently make some of the nicest versions we’ve seen.

A Leather Jacket

Velasca

Whether it’s a classic black leather biker or a luxurious suede bomber, a quality leather jacket will elevate your everyday looks during the colder months. You can wear it as a standalone piece on cool days or as a layer in the absolute coldest of cold.

The key is not to cheap out. It can be tempting to settle for a low-quality synthetic alternative when you see the prices associated with the real deal, but you’ll only be conning yourself in the long run. See, while a proper leather jacket may cost significantly more, it will also last significantly longer, so take the plunge and you’ll be rewarded over decades to come.

Brand-wise, look at Schott NYC, Saint Laurent, Belstaff and Private White V.C.

Cashmere Knitwear

Velasca

A cashmere knit may not look like much – it can be as simple as a plain grey crew sweater – but it can elevate even the simplest of outfits. The silky soft hand feel and glossy appearance of this high-end knitwear lend a luxurious edge to all outfits, and if you buy your knit in a versatile colour, you can wear it across a surprising amount of your wardrobe.

Can’t stretch to a sweater or cardigan? Fear not. A cashmere scarf achieves the same goal at a lower price point and you can wear it with literally anything. How’s that for impressive bang to buck?

Some Proper Jeans

ASKET

You there! Step away from the H&M jeans rail. That blue stuff in front of you? It’s not denim. Not really. Sure, it looks like what jeans are supposed to look like, but come this time in a year or two, we’d be surprised if they’re still on the go. This is why, for us, it’s always worth investing in the high-quality stuff.

If you want to up your jeans game, look for quality Japanese fabric, a classic straight-leg or tapered fit and a nice versatile wash. Even better, go for raw denim and let your jeans age with you as they mould to your body over time and develop unique wear marks just for you.

A Down Parka

Woolrich

When the real cold bites, an overcoat or a jacket isn’t going to be sufficient to keep you warm. You need something bigger, burlier and, crucially, much warmer. That’s why your big winter coat should be a down parka. But, heads up, they aren’t cheap. Not if you buy a good one.

Down parkas are no joke. Variations of this style of outerwear are used by everyone from polar researchers to mountaineers on Everest. Granted, the ones they’re using are probably overkill for standing around on the sidelines watching your kid play football on a December Sunday morning, but there are plenty of these things designed with regular folk in mind, too.

We’re big fans of Japanese outerwear label Goldwin’s offerings in this department. They’re highly technical and built using incredible materials, but they also tend to feature slightly exaggerated silhouettes that give them a fashion-forward edge. For something more traditional, try Woolwich, Canada Goose or The North Face.

A Gore-Tex Shell

Bad news. It will be wet, and there’s not much you can do about it. Except, that is, to equip yourself with a suitable jacket. A waterproof shell that deflects water droplets from the outside while allowing vapour (ie sweat) to escape from within. This means you stay dry at all times, no matter the weather.

The key here is to buy a jacket made from the right stuff. There are a few brands that make excellent waterproof fabrics, so look for jackets marked with something like ‘Gore-Tex’ or ‘Pertex’.

If in doubt, research and buy from a proven outdoor specialist brand like Arc’teryx, Haglöfs, or The North Face. That said, there are fashion-led alternatives that do the trick. Take Nanamica for example, a Japanese brand that works with Gore-Tex materials to produce outerwear in classic, casual silhouettes.