When it comes to buying stuff, people will often say: “buy the best one you can afford.” This is sound advice, but it can also lead to extravagance. Some items will repay an initial investment much more than others. You don’t want to wear cheap, nasty underwear, for example, but it does wear out regularly, so hand-sewn, silk briefs are hard to justify, price-wise (though maybe you have a special reason).

Here are five items that are worth spending your money on, and why.

A winter jacket
Quality outerwear is always a good buy, simply because it’s the top layer of an outfit. This means it needs to look good (as it will always be seen), and needs to be tough (because it suffers the most wear and tear). A well-made jacket, made from high-quality materials, can last for decades, and will only look better with time.

Look for heavy, pure materials (100 per cent wool, cotton, thick leather or suede); heavy-duty zips; solid buttons with reinforced backing and non-synthetic lining. The country of manufacture should be a place where you can imagine them making a good jacket (think England, Germany, Japan or Italy).

I’m not suggesting blowing your paycheck on a pair of Yeezys, that’s not a good investment. But having at least one good pair of Goodyear welted shoes will always pay off in the long run. They are made so that the sole can be replaced over and over, so if you look after the top part of the shoe (the “upper") the shoes can last for decades.

Look for brands that are made in England (they have always made the best) and are full-grain calf leather.

Most denim out there is total rubbish. Look for proper selvedge denim that has been woven on vintage shuttle looms. Not only is the weave tighter and sturdier, but a proper twill weave interlaces the cotton yarn so the fabric doesn’t begin to disintegrate when you wear a hole in your favourite pair.

You can trust almost any Japanese brand, but there are a few great retailers of Japanese denim in Sydney (Corlection), Melbourne (Pickings and Parry), Adelaide (Right Hand Distribution) who you can trust to help with the nitty gritty.

A good pair of sunglasses is always worth the extra cash. Frames made from high-quality plastic (acetate) or metal (titanium or steel) are more durable and fixable than cheap frames. More importantly though, lenses should be clear, scratch-resistant, and more protective than cheaper varieties. Plus, they look better. If you’re one of those people who says “I always lose sunnies”, that’s fine. Buy cheap ones, look bad and go blind – very cost effective.

Look for anything made in Japan or Germany (there are also a few good French and Dutch brands).

My picks:
Matsuda 2830

A lightweight or “shirt” jacket
This could be anything from a denim jacket to a lightweight Gore-Tex outer shell. A “shirt jacket” is really just a shirt made from heavier cotton featuring extra pockets – some flannos are good examples. It’s a year-round garment, which is great on rainy or cool summer days and can be worn over a woolen jumper in the dead of winter (it’s the perfect windstopper). Many people don’t see the point in investing in such a seemingly insubstantial garment, but cheap, lightweight fabric doesn’t keep the wind out, and usually falls to bits. You can approach Finery Company via Instagram to get one custom-made for yourself.

It’s all about the fabric here, but also make sure the stitching is fine and tight. Details like the collar and cuffs are an indicator of how much care has been taken in making the jacket.

My pick:
Beta Lt Jacket

Bonus tip: haircut
Don’t get a cheap haircut. Most of the time people can see your hair. Cheap haircuts almost always look like cheap haircuts, so it is a quick way of ruining your look. Some (but very few) people can get away with it, but even if you’ve got Kennedy hair you should cough up for a decent ’do – you can bet he did.

My pick:
Pickings & Parry

Double Monk is a purveyor of fine menswear, with stores in Melbourne and Sydney.

This article was updated on February 14, 2019.