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Style Advice

The best jackets to own in your 50s

The best jackets to own in your 50s

Jackets serve many a purpose: they’re your armour against the elements, an expression of your personal style, and the first thing people see you wearing in the cold-weather months. So lest you’ve been throwing on any old outer-layer in arm’s reach, we’d challenge you to give yours a bit more consideration. And that involves factoring in your age. 

Now we're not suggesting that age should in any way limit your personal style. There is a way to style every outerwear style during any period of your life – in fact, we've seen 50-somethings style bomber jackets more stylishly than the coolest 25 year olds. All it takes are a few style tweaks and the right level of confidence. 

That said, there are certain styles you’ll get the most wear out of during your 50s – and if you invest in high-quality iterations, you’ll be able to keep hold of them well into your 60s. We tapped resident style expert Toby Standing to walk you through his favourites. Your 50s are about to get a lot more stylish. 

Chore jacket

Why it works

My dad is currently in his 50s, and he lives in his chore jacket. It’s such a cool, fresh style and its timeless design means it works for every age. In fact, it might feel slightly unexpected, but that’s part of its appeal. It works great as an alternative to a blazer, but the canvas fabric means it will feel less stuffy. Plus it’s insanely easy to dress up or down.

What to look for

Stick to a more classic style – one made with cotton twill in a regular cut. Avoid any styles with zips while you’re at it. In terms of colour, it tends to work best in French blue, navy, or olive green. This is a timeless, age-old classic, so no need to reinvent it.

How to style it 

In addition to wearing it with casual everyday styles, I like it in a place of an unstructured blazer over a crewneck sweater with chinos. It’s a more interesting take on office style.

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Overcoat

Why it works

It’s an undisputed classic. Think of it as a blank slate for you to project your personal style, whether you tend towards smart or casual pieces. And just because it’s timeless, doesn’t mean it has to look dated – there are fresh ways to style it in your 50s (more about that below). It also works ub nearly any setting, so you’ll have this coat in your rotation for years to come. 

 

What to look for

Go for a more refined style – think fitted instead of oversized. If you want a more classic style, opt for a single-breasted silhouette. If you want one that tilts slightly younger, go for a double-breasted style, as they’re having a moment and are still timeless. 

For maximum versatility, choose a style in grey, navy, or black, and avoid patterns, unless it’s something classic like a Prince of Wales check. Fit is the most important detail; you want a style that looks neat and sharp. It doesn't need to be made to measure, but it should fit you like a glove (more about that in our guide to how an overcoat should fit). 

How to style it 

The overcoat looks particularly sharp with a rollneck or half-zip for every day. In terms of trousers, it works as well with casual chinos and jeans as it does with formal trousers. And when that next special event rolls around, you’ll want to pair it with a suit for the ultimate dapper look. If you can’t tell, we think this coat goes with just about everything, so you’re free to wear it in whatever way you feel most comfortable. 

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Waxed Jacket

Why it works

Waxed or field jackets work well at every age, but if you don’t own one already, your 50s are the perfect time to see what all the fuss is about. They’re handsome, practical, and a stone-cold classic. They’re also great for time spent outdoors, thanks to their warm, waterproof designs and surplus of pockets. You can also wear it to the ground, and it will still be repairable. It’s a jacket for life. 

What to look for

Look for waxed jackets that finish at just below the waist. The shorter ones tend to look best and be the most wearable. Anything that’s too long will look like a hunting jacket. You’d be hard-pressed to find one not olive or navy, so stick to those colours. 

How to style it 

Heritage jackets work well with workwear pieces – think indigo denim, Henley shirts, textural knits, and boots. The shiny wax finish means it will look great with anything textured. These jackets look best worn in, so don’t be afraid to wear yours on repeat. 

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