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Style Advice

How to wear smart casual in different settings

How to wear smart casual in different settings

We hear you – smart casual dressing is a minefield. The fact that it’s broad may make it versatile, but it can also make it tricky to interpret in various settings. To complicate matters further, the lockdowns of 2020 have thrown us into a regressive state where putting on anything other than loungewear feels over the top. 

Right now, even wearing a collared shirt can feel like the height of formality. But since we’re not getting out as much as we might like at the moment, it's a great time to better understand how smart casual dressing can work no matter where you’re heading – you may even be inspired to ditch your sweat suit for a day or two. 

A staying-home smart casual

Just because we’ve been refined to our homes for the best part of a year, doesn’t mean we don’t miss dressing up. Sure, there’s comfort in knowing we get to wear our favourite cosy pieces every day, but sometimes dressing up a little can improve your mood and your productivity. But don’t worry – we’re not saying your comfy dressing days are over.

Charcoal grey joggers with an uncuffed hem feel smarter than grey sweatpants. Pick a good, lightweight cotton and you’ve instantly elevated your favourite at-home piece into an outdoor-appropriate look – one that does indeed qualify as smart casual. Pair your joggers with a rugby shirt and sleek leather Chelsea boots. The straight leg of the trousers and the collar of the shirt draws the eye to the elevated cuts and shapes before you notice that they’re inherently laid-back styles. 

“If you happen to be leaving the house to run errands or meeting up for a walk with friends and you want to use it as an excuse to make an effort, this is an easy look to throw on,” says stylist Freddie Kemp, who styled this look at the stunning Boys Hall. “It’s simple, feels clean and grown up, and the pieces are easy to wear with pretty much anything else in your wardrobe."

A classically smart casual look

There are some settings – Casual Friday at the office, dinner with the parents, first dates – where you know smart casual is the only option. Your old t-shirt and jeans would be too relaxed, and a suit would be over the top. It’s within this gaping spectrum that guys often find themselves baffled. 

“Balancing out your look with both smart and casual pieces is a contemporary way to take on smart casual dressing,” Freddie says. “But if you want to pull off the dress code with ease, opt for clothing that hits the middle mark on its own.” It might not sound as interesting, but there’s less room for error and you’re more likely to feel comfortable in your outfit. 

That’s where cord trousers and a humble knit come in. The two pieces combine luxury textures and look best when worn in rich, seasonal colours. So allow those elements to do the hard work for you and relax into your easy smart casual look. It feels minimal and simple, but this year that might be the perfect way to make a statement. But don’t limit it to out-of-the-house settings – this one will impress on Zoom calls too.

A smarter smart casual look

When it’s time to go out and socialise this winter, we don’t blame you for wanting to make more of an effort. If, like us, you’ve been throwing on whatever’s nearby when you have to nip to the shop, this is an opportunity to hone your layering skills. 

Start your look with a button-down shirt (which might feel like the peak sophistication compared to the old t-shirts you’ve been favouring this year), and layer it under a cable-knit jumper for seasonal appeal. For extra warmth, add a gilet and you’ve got an easy country heritage look that will work in any setting. On the bottom, trainers and smart-yet-comfy trousers with a wider leg bring a more contemporary edge, all while complementing the classic pieces you’re sporting up top. In cold weather, throw on a field jacket or overcoat.

“If you’re missing getting dressed and tend to lean smarter, this is the look for you,” Freddie says. It’s comfy but still looks refined, nodding to country gent style that will work just as well in urban settings. “It’s a look that’s great for afternoon walks or days outside, and you’ll carry on wearing it when life returns to normal.”


Words: Ella White
Photography: Jack Batchelor
Styling: Freddie Kemp