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What To Wear On Casual Fridays

17 Feb 2022

What To Wear On Casual Fridays

By James Shackell

In a post-COVID world, office dress codes have relaxed slightly. Casual offices have become a little more casual, and even the starchiest corporate firms are beginning to loosen the top button every now and then. Still, if you’ve been a suit-and-tie guy most of your life, it can be hard to know what to wear on casual Fridays. Most firms still have an invisible line marking the point where ‘casual’ becomes ‘too casual’. For reference: thongs will always be too casual.

So what can you wear on casual Fridays? And how do you walk that line between playful and professional? Let’s dive in and find out.

Follow Your Boss

If in doubt, follow your boss’s lead. That’s good advice for any office, but especially when it comes to casual Fridays. If your boss shows up in a hoodie and jeans, you should feel comfortable doing the same. Take a look at your colleagues, too. They’ll give you a guide on what’s appropriate and what’s not. Remember, there are no hard-and-fast rules for casual Fridays. It always comes down to context and culture.

Chelsea Boots

If we had to recommend one shoe to replace your 9-5 lace-ups, it would be the humble Chelsea boot. Chelsea boots ride that line between casual and professional, which is what makes them so versatile. The only choice you have to make is full leather or suede. With their pointed toe, a pair of brown leather DEXTER Chelseas are a slightly dressier option. You can match these with khaki chinos, button-up shirt and a crew knit. For something more relaxed, try the MADISON in suede. Just pair these with some cuffed indigo jeans, a chambray shirt and a nice watch.

Suede Chukka Boots

Chukka boots are slightly more casual again, but with the right styling they’ll slot into pretty much any workplace. Suede Chukka boots, in particular, give you that added texture and warmth. A pair of suede BECKETT Chukkas is a fantastic addition to your collection; you can wear them under cuffed chinos or jeans, and all they really need is a crew knit and navy Harrington jacket to complete the look. If your Casual Friday leans very casual, consider some khaki suede IDAHO Chukkas, too. That thick, white rubber sole looks great under dark denim.


Men’s sneakers are a tricky one for Casual Fridays. Technically, they’re casual, so you’re in the clear. But we still wouldn’t recommend wearing your beaten-up sand shoes around the office. You want clean, sharp and stylish. Not grubby and falling apart. Avoid canvas sneakers for this reason, and stick to styles like the RUDY in White or the DECO 2.0 in dark grey nubuck or full white leather. When it comes to styling, leave the jogger chinos at home and try slim-fit indigo jeans, neatly cuffed. These go well with either an Oxford shirt, or a simple business shirt under a navy crew knit.  


Generally speaking, you want to ditch the dress shoes and lace-ups for Casual Fridays. You’ve got plenty of time to wear them Monday to Thursday. But with its chunky heel and wider toe, a quirky choice like the burgundy leather ROONEY can work. You just need to dress them down a bit. Try dark, slim-fit jeans with a neat double cuff, white collared shirt and grey knit, or maybe navy chinos with a khaki green Oxford shirt. Balance the formal shoes with layers and accessories: a wool trench, trucker jacket, tool watch and open collar


When the mercury rises in summer, thick leather Chelsea boots might not cut it. This is where something like the espadrille can really shine. They’re lightweight and casual, but still smart enough for casual Fridays. Most offices will draw the line at shorts, but you can always throw some CABO espadrilles, or even COSTA slip-ons, under high-cuffed tan chinos. All you need to finish the look is a button-shirt or linen shirt. Small flag: some offices will have rules around socks, so double check before you invest in a pair of espadrilles for Casual Fridays.

Casual Friday Mistakes

The biggest mistake you can make with Casual Fridays is dressing like it’s a casual Saturday. You’re still at work. It’s still a professional setting. So you need to elevate your casual look slightly. A good pair of boots is a great way to start, but don’t forget accessories, either. A dive watch or classic tool watch will help sharpen your outfit, and you can swap out that briefcase for a leather satchel bag. Avoid anything you’d be comfortable eating Doritos in. That usually means tracksuit pants, thongs, sand shoes, old hoodies, threadbare tees.