Getting through life in the right shoes is tricky business. And the trickiest dress code in footwear is business casual. Smarter than smart-casual, but less buttoned-up than all-out business, it’s a tough one to define. This could mean softly tailored suits with white tees underneath or a knitted polo on top of stone-colored chinos. But all that hard work nailing the dress code upstairs can be undone by not picking out the best business casual shoes for men.

“Business casual is that treacherous middle ground where you are trying to achieve two things, smart yet relaxed,” says Tim Little, owner and creative director of Grenson. “The best business casual shoes for men can be one of two things,” says Little. “A casual version of a business shoe or a smart version of a casual shoe. The first route, for example, could be a classic brogue but with a casual twist such as a chunky wedge sole, or in a colored suede. Whereas the second route could be a sneaker but in a luxury smart leather.”

Here we guide you through the best business casual shoes for men out there, from chunky chukka boots to precious penny loafers, so you’ll never again be caught out in the wrong work shoes again.

Yes, before you say anything, we know this isn’t a pure oxford boot, but what in life is that straightforward? This boot from Myqvist took the cake for its fine craftsmanship and versatility. The texturized leather makes these perfect all-weather, all-year best business casual shoes for men (harder to notice the wear and tear). They also come with Goodyear welted soles, so you know you can confidently put one foot in front of the other. Now onto some brief history:

The Oxford boot is an extension of the straight-laced Oxford shoe, the boot is typically the same in shape and design with limited stitching except across the toe cap and sometimes running horizontally to the eyelets.

The Oxford boot does have the added bonus of more leather to cover up your mankles though, which makes them a harder wearing alternative in winter months as well as a more casual get-up that can work with jeans when the Oxford shoe would look out of place.

“Perfectly versatile, the Oxford boot gives you the option of dressing up or down,” says Bhuller. “Look for heavy round toe shapes for up to date styling”. Wear with an equally hard-wearing pair of wool trousers for the perfect battle armor during the brisk winter.

Sneakers have smartened up substantially over the last decade, and have slowly crept off the tennis court and into the office. But just as you wouldn’t waltz into work like a walking billboard wearing big-logo sweats, your sneakers should be pretty sober, too.

Focus on making an impression with a quality leather finish, and simplistic clean silhouettes, says Jasmine Bhuller, senior assistant buyer at Dune London. “Look for tonal laces to enhance the simplicity and soft, supple leathers with rubber soles for added comfort”.

Despite their rise up the dress codes, even the most minimalist sneakers lean towards the casual end of business casual. Swerve the tie, then, and wear them in a laid-back modern take on tailoring with a white tee or polo subbing for your shirt. If you’re looking to dress down further, a mocha pair of minimalist sneakers will work wonders when tonally paired with some stone-colored chinos.

Thank goodness it was the shoes we took from the monks and not the hard-to-pull-off hairstyle. First created as an adaptation of the sandal for when holy men needed a closed toe to protect their tootsies during manual labour, the shoe has the casual nature of a slip-on with the pointed toe and polished leather leaning it towards the business side of things.

Keep in mind that not all monk straps are created equal. “Single monks are an understated choice,” notes Bhuller, “whilst double monk straps are more distinctive.” Pluck for a clean single strap if you have a formal meeting, leaving the double for weddings and parties when you need to make more of a statement.

“Monk strap shoes have the versatility to go from traditional to trending by simply changing an outfit,” says Bhuller. A firm part of the Pitti peacock’s wardrobe, they work better with tailored looks than jeans, where the dandy buckle and pointed toe can sometimes jar with laid-back denim.

So-called because they found their popularity among the well-heeled party scene that sprung out of the west London borough in the 1960s, Chelsea boots are the quintessential best business casual shoes for men.

“The best Chelsea boots have a beautiful soft curve from the top down to the toe,” says Little. “If it creases heavily across the instep when you put it on, it hasn’t been blocked or pre-shaped and is probably made from cheaper leather.”

Slim jeans that run into the curvature of the Chelsea boot will offer a slick, unparalleled silhouette that goes some way to explain their unwavering popularity. Get away with some subtle rocker vibes in the office by pairing your Chelsea boots with some black skinnies and a white Oxford button-down shirt.

When it comes to different types of shoes, few styles show you mean business like a pair of brogues. You can spot a brogue by the ornamental patterns perforating and lining the leather of the shoe. Despite such over-wrought fanciness, the brogue is an ever-popular shoe around the office, possibly owing to its eye-catching ability while simultaneously keeping your look smart.

Add a contrasting rubber sole and you’ve got comfort and just enough smartness for the modern workplace – a casual sneaker sitting feet-up on the desk, while the brogue on top makes all the business deals.

Brogues are most usually seen in brown leather so the perforations are more visible than they would be with black. These shades of brown look great with indigo denim, especially more decorative styles that bring down the formality of the shoe. Don’t attempt to stick them to black denim though, that’s a minefield not worth traipsing over.