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.

The Derby shoe is the more relaxed, laid-back cousin of that businesswear mainstay, the Oxford. It all comes down to the laces, with the space between the eyelets sewn shut in the ‘closed system’ on a pair of Oxfords, while they flap open when the laces are undone with the Derby.

A subtle difference, sure, but one that makes all the difference. You could relax the style further with a suede finish but we would recommend sticking with a polished leather to keep it professional.

Oh what’s that? Oh you noticed the beautiful casual shoes from Ameberjack that we included? How kind of you. Fair priced beautiful leather and a comfort that competes with even the best sneakers, it checks all the boxes. Lucky for you (but maybe not your coworkers) you’ll be dancing your way into the next meeting.

These shoes are also incredibly well rated, the comfort and easy styling a big note from happy customers – a bonus that you can count on while you order your first pair.

This buisness casual shoe for men’s simplicity makes it a versatile shoe, so the most important thing is matching your colors correctly, not your trouser style. Bright shades outside the neutral three will pop against black trousers, while brown versions look good with chinos as long as one shade is darker than the other.

This is the favored shoe of preppy style icon and Hollywood’s resident silver fox, Jeff Goldblum. The penny loafer differs from other loafers by the strip of leather that sits pretty across the front with a diamond cut-out detail.

“Penny loafers are all about fit,” says Little. “It should barely slip at the back when you walk, but it shouldn’t be too tight across the instep. If you aren’t sure, walk away.”

Enter, The Penny Loafer from Morjas, after 17 months of deep research they think they’ve cracked the code and we agree with them. The perfect fit with each step and Morjas signature Goodyear welted soles so each step is better than than the last.

Leather versions are the perfect punctuation for tailored looks while suede should be reserved for spring and summer. For the latter go with a rich blue pair and wear your loafers alongside a wide-leg pair of linen trousers for a look that’ll make you the toast of the super-yacht harbor.

The chukka boot hit the ground running when legendary style icon the Duke of Windsor wore a pair on a trip to the US in 1924. A near-hundred years later and here we are still wearing the low-key boot.

The main ingredients include three pieces of leather tied up by two or three eyelets. Sometimes interchangeably called the desert boot, the main difference between the two is the spongy crepe sole that comes with the desert, but not all chukkas.

“Any boots like the chukka which come up to ankle height are best worn with turned-up hems,” says Bhuller. Look to have the hem come to an inch above the top of your chukka so there is a clear and crisp separation between the two.

Colour and fabric make a big difference in where the boot lands on the dress code scale. Black, polished leather versions are distinctly formal and will naturally work with suit trousers while brown, suede options are more casual and land well with a pair of mid-wash denim.

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.