As style rules go, it’s as outdated as the ban on blue and black, or only wearing joggers in the gym, but when it comes to footwear styles, brown in town is apparently still frowned upon, even today.

Just last year, a study by the Social Mobility Commission found that investment banks were less likely to hire candidates from disadvantaged backgrounds who didn’t wear black shoes at interview. Not attending Oxford probably had more sway than donning the wrong Oxfords, but the report concluded that dress played a “material role” in the selection process as demonstration of “fit” (pun intended).

Even if your line of work is considerably less old school – or you managed to get a job at JP Morgan, which recently introduced a business-casual dress code – footwear remains an occupational hazard. Trainers might be more relaxed than Oxfords, but unwritten rules still apply. And whether it’s discriminatory or not, you’re going to be judged by your footwear. So follow our guide and get off on the right foot instead of putting one wrong.

Oxford Shoes

The definition of formal footwear, an Oxford shoe is standard issue for formal corporate offices. “An Oxford is defined by the ‘vamp’ or front of the shoe being stitched on top of the ‘quarter’ or back,” explains Tim Little, owner and creative director of heritage shoe firm Grenson. “This creates a telltale ‘V’ shape separating the eyelets.”

How To Wear Them

Whenever ceremony is stood on. “In the olden days, an Oxford would be worn in the City and nothing else would do,” says Little. “It’s still a shoe that looks better formal than casual.”

Plain-toe or whole-cut styles skew most formal as adding detail tends to subtract from a shoe’s smartness. But even with a cap toe or broguing, Oxfords pair best with suits or trousers; at a push, a tan pair of Oxford brogues might marry with chinos or denim, but their slenderness makes them uneasy bedfellows with less refined legwear.

“I still never wear anything but an Oxford with a tuxedo,” adds Little. And he doesn’t mean the Texan variety.

Where To Wear Them: In the boardroom, when anything else might get you fired.

How To Wear Oxford Shoes For Work

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Derby Shoes

“This is the opposite of an Oxford,” says Little. “With the Derby or ‘Gibson’, the ‘vamp’ or front is stitched under the ‘quarter’ or back. This means that the eyelets are on two facings that are free to open right up.” That means the shoe is literally and figuratively looser than an Oxford.

How To Wear Them

“Traditionally this was a weekend or country style, as it’s more casual,” says Little. “However, nowadays it’s very popular and often worn as a smart shoe. I’d pair it with anything from jeans to suits.”

The Derby’s beefier profile complements the former, but can also contrast nicely with a tapered, tailored leg for more of a ‘look’; clean styles have a utilitarian, even contemporary vibe that has seen them infiltrate a number of fashion brands’ collections.

In short, the Derby has a broad appeal. “It’s also easier to wear if you have a wide foot or a high instep because the facings open up, as opposed to the Oxford where the ‘V’ only opens so far,” adds Little.

Where To Wear Them: In all except the very stuffiest parts of the City.

How To Wear Derby Shoes For Work

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Loafers

“A slip-on shoe without laces, normally with a moccasin construction, loafers are literally for loafing,” says Christian Kimber, the UK-born founder of the eponymous Australia-based footwear and accessories label.

How To Wear Them

“Loafers go with literally everything – a jacket and tie, or a T-shirt,” says Kimber. “But personally I wear them with chinos or very casual tailoring – not with a formal suit”.

You can slip them on with your two-piece, by all means, but even the dressiest loafers, in highly polished black leather rather than suede, retain an inherent informality. In the film Frost/Nixon, the former president implies snidely that his interviewer’s laceless Gucci Horsebits denote a lack of gravitas.

An extended profile will better balance out tailoring, as will a bit of weight to the silhouette. (Penny loafers can be a bit slight and stubby for this purpose.) Kimber makes his with an elongated toe; he also adds a rubber sole for comfort and longevity.

Where To Wear Them: To paraphrase Nixon, “in a profession where you can get away with something like that”. Anything from banking to real estate to the creative industries.

How To Wear Loafers For Work

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Monk-Straps

You don’t have to be Sean Connery in The Name Of The Rose to work this one out. “Instead of laces, this shoe has a strap to keep it on foot, secured with a single, double or even triple buckle,” says Little.

How To Wear Them

In terms of smartness, the monk kneels somewhere between the Oxford and the Derby. “It’s a formal shoe that looks great with suits and trousers, but can also look fantastic with denim,” says Little.

With its metal hardware, the slightly flashier monk is accordingly worshipped by peacocking Italians, menswear disciples and anyone else who wants to add a little more swagger to their step.

“I like to see a silver buckle on a black monk and brass one on a brown monk,” adds Little. “The strap must be well-designed, not clumsy, and curve properly over the instep so that it doesn’t leave a gap.” That would be sacrilege.

Where To Wear Them: Wherever putting on a suit for work is an aesthetic choice and not an ascetic one.

How To Wear Monk Strap Shoes For Work

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Chelsea Boots

A mid-height boot with elastic gussets to the sides, these striders walk a stylish line between establishment and rebellion. “Most Chelsea boots are constructed from a single piece of leather that’s stitched at the heel, which is a beautiful way to make a shoe – but also really difficult,” says Kimber.

How To Wear Them

Like similarly laceless loafers and monk-straps, Chelsea boots live somewhere in the middle of the smart-casual spectrum: pinpointing exactly where depends on the colour, material, detailing and, well, pointiness of the example in question.

“A chiselled style is more suited to tailoring than one with a round toe, which is more suited to casual looks or denim,” says Kimber. “One that works with both is the holy grail.”

More rock ‘n’ roll than an Oxford or Derby, a sleek Chelsea boot in black or dark brown leather pairs well with a dagger-sharp suit; a tan suede pair – perhaps with a casual crepe sole – will team with your blues for the win. Just watch the heel isn’t too high, Bruno Mars.

Where To Wear Them: If you can pull them off as easily as you can pull them on, then almost anywhere.

How To Wear Chelsea Boots For Work

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Trainers

What makes a trainer office-appropriate? “Low-cut and not high-top, unless your office is dress code-free,” says Kimber. “Plus good stitching and quality leather, inside and out. Tennis styles work well.” Running shoes not so much.

How To Wear Them

Obviously, trainers are casual. So the rest of your relatively smart outfit should meet them halfway. “Don’t wear them with your normal work suit, but with a separate jacket and trousers, and pieces that sit between formal and casual: for instance, a soft-shouldered blazer, Oxford shirt and chinos,” says Kimber.

A formal suit that has a more aggressively ‘fashion’ (i.e. slim) cut works equally as well. Either way, the sneakers (as they are often called in this case) need sufficient clout to offset tailoring without being too clumpy; leather is dressier than canvas.

Pristine white trainers can look smart, but they also draw the eye, whereas darker sneakers can fly under the radar. Some traditional footwear brands – such as Grenson, John Lobb and J.M. Weston – are even making trompe l’oeil trainers with polished uppers that could be ‘proper’ shoes at a glance (albeit for a price).

Where To Wear Them: In ‘creative’ industries – or staid ones that want to appear hip.

How To Wear Trainers To Work

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The Best Trainers To Wear To The Office

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