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The Five Work Shoes Every Man Needs And What To Wear Them With

From classic Oxfords to penny loafers, the essential pairs to give your nine-to-five wardrobe a step up

Work shoes are wardrobe workhorses. Once you lace them up (or, as the case may be, slip them on), they’ll be your companion through your commute to dinner on the other side. All the more reason, then, to consider your choice carefully. Durability is, of course, a priority, but versatility is another factor to consider: ask yourself as you contemplate those Gucci Flashtrek sneakers, can you wear them with most of your pre-existing work wardrobe?

To that end, we’ve compiled a list of fail-safes to help you in hunting down the perfect pair. None of the options below reinvent the sartorial wheel, but that’s hardly the most salient point when your primary concern is impressing your boss. Instead, you’ll find what our fashion team call “The Essentials” – reliable, classic pieces we always have in stock and that you can always rely on. And, because we’re feeling very nice today, we’ve also proffered some handy suggestions for what to wear with them.

Your sartorial freedom of choice might feel a little stifled if you work in a traditional office. Lawyers, brokers and the like are limited to choices that include minor variations of the same theme: a suitshirt and, more often than not, a tie. But that doesn’t mean you can’t stand out from a sea of similarly dressed colleagues. You can play the same game, just beat them at it. Oxford shoes are the obvious choice for obvious reasons. The dress shoe’s basic design tenets haven’t changed in centuries and aren’t likely to undergo a radical revision any time soon.

A decent black pair – Church’s handmade Dubai model, to be specific – will last up to a decade with regular upkeep and, we can’t stress this enough, timely resolings; try not to wait until you’ve run them into the ground before a trip to your cobbler as he’ll likely declare them DOA. And, while the cap toes will render them more durable, if you want to ensure they keep their handsome shape over time, good old-fashioned wooden shoe trees are another good investment.

As for the other constituent parts? Boglioli’s virgin-wool suit will work hard all year round; just make sure to layer it under a correspondingly slim-fit shirt, such as Canali’s cotton-twill variety, to keep lines as clean as possible.

  • Boglioli Grey Slim-Fit Virgin Wool Suit

  • Canali White Slim-Fit Cotton-Twill Shirt

As we descend the scale of formality, there’s more scope for experimentation. Once a strictly “country” shoe, these days Derbies come in all shapes and sizes, but are united in that the lacing across the vamp (top of the shoe) is always open, lending itself to more casual scenarios – a client lunch or catch-up over coffee, perhaps? This Jacques pair from our in-house line Mr P. belongs to the modern school of Derby. It’s built with a rather substantial commando sole and Goodyear-welted, so it’s more robust than traditional varieties and, aesthetically speaking, provides a proportional point of difference. Provided you’re wearing nice (or jazzy) socks, pair them with some cuffed trousers – a full-break is guaranteed to look odd – to achieve the correct balance.

As for the top half, a fine-gauge sweater from knitwear specialist John Smedley is the ideal partner; it’ll be sufficiently smart for a day at your desk and, when the clock strikes 1.00pm, just throw an unstructured navy blazer, also from Mr P., over the top to meet your client.

  • Mr P. Navy Unstructured Worsted Wool Blazer

  • John Smedley Lundy Slim-Fit Merino Wool Sweater

Unlacing your shoes at airport security is a pain we’re now accustomed to. Much like taxes, removing your shoes in a public terminus is part of the social contract of living in modern times. But if you’re a frequent business traveller, your thoughts on the matter are probably more extreme – chief among them: the wasting of precious lounge time. This is why loafers are the only sensible choice for air travel. They’re easy to get on and off, comfortable and smart enough to take you straight to a meeting after landing. Just remember to wear some socks so you’re not plodding about the terminus barefoot – Falke’s specially designed Airport pair are a clever choice.

Like all of John Lobb’s shoes, these suede Lopez penny loafers – a model born back in 1950 – are impeccably constructed with singular attention to detail: the saddle- and hand-stitched apron uppers, for example. Coupling comfort and convenience with classical craftsmanship were also Sir Paul Smith’s prime concerns when he was designing his A Suit To Travel In line. Based on the designer’s popular Soho block, this navy two-piece is cut from high-twist worsted wool, so it’s resistant to creasing and will bounce back into shape when you disembark after long-haul flight.

  • Paul Smith Navy A Suit To Travel In Soho Slim-Fit Wool Suit

  • Maison Kitsuné Slim-Fit Button-Down Collar Cotton Oxford Shirt

For creative types, freelancers or the ever-growing category of WeWork hot-deskers, traditional workwear likely won’t appeal. Sneakers are, of course, an option (see below for further details on that subject). But a pair of Chelsea boots makes for a smarter substitute and a winter-appropriate alternative to Derbies or loafers.

We return to footwear-maker extraordinaire Church’s here: the brand’s Houston pair ticks every classic box – buffed black leather, elasticated sides, pull tabs – but they’re set on diamond-debossed rubber soles for extra grip and a cushioned step. When you’re deciding what to wear them with, channel the spirit of the 1960s and go with top-to-toe black. This decision will allow you to wear a somewhat-risky item of office clothing: jeans. Frame’s L’Homme pair are made from weighty enough denim that they won’t stretch or look sloppy, and paired with a black rollneck, you’ll look every bit the Greenwich Village native.

  • John Smedley Cherwell Merino Wool Rollneck Sweater

  • FRAME L'Homme Slim-Fit Denim Jeans

A visit to MR PORTER HQ might shock corporate types: Triple Ses and Yeezys and Ozweegos. Our dress code is pretty lenient and, where some workplaces would likely deem the audacity of our footwear choices a sackable offence, you can easily wear the sneaker-of-the-week without reprimand – or often even the bat of an eyelid.

Still, smarter sneakers have quickly become standard office fare, thanks, in large part, to Common Projects. The brand’s minimalist Achilles pair is the progenitor of the trend and, when the sartorial history books are written, future generations will credit them with practically single-handedly slackening strict dress codes. Plus, they’re really comfortable. And since they look as good with a suit as they do with jeans, you can wear them with just about anything. For a pared-back preppy look, how about a button-down Oxford shirt and pressed navy chinos?

  • Mr P. Striped Long-Sleeved Cotton-Jersey T-Shirt

  • Norse Projects Aros Heavy Tapered Cotton-Twill Chinos

  • Veja V-10 Rubber-Trimmed Leather Sneakers

  • Grenson Stanley Leather Wingtip Brogues

  • Sperry Authentic Original Burnished-Leather Boat Shoes

  • Gucci Roos Horsebit Leather Loafers

  • Lanvin Cap-Toe Suede and Patent-Leather Sneakers

  • Red Wing Shoes 875 Moc Leather Boots