The Best Stand-Out Smart Shoes

“Smart casual” is not an excuse to throw on some Air Max and hope they magically match your chinos. Unless you’re 16, and it’s 1989, that's not cool. What is cool is picking shoes that make you stand out for all the right reasons. So when you want to be taken seriously, forget trainers and invest in some proper gentleman’s footwear.


Clarks Newkirk Wing

Best for… Winning at Work

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An office shoe should mean business, and boy, does Clarks’s twist on a wingtip brogue do just that. The premium grained black leather upper oozes confidence while the meaty but extra lightweight sole will give you that bit of added height for a commanding presence in your meeting.

£74, clarks.co.uk


GH Bass Weejun Larson Penny Loafer

Best for…Wowing Her Parents

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It’s imperative to make the right impression when meeting your girlfriend’s folks, and while you can’t prepare for the dog humping your leg or a violently snotty sneeze at the dinner table, you can at least wear a world’s-best-son-in-law shoe when doing it. These swanky wine-coloured loafers are sure to be a hit.

£125, ghbass-eu.com


Dr Martens 3 Eye Lace Shoe

Best for… Absolutely Anything

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This autumn Dr Martens, the master of utilitarian footwear, has produced this sleek three-eyelet shoe with a chunky all-black sole to match the tidy upper. What does that mean? Well, it means it’s hard as nails. The simple aesthetic makes it easy to style with both jeans and more fancy attire – in fact, these Docs need not leave your feet all season.

£99, office.co.uk


Padmore & Barnes M387 Willow

Best for… Olympic-Level Pub Crawling

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The Irish manufacturer spent two decades under the ownership of Clarks, when it made the classic Wallabee shoe. Now fully independent, it’s making some seriously nice gear – and this hand-stitched super-comfortable moccasin is no exception.

£125, endclothing.com


Visvim Deck Shoe

Best for… Attracting the Ladies

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It’s said that women judge men by their shoes, so by that logic all the ladies at the club will assume you’re a yacht-owning cowboy taking a vacation from your oilfields to tear up the dance floor. Unfortunately, you do actually need to be an oligarch to afford them. We can but dream.

£705, mrporter.com

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