You may think that tailoring with trainers is as stylish as sandals with socks. Well, it is. By which we mean, it’s a move once reserved for guys who valued comfort over style, but is now in vogue, after the fashion set discovered that being comfortable can actually look pretty stylish.

But while the socks-and-sliders thing is best left to rail-thin models and overweight German tourists (both of whom also share a penchant for short-shorts), suits and sneakers is much easier to pull off.

If you follow these guidelines that is, which will keep you looking more like Mark Ronson, and less like the guy in your office who switches into gym shoes for the commute.

Do… Keep Things Classic

You’re making a statement with your shoes, so your suit shouldn’t. This is no time to be revealing that banana-coloured three-piece.

Start with a slim-cut, navy suit and white trainers – the more minimalist, the better. Make sure your trousers are slim- or skinny-fit; flared or boot cut will simply not work. With trainers, or, frankly, anything else.

Mango Man SS15

Don’t… Cheap Out

As with your ordinary work shoes, quality counts. Premium materials, traditional construction techniques and details such as hand-stitching allow you a little more aesthetic wiggle room than rolling up in kicks you found in your supermarket’s discount bin.

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Do… Link Your Look With Colour

The more links you can create between top and toe, the more these seemingly disparate elements gel. Colour is an easy way to pull your trainers into the rest of your look, but keep it subtle; if your suit’s navy, a pop of the same in a logo or lace is better than an all-blue trainer. Otherwise you’ll just look like you’re wearing a onesie.

More subtle is pulling out a shade from your sneakers in your shirt or tie, or even echoing a suede trainer’s soft nap with cashmere around your neck.

Windsor. SS16

Don’t… Embrace The Rainbow

But there’s a limit. Neon trainers are tough to wear if you’re in all-black sportswear. With a suit they just look like your proper shoes got nicked in the gym.

As a rule of thumb, it shouldn’t even be an option to exercise in the kind of trainers you wear to work.

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Do… Show Off Your Sneakers

With formal shoes, your trousers should hit your laces with a little bit of crease in the fabric in front of your shin (the ‘break’). But that’s because people aren’t eyeballing which brogues you’ve copped in the same way they do with trainers.

Take some length out of your trousers, so the hem lands just above the tongue; a roll or turn-up is handy here if you’d rather not visit your tailor for a permanent alteration.

Brunello Cucinelli SS16

Don’t… Get Technical

We’ve got a lot of love for an ‘ugly’ trainer. But while Raf Simons’ Ozweegos are like on-feet spaceships that we’d normally recommend anywhere, they don’t quite work with your Brioni.

The aim of the sneakers and suits look is to take some of the formality away from your tailoring, switching up silhouettes and fabrics to make your outfit appear more relaxed. Technical shoes are too sporty; instead of relaxed, you look like you’re about to start calisthenics in the conference room.

So keep the bulbous, only-a-mother-could-love-em trainers for after-hours.


Do… Tread Carefully At Work

Even if your dress code is lenient, and you can get away with wearing kicks to work, the trainer is meant to lend a louche air to something more often seen as stuffy. So your tailoring should lean more towards relaxed than stiff. Even the sleekest sneakers won’t sit right if you’re rocking a waistcoat, pocket square and lapel pin.

Equally, avoid anything seen on trading floors: pinstripes, wide lapels and padded shoulders. The less structure your jacket has, the more your trainers look like they belong with your tailoring.

Whistles SS16