Up-Down Dressing

Fashion’s shift towards the streets is understandably concerning for the man who’s spent half a decade cultivating his tailoring collection. But just because Alexander Wang and Christopher Shannon have turned the runways on to the joys of looking like you’ve either just left a rave or the gym, that doesn’t mean you need to send those double-monks and three-pieces to storage.

High-low, or up-down, dressing is the art of combining your formal and casual clothing in a way that strips the former of its stuffiness, and the latter of its lackadaisical appearance. But striking the right balance is tough. For every Justin Timberlake, accessorising a perfectly cut two-button with white leather trainers, there’s an Ed Sheeran, looking like he turned up late to a family wedding and had to wear his dad’s spare suit with the Air Jordans he wore on the train.

Avoid making the same mistake by following our guidelines, which will ensure your style’s up-down, not down and out.

1. Trainers & Tailoring

This seemingly simple combination too often veers towards looking like a salesman who changed into his comfy shoes for the commute home. Firstly, the suit; it should fit like a glove – smart shoes can play down extra material, but trainers won’t – and you should steer clear of anything that’s too out there. The sneakers are enough of a statement without adding in bold Etro checks or a neon paisley pocket square.

The same rules apply to your footwear. Keep technical trainers in your kitbag; this is where you want to unleash those monochrome leather sneakers you dropped half a month’s rent on. White should be your default option – a pair of Stan Smiths will sit happily beneath anything from your formal black tailoring to your everyday navy suit.

Playing with colour and fabric is a more advanced move and as with your formal shoes, should offer a contrast in texture. Try suede with flannel, or canvas with linen to keep your skin breathing when the sun starts shining. Just make sure you invest in some fabric protector to keep what’s on your feet looking box fresh; beaten up Converse and a skinny suit is a little too mid-noughties indie front man.

Yet most importantly, you need to wear this combination with rock-solid confidence. Lose the socks, roll the cuffs, go tie-less – just do it with a sense of swagger to show people that you know the rules, you just don’t follow them.

Men's Suits and Trainers Combinations - Outfit Inspiration Lookbook

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2. Suits & T-Shirts

There’s a reason this is the uniform for most fashion designers; it lets you show off both your wardrobe nous and the fact that you don’t have a boss demanding you follow his buttoned-up dress code. Again, opting for timeless, neutral suiting is advisable here and will win you the benefit of the doubt if you don’t quite nail the fit or colour matching.

Monochrome should be your first step on the collar-less road – a grey suit and white tee is a tough thing to mess up – but as your confidence grows you should start experimenting with colours and patterns.

It’s best to keep the eye-catching stuff to your base layer (i.e. T-shirt), as there’s less of it on display, and stick to classic crew necks over anything that plunges towards your navel. You’re not at a Miami pool party now – which is also why, on no occasion, should you be tempted to tuck your tee into your suit trousers.

As an advanced move, try a longline version for a smarter take on reverse layering, or even a baseball shirt, like we saw on the Tiger of Sweden SS15 runways. Just don’t be tempted to add the cap as well.

Men's Suits and T-Shirts Combinations - Outfit Inspiration Lookbook

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3. Blazers & Shorts

Despite the short suit’s increasing prevalence, calves out tailoring isn’t for everyone. Or, really, anyone who isn’t sipping an espresso and preparing to step back astride their scooter.

Non-matching shorts and blazer separates, on the other hand, are much easier to pull off and will produce outfits that hint at the Mediterranean – even if you’re barbecuing beneath increasingly angry skies.

Nailing your choice of shorts is key: on or below your knee and you look like you’re on safari; too high up your thigh and, well, you’re wearing short shorts. And even a bespoke Italian blazer won’t salvage your look.

You also want to avoid looking too matchy-matchy. Cream shorts and a navy blazer will draw the eye to your torso, not your pins, and make your legs appear more tanned. On which note, if you haven’t recently been away on holiday and your skin is looking a little pasty, a bit of fake tan or bronzer pre-unveiling will hide a multitude of sins.

Men's Shorts and Blazer Combinations - Outfit Inspiration Lookbook

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4. Commute Coat & Your Sunday Uniform

Throwing your office outerwear over off-duty staples can make it look like you were in a rush to leave the house and grabbed the first coat by the door on your way out. So, as with any high-low combination, the balance needs to appear deliberate.

The simplest approach? Upgrade your casual wear. If your topcoat is slung over a pair of slimline wool joggers and a leather-panelled sweatshirt, suddenly it looks like you picked the weather-beating outerwear for practicality but haven’t sacrificed style for comfort.

An unbelted trench/mac or slightly oversized, raglan sleeve overcoat plays up that relaxed air, but making sure the sleeves are fitted (and there’s a flash of sweatshirt cuff peeking out) tempers the roomier shoulder and body so it doesn’t look like you’re wearing a hand-me-down.

As for what lies beneath? Stick to high-end streetwear staples such as marl loopback sweatshirts, luxe hoodies (cashmere and merino wool versions look as good as they feel), zip-up track tops and soft cotton tees for your top half, and either broken-in jeans/chinos or on-trend tailored sweatpants for the bottom.

This is a styling technique that was extremely prevalent on the AW15 runways, so it’s well worth taking the time to nail it now, in advance.

Men's Smart Coats and Casual Clothing Combinations - Outfit Inspiration Lookbook

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Gilet & Blazer

A combination that has seen its popularity soar over recent seasons, teaming a gilet with a blazer nods to spring’s unpredictable weather and helps dial down the formality of your tailoring.

If you’re wearing a full suit, the gilet should go over the top of your jacket. It’s important to opt for neutral or subdued hues here; a big block of colour that ends abruptly at your shoulders and waist does no favours for your physique.

However, separates offer more leeway. Keep the look dressed-down and relaxed – this is the place for an unstructured or unlined blazer, not anything too formal and full of shoulder padding.

Throw a lightweight, technical gilet (Uniqlo’s Ultra Light Down versions come highly recommended) underneath for a contemporary twist on the waistcoat that will actually keep you warm.

Feel free to play with the colour of your vest as, again, there’s less on display and your blazer’s naturally tailored shape will ensure you don’t appear too boxy.

Men's Blazer And Gilet Combinations - Outfit Inspiration Lookbook

Mango AW14digel aw12mango man winter 2014massimo dutti aw13mango man fall 2014mango man aw13pepe jeans aw13sandro aw12suitsupply aw14banana republic aw15brunello cucinelli aw15mango man aw12
Final Word

High-low dressing will breathe new life into a wardrobe that’s feeling a bit uninspired, and gives you a chance to utilise your key pieces in new ways.

The most important thing, though, is confidence. Too many men dress up-down by accident, wearing a pair of knackered trainers with their suit because they couldn’t find their proper shoes, or grabbing a bulky, pocket-ridden hiking jacket because it was the nearest thing to the door. You don’t want to join them.

It’s also a look where fit becomes even more vital. Wearing your casual staples with a perfectly tailored suit that brushes the top of your shoes and sits snugly against your shoulder is a power style play. Yet even an inch of extra fabric makes it look like you just pulled clothes out of your wardrobe at random.

What contrasting combinations do you regularly utilise, and where do you think the line lies between playing with style rules, and falling foul of them?

Let us know in the comments section.