Nick Wooster’s 15 Best Outfits (And How To Get The Look)

The myth goes that in 2010, Nick Wooster, the then 49-year-old fashion director of US department store chain Neiman Marcus, stepped out of his hotel during Milan Fashion Week and straight into the lens of famed street style photographer Tommy Ton.

In that single second, Ton pressed click and Wooster’s life changed irreparably. The pictures went viral, and he became the granddaddy of Instagram fashion overnight.

Like a hipster Santa, with elaborate tattoo sleeves, a shock of grey hair and the best-manicured beard you’re ever likely to see, Wooster had, and still has, a style all of his own.

A veteran of the industry, the Kansas-native racked up more than three decades at brands like Calvin Klein and Ralph Lauren before swaggering into the public eye. But these days Wooster bills himself as a free agent, and spends his time working on an impressive roster of joint projects with names such as Cadillac and luxury suit makers Lardini.

The Look

So what was it about Wooster’s street style that grabbed Ton in that moment? Our money is on his ability to make most high-fashion pieces appear miraculously wearable.

His trousers are often loose with high crops in a reliable selection of neutral colours, leaving up-top to do all the hard work. Oversized jackets are a big player in Wooster’s wardrobe, usually in cuts that emphasise his muscular shoulders. Expect herringbone overcoats and monster leather jackets with shearling seemingly made out of a whole flock of sheep.

Putting paid to the idea that they’re seldom for men beyond a certain age, he’s also a fan of shorts, often in a longer length than the current industry standard of just above the knee. Then, to finish off, he’s rarely without a pair of shades or a chic scarf for a look that cements his position as cosmopolitan king of international fashion weeks.

Inspiration: Pharrell Williams, George Cortina, Andy Warhol
Go-To Brands: Maison Margiela, Rick Owens, Thom Browne
Follow Him: @nickwooster

Burgundy Says It Best

Nick Wooster’s style has more than a flash of fashion hypebeast about it, but he also does the more classic, timeless looks extremely well. The cropped, single-breasted peacoat here offers the ideal top layer for brisk walks between shows, while the burgundy hue and natty polka dot scarf stop it from looking boring. Down below, his pleated trousers add some extra detail thanks to their textured material and two-tone design, before bringing it back with a matching pair of oxblood Derbies finished with a rubber sole for a little sprinkle of sprezzatura.

Millennial Pink

To key to wearing pink, or any statement hue for that matter, is to pick out an item in that shade first and then work the rest of the outfit around it. Light neutrals provide the ideal base for a colour pop, as evidenced here by Wooster, who has deployed the very millennial tone on a suede bomber jacket worn over a grey T-shirt, tonal trousers and white sneakers.

Nick Wooster's 15 Best Outfits

A Herringbone Hurrah

The structure you get from a shirt or overcoat is smart, but it can also be stifling. It’s for this reason that Wooster often experiments with pieces that go against the norm. Take for example this herringbone jacket, which features a relaxed cut and nonchalant shawl lapel. Despite the flowing feel, the fit itself still hits the mark, with carefully cuffed sleeves and shoulders that slope rather than hang off the body. Granted, the safety pinned cardigan underneath may be a step too far for the everyman, but there’s still plenty to learn.

Nick Wooster's 15 Best Outfits

Saying Hi To High-Low

The penetrating rise of streetwear, for which Wooster can claim some responsibility, has led to a trend for high-low dressing. The combining of traditionally smarter pieces with sporty and casual elements has overhauled the tailoring game, with T-shirts now a regular fixture alongside suits. Flipping this on its head, here Wooster has opted for a casual bottom half, with joggers counteracting a more structured jacket. The key here is in tying everything together with some tonal dressing and footwear that isn’t running shoes. Bravo, sir.

Nick Wooster's 15 Best Outfits

Fashion Week Camo

At five-foot-five-inches, Wooster is shorter than your average guy, which makes dressing for your body type all the more important. Understanding that skin-tight fits do just as much damage as swathes of excess fabric, the fashion week cool cat always hits the hallowed sweet spot in between. Case in point: this separates look, which taps frequently overlooked green tailoring. He may have decided to ignore the buttoning rule of ‘sometimes, always, never’ with his jacket, but we’re willing to let that slide considering the overall effect is on the money.

Nick Wooster's 15 Best Outfits

Prince Of Wales Head To Toe

A prime example of Wooster’s penchant for putting a new spin on menswear classics, here the Internet superhero decided to eschew the usual three-piece combination by dropping the waistcoat in favour of checked slip-on sneakers. To stop the look from appearing like something thrown together by an attention-seeking blogger, the rest of the outfit is kept simple and monochrome, with a black watch and belt contrasted by a white grandad collar shirt, pocket square and even facial hair.

Nick Wooster's 15 Best Outfits

Meet The Grandparents

Usually, wearing a pair of shorts that creep below the knee is a surefire way to channel granddad-at-the-garden-centre vibes. Not when Wooster does it. A master of proportions, here the purposely exaggerated bottom half is balanced out by a well-fitting T-shirt up top that shows of his heavily tattooed arms. This is also time to appreciate The Woost’s hair, which is kept high and tight for a finish that’s fuss-free, but ultimately flawless.

Nick Wooster's 15 Best Outfits

Classic Fashion Frayed

At first glance, you’d be forgiven for dismissing this as a fairly underplayed monochrome look from Wooster; the white trousers popping against his classic black Derbies and blazer with the collar overturned. But on closer inspection, there’s a deliberate ragged and distressed effect on the jacket, with the frayed edges adding some rock ‘n’ roll grit and much-needed texture to an otherwise sleek look. It’s okay to look like you got dragged through a bush, just make it ‘fashion’.

Nick Wooster's 15 Best Outfits

The Big Boy Jacket

Though not all of Wooster’s outfits are replicable for the everyday man (we give you exhibit A), there are more than a few lessons to learn here. If you’re a shepherd, it’s to never leave your flock unattended while he’s around; if you’re a regular guy, it’s that any outfit can work with a bit of confidence and swagger. And even on the snowy streets, Wooster is not without his signature sunglasses, because UV rays are year-round remember.

Nick Wooster's 15 Best Outfits

Two Tone Terrific

Those sailors got it right when they pegged navy and white to the colour combinations mast. It’s a classic pairing that can work for just about anyone, but for a more contemporary take, swap out stark white for cream. Wooster does this to excellent effect, setting sail in a block-design coat worn over tonal trousers. Once again, easy-going accessories in the form of a loosely tied scarf and classic sunglasses stop this look from verging on avant-garde, bookended by minimalist sneakers.

Nick Wooster's 15 Best Outfits

Del-Boy Deviant

One of his many famous fashion quotes, it was Hardy Amies that said: “A man should look as if he has bought his clothes with intelligence, put them on with care, and then forgotten all about them.” Which is clearly what Wooster has done here. But unaware as he might be about the right way to fasten a double-breasted coat, he knows how to make it stand out, mainly by layering it on top of an all-black outfit that takes none of the shine away from it’s brilliance.

Nick Wooster's 15 Best Outfits

Jaywalking’s All-White

What do you do when you haven’t got time to make sure your clothes fit perfectly? Wear ones that look more like fashion house prototypes that finished off-the-peg pieces. As usual, Wooster has used a simple grandad collared shirt as a way of toning down a more zany piece, which this time comes in the form of a lightweight blazer covered in frays, pins and overhanging layers. Add some relaxed trousers and slip-on sneakers and you look like you’re (almost) ready to go.

Nick Wooster's 15 Best Outfits

Easy Does It

Wooster, is that you? We hardly recognised you in such a conventional look. Proving that not even Mr Fashion himself can resist the charms of a simple blouson jacket, here his look skews classic with contrast collar outerwear on top of wide pleated trousers and white sneakers. It’s a Scandi minimalist outfit that has all the elements of a highbrow fash-pack look, but one that could be easily replicated on the high street.

Nick Wooster's 15 Best Outfits

Needs More Buttons

If this is what Arctic explorers dress like in today’s world, sign us up to the next expedition. Proving that style standards needn’t slip in the winter months, Wooster once again proves he is the master of open layers. The raffish form of his long, pocket-laden coat plays well with the worker-style boots and robust woollen cardigan for a killer mountaineer at the fashion afterparty look.

Nick Wooster's 15 Best Outfits

The New Black Tie

It’s not a Wooster look at least it rips up the rulebook. Using all the constituent parts of a dinner suit, here the standard black tie look has been updated. There are some rules retained, mind – chiefly the satin, peak lapels and just the top button done up out of the pair available. The hems on the suit trousers are also slightly higher than on a traditional two-piece but longer than Wooster’s usual around the calf crop. However, it’s the white knitwear and shirt that really swerves the norm. And to end strong, high-shine black brogues worn sockless, and this time eyewear it’s permissible to wear indoors.

Nick Wooster's 15 Best Outfits

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