Style tips from CEOs – from Instagram’s Mr Kevin Systrom to Google’s Mr Sundar Pichai.

Mr Kim Jong-Un, known for his usual uniform of black Chairman Mao suits, recently made headlines for putting on a grey suit and horn-rimmed specs for his annual New Year television address. Apparently, it was an effort to appear more palatable and friendly to the West, and it seemed to work, with The New York Times branding him “dapper”. Still, we couldn’t help thinking that, sartorially speaking at least, Mr Kim had missed an opportunity to push the envelope a little further at work. Today, dressing for success isn’t about suits – it’s about being adventurous.

A quick look at the sea of sweaters sported by the frustratingly successful millennials in Forbes’ 30 Under 30 Europe list shows how times are changing. Dressing smart and being successful, at least in the traditional sense, are no longer necessarily related. This doesn’t mean that suits have been sacked, but the lines for what passes as acceptable workwear are increasingly blurred. With that in mind, how on earth do we define what it means to dress impressively to work?

A good place to start might be California. The Golden State has a long history of messing with workwear dress codes, and was responsible for introducing the Casual Friday concept to the world after appropriating it from a 1960s Hawaiian initiative known as “Aloha Friday” (an excuse to wear a bright, camp-collared shirt). By the 1990s, it had spread across the world, permitting millions of men to start wearing loafers with boot-cut jeans and generally dressing like they were about to present Top Gear.

Today, things have become more refined, if a little complex. In the wake of Messrs Bill Gates, Steve Jobs and Mark Zuckerberg, Silicon Valley is now home to an echelon of tech entrepreneurs who exude a kind of self-assured nonchalance with their clothing. It’s evolved past the cliché of Mr Zuckerberg’s stodgy hoodies, and it now looks something like a rollneck under a blazer, a shirt under a cardigan, or a crisp white T-shirt under a navy bomber jacket. Current proponents of this look include Mr Evan Spiegel, co-founder of Snapchat, who wears everything from open-necked shirts under a jacket to streetwear sweaters from Acne Studios, and founder of Oracle Mr Larry Ellison (the eighth-wealthiest man in the world as of this month) who alternates between black mock necks under suit jackets or a simple cashmere V-neck. Instagram founder Mr Kevin Systrom and Google CEO Mr Sundar Pichai are both partial to a pair of Lanvin sneakers, as well as cardigans. It should be noted that these men do still wear formal suits occasionally, but they can enjoy the pleasure of smartening up as and when (and if) it takes them.

Of course, these gents are senior figures in extremely innovative and influential companies. What, for instance, does the man who wants to impress in a less-than-creative office wear to work? And what about the guy who works at an edgy media company but wants to smarten things up? We’ve compiled a few helpful tips on this below. Dress for the job you want, as they say…

RELAX YOUR TAILORING

If you were looking for a way to strike the perfect balance between smart and casual, you’ll find it with Noah. The New York-based label founded by Mr Brendon Babenzien launched on MR PORTER late last year, and mixes tailoring and basics that are inspired by surfer culture (think pared-back blazers layered over sweaters and rugby tees). The brand is known for marrying a streetwear attitude with a tailoring sensibility, and provides a safely elegant alternative to a full suit.

BE SMART WITH YOUR SNEAKERS

The heritage shoemaker John Lobb has also caught the smart-casual bug, and now makes a range of smart sneakers that will pair reliably with casualwear as well as with tailoring. Lanvin also do a fine pair. Wear them to kick your start-up attire into shape or to add a little edge to a suited look.

MAKE IT CASHMERE

Cashmere is a way to immediately boost your style status at work. Brunello Cucinelli in particular is a name that comes up a lot when researching what the Silicon Valley set wear – Mr Zuckerberg reportedly has his grey T-shirts bespoke-made by the Italian brand, and Mr Systrom has a taste for its sweaters. Cashmere sweaters like these two, from Brunello Cucinelli and Hardy Amies respectively, will work nicely under a suit jacket, but can also be worn on their own.

COP A ROLLNECK

You can thank the late Mr Steve Jobs for this one, not to mention the host of fashion designers and street-style icons who have brought it to fashion’s frontlines in recent years. Try one from John Smedley, and wear it under a blazer to emulate the aforementioned Mr Ellison – this black worsted wool one from Mr P. is a good shout.

BE A POST-IRONIC NEO-CEO

For the CEO of the future, there’s nothing for it but workwear that’s inspired by streetwear. Or is that streetwear inspired by workwear? In any case, this sartorial inception is best illustrated by MR PORTER’s exclusive capsule collection from Balenciaga. Throw one of the brand’s lanyards over this Vetements tee, which has been appropriately emblazoned with the word “staff”. A start-up investor’s dream.