It's often said that fashion is a young man's game. Who else could be bothered to balance on its ever-shifting edge?
Nickelson Wooster, for one. The 55-year-old fashion director has become a social media sensation with his sharp, seemingly effortless sense of style. Wooster freelances as a creative consultant for various brands and designers, and is a favourite of street style photographers at events such as biannual menswear trade fair Pitti Uomo in Florence.
He's not alone - 'best dressed' lists are now filled with well-seasoned gents. Other members of the 40+ style set include The Sartorialist blogger and photographer Scott Schuman (47); Spanish football coach Pep Guardiola (44); actor Jude Law (42). Then, of course, there's Tom Ford – a man so stylish at 53, he can make double denim look good.
The secret to their success is simple, but not easily acquired. They know what clothes work for them and use details to accent an overall look - forget slavishly following fads practiced by younger so-called fashionistas.
Been around the block
Neale Whitaker says this ability to edit a look is his greatest style asset. Known for his role as resident judge on Channel Nine's The Block and current Editor in Chief for Vogue Living, Whitaker was recently named one of Australia's best dressed men for 2014.
The 52-year-old has always been a fan of fashion, but early involvement in the industry allowed him to take a step back from the revolving cycle of trends.
"I've always retained a healthy cynicism towards the fashion world," he explains.
"I love it, but I am not of it. Mostly because of its transience and its excesses."
His career began working for infamous UK fashion PR guru Lynne Franks (the inspiration for Absolutely Fabulous's Edina Monsoon) and as a publicist for high-end London department store Browns.
Whitaker's signature look is surprisingly understated and a testament to the classic, rather than the cutting edge. Double-breasted jackets are accented with a pocket square or tie, while white pants and R.M. Williams boots provide a sharp, yet casual aesthetic.
"I'm not particularly into suits," he explains. "I've got about half a dozen but I rarely wear them. I do the thing that you're not supposed to do – I break them up and wear them as separate pieces."
Another man putting younger lads to shame is Sydney-based restaurateur Maurice Terzini.
The 50-year-old is responsible for Bondi's iconic Icebergs Bar and Dining as well as Da Orazio Pizza + Porchetta and guerrilla-clothing label Ten Pieces.
"It's important to be inspired by trends, but also to develop your own style," he explains.
"Fashion should be ageless. Yohji Yamamoto is still one of the coolest men alive at the age of 70-plus."
A fan of avant garde designers such as Ann Demeulemeester, Rick Owens and Boris Bidjan Saberi, Terzini's style errs on the artistic side. Loose, layered pieces in asymmetrical cuts are teamed with the latest designer sneakers to create an edgy, relaxed look.
"My basic rules are: simplicity with great detail, and items that make me look good.
"I do know that the older I get, the more and more I just want a uniform that is adaptable to any occasion, from dinner to a weekend at home to a night out on the town.
"Also, I have never really been a fan of too many colours, and a great pair of shoes or sneakers are essential."
While the fashion industry remains obsessed with draping its latest creations on young shoulders, it's inspiring to see men such as Wooster, Whitaker and Terzini proving that a true sense of style only comes with age and self-awareness.
"You do wake up one morning where you've reached a certain age and you're evaluating yourself, your age and your appearance," says Whitaker. "But there was no way that I was going to conform to anyone's rules."