The debonair and well-connected co-founder of online auction house Paddle8 walks us through the art of dressing tastefully.

Forget Thor, there’s a new hammer-wielding superhero in town. When you need to raise some serious funds at a charity auction, you call in the debonair Mr Alexander Gilkes to make it rain. The night before this interview, Mr Gilkes, 36, had hosted a New York Fashion Week charity auction for amfAR, attended by Messrs Leonardo DiCaprio, Robert De Niro, Jay Z and guest of honour Mr Harvey Weinstein, which raised more than $2m for Aids research. Two weeks later, he was jetting to Hollywood to host Sir Elton John’s star-studded Oscar-viewing-party auction, where he helped raise $6.2m for the singer’s Aids Foundation.

By day, Mr Gilkes is co-founder of Paddle8, an innovative online auction site that has blown the dust off selling art in the digital age. Having worked as chief auctioneer for Phillips, one of the world’s biggest auction houses, where he sold “$45m Rothkos and Warhols for telephone-number sums”, Mr Gilkes realised there was a gap at the other end of the art market. “The bricks-and-mortar auction world is riddled with inefficiencies,” he says. “It’s very cost prohibitive and it’s an arduous process.” So he and his partners decided to create a nimble, high-end eBay for selling art and collectibles. They launched Paddle8 in 2011. The website deals mainly in the $1,000 to $100,000 range, selling the work of hot contemporary artists as well as more affordable “editions” from big names such as Ms Tracey Emin and Mr Damien Hirst. It’s been a roaring success. While the company is coy about discussing profits, it is growing fast and now employs more than 100 people with offices in New York, LA and London.

Named on Vanity Fair’s International Best-Dressed list, Mr Gilkes’ approach to his wardrobe is similarly savvy, pairing design classics with more contemporary updates. The all-auction man invited MR PORTER to shadow him for a week around his Manhattan haunts.

This is me in my Greenwich Village apartment. I used to be a hoarder, but I’ve learnt to buy fewer, but better, pieces. This is what I typically wear to work at Paddle8, a 10-minute walk away in the East Village. A shawl-neck cardigan and chinos are smart enough for internal meetings, but extremely comfortable and utilitarian. When you live Downtown, you become a little less formal. Uptown is more formal – any meeting above 35th Street probably requires a suit.

Mine is a relationships-based business and typically I will be out in the evenings at an event at a gallery or an art book store such as this one, which is called Printed Matter. This is the sort of outfit I wear out and about. I find double-breasted blazers very flattering – or a signature one-a-half-breasted in the case of Brunello Cucinelli.

Here, I’m at David Zwirner’s gallery in Chelsea. He’s one of the most admired gallerists in the world right now and I’m privileged to have him as an investor in Paddle8. I love the camel colour of this Hardy Amies double-breasted blazer and the Charvet lapel pin. And it’s always useful to have a smart Berluti case to conceal my scruffy notes.

A Mackintosh is a classic staple in any Brit’s wardrobe and I pretty much live in Common Projects sneakers. Sant Ambroeus in SoHo is a regular haunt, whether picking up a coffee if I’m walking Thatcher, my four-year-old cavapoo (a cavalier King Charles spaniel crossed with a poodle), or meeting someone for lunch. Sant Ambroeus has invited Paddle8 to contribute to its famous plate wall, which is an honour.

I hold a lot of meetings here at Hôtel Americano, which is a quiet little spot in New York’s gallery district in Chelsea. I like its mid-century design. When I travel, I tend to wear J.Crew chinos. They’re extremely comfortable and I have them in every colour. For expediency, I try to stick to hand luggage – a suit carrier and a small Globe-Trotter suitcase.