You know Dermot. We all know Dermot. The presenter has fronted more prime time television shows than we can shake a neatly tailored suit at — and he’s got his fair share of those, too. In fact, every time O’Leary steps his well-practiced, well-polished shoes onto a stage — microphone masterfully in hand — we find ourselves wondering just where he got that particular waistcoat from, or those cufflinks, or that tie bar…
So what better time than lockdown to get the low-down on O’Leary’s wardrobe? And who better to show us his style than the man himself? Because it really is quite the wardrobe. We’re talking countless plastic-shrouded suit jackets, a waterfall of textured ties and a stockpile of shoes that would make even the most prolific collector blush.
So, without further ado, let’s pass over to O’Leary himself to talk you through his favourite outfits and accessories. Photographed in his London home by his wife, The Crown director Dee Koppang O’Leary, here’s the ultimate guide to dressing like Dermot.
Orlebar Brown 007 Navy Piped Towelling Jacket
“This is a great summer staple for me — from one of the best British summer brands. I have way too many of their swim shorts. But Orlebar Brown’s blue towelling top with white piping goes equally well with a pair of shorts in the summer as it does with dark jeans when the sun goes down.”
Private White V.C The Revere Field Jacket
“Private White, Victoria Cross are a label who started in Manchester — and still manufacture there. Founded by James Eden, I can’t recommend them enough. Their coats are things of beauty and I have an obsession with their macs — but my favourite right now is this Revere Field Jacket in olive, which is equally at home in the city as it is at a festival.
“The story of the company is also really touching — really inspiring. I love that whole heritage of British fashion. And James Eden has recently put his factory’s efforts into making PPE for the NHS. I couldn’t love them more.”
John Smedley Lorca Short Sleeve T-Shirt and Incotex Trousers
“Smedley are one of the heritage brands. I adore their knitwear and the new Lorca is a really lovely T-shirt that you can wear smartly. Incotex are part of the Slowear brand, who do marvellous one-stop capsule wardrobe style collections. Both make really beautifully made, ready-to-wear pieces. And you can also see here my beloved crucifix — given to me as a 40th birthday present by my wife Dee.”
TAG Heuer Carrera with NATO strap
“I like to wear watches as part of my outfits, not just as accessories. As such, I don’t always wear one. I’m also not a massive fan of big watches — I think they’re too showy. But this, the TAG Heuer Carrera, is just the right size and weight. I much prefer the editions with the Heuer badge on them — they’re much more old school. And I really love the NATO strap, it gives it a summer feel.”
Thom Sweeney Suit, Turnbull and Asser Shirt and Drake’s Tie
“I love wearing a suit, and this is pretty much my A-Team. I’ve been wearing Thom Sweeney for years now — Luke and Thom are friends and they really do make a suit that you’ll be wearing for the rest of your life. It’s a proper heritage, legacy investment.”
“Drake’s are the daddy when it comes to ties (they also do a mean chunky knit) and ditto with George Cleverly when it comes to shoes. Turnbull & Asser do a bespoke shirt service that is second-to-none; you feel like a cross between Bond and an — albeit minor — Royal when you visit their shop. I also look to Emma Willis for shirts.”
Sunspel Off-White Sweater and P. Johnson Blue Trousers
“Sunspel are another of my favourite British brands. Their sweats and T-shirts, in particular, are both stylish and wearable. They’re also nice to wear with a smarter trouser. I also love a pleat, and P. Johnson are an Australian tailor with an Italian influence — specialising in really well-cut bespoke trousers as well as suits. I’d wear this outfit with some Church’s Desert Boots.”
George Cleverly Suede Penny Loafers
“As mentioned above, George Cleverly shoes are, once again, a proper long-term heritage investment. And they’re more than worth it. You really will be wearing these shoes for the rest of your life. I’ve picked a pair of suede penny loafers as my favourites, but I’m lucky enough to have a few pairs of theirs.
“If you’re in the market for a pair, you should visit the store. They have a small shop on the Royal Arcade just off Bond Street and, if you’re lucky, you’ll get the chance to meet Mr. George Glasgow Snr — one of the owners and chairman, and a true character of British fashion. He even featured, in a small cameo, in Phantom Thread. And if he’s good enough for Daniel Day-Lewis…”
Want more advice from style icons? Here’s Alessandro Squarzi’s guide to summer style…
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