‘You may be interested in this,’ says Simon Holloway, pulling a tuxedo off a rail in a suite of The Carlyle hotel in New York. It looks a little worn, and I’m wondering whether this is some new ageing technique being applied by Dunhill’s creative director when he says, ‘This was Sinatra’s.’

Ol’ Blue Eyes wore a Dunhill tux, something Holloway discovered as he scoured the world for archive pieces at auction bearing the name of the British house he’d been hired by a year ago.

‘A worldly American in the last century would have recognised Dunhill as a well-known British maker of luxury,’ explains Holloway. And as if to reinforce the point, he whips out another black tux. ‘This was Truman Capote’s, the one he wore to the Black and White Ball.’

If you’re American, and/or have seen the series Feud: Capote vs. The Swans, you’ll know that this is the menswear equivalent of someone saying, ‘Here’s King Arthur’s sword Excalibur, you know, the one he pulled out of the stone.’ Capote’s famous masquerade of 1966, held in the Plaza Hotel’s Grand Ballroom, was a cause celebre. The society party to end all parties; the night in New York that showcased elegant eveningwear. For the host to be wearing Dunhill speaks volumes about the label’s historical luxury credentials.

It is those that Holloway has been ferreting out from wardrobe collections around the world, building up a library of vintage pieces from which to draw 21st-century inspiration. ‘One of the first things I did when I arrived at Dunhill a year ago was to buy back a lot of archival pieces. I bought a whole rack of clothes from one client who had impeccable taste,’ he reveals.

The result is his first full collection for the house, for autumn/winter 2024, now on sale, which pays homage to the elegant travelling Englishman who might wear a Prince of Wales check suit one day, and a pair of cashmere jeans with a short-sleeve, open-placket, fine-gauge wool knit the next. The trousers are usually fastened Gurkha style, with a wrap-around waistband, and the top-coats are soft, short and made from double-face wool, or longer and in Prince of Wales check or brown leather, or reversible in technical fabric backed by wool.

In terms of Dunhill eveningwear, Holloway is channelling the kind of thing Truman Capote or Frank Sinatra might have worn had they been released from the convention of black wool and satin lapels. Now the Dunhill man can indulge in tuxedos in dark navy wool, lustrous brown velvet or ecru barathea. Or go for, as Holloway puts it, ‘a full Duke of Windsor moment with a rust-coloured jacket and charcoal-check trousers’.

For Dunhill eveningwear is incredibly important, explains Holloway, reaching for a rack hung with glamorous pieces. ‘We have a reversible midnight- and navy-blue car coat; a double-breasted very, very fine wool-cashmere lounge suit in black with a larger reverse satin lapel, rather than just a tiny silk one; a natural indigo-dyed chambray shirt; a chocolate-brown Supima-cotton velvet double-breasted suit with matching overcoat; an all-ecru look in a barathea suit and coat – with a matching sneaker.’

And there are accessories to match: ‘There’s the full array of cummerbunds and quite voluptuous bow ties; beautiful waistcoats; a bib shirt; and velvet evening slippers.’ He points to a pair in midnight blue that has a vintage car embroidered on each shoe. ‘This is a depiction of a car that’s actually in our archive.’ It’s a Dunhill motor from the firm’s early years (it was founded in 1893), when it started as a maker of accessories for the first drivers. ‘Dating from about 1918, it’s in a garage in Luton as we don’t have anywhere to display it,’ says Holloway of the original. ‘But we’ll get it out at some point.’

There are other “mascots”, too, he says, all found in the firm’s archive, including three dogs: bulldog, greyhound and terrier. ‘We’ve put them on the slippers to create some conversational elements, and it’s kind of nice to have a little ironic sort of twist to what are otherwise quite serious evening clothes.’

One thing’s for sure, Dunhill eveningwear is no longer confined to the conventional.

dunhill.com