Grandpa knows best (dressed): Good tailoring is passed from one generation to the next

When my grandfather, Athol, died during my twenties, I inherited a few of his things: a delicate gold ring, a polka-dot silk scarf, the mid-century dining table I’m sitting at to write this article and an evening suit. Judging from the flared trousers and wide, brocade-trimmed lapels, I imagine he bought this sometime in the 1970s for nights out with my grandmother. Although I do not know the exact date of purchase, I do know the location from the Saunderson label inside it.

My mother tells me that this now long-closed clothing store, on Abington Square in Northampton (where my family hails from), was a pretty chi-chi establishment back in the day. This feels correct, considering the suit I inherited was not only incredibly on-trend for the era, but came with a blowsy velvet bow tie and cummerbund from Harrods. My grandfather was a man of exquisite taste.

When it comes to the style of the suit, it’s something I would happily wear today. The only problem is it doesn’t fit. Although our sense of style and love of menswear were aligned, our proportions, sadly, were not. I am taller and stockier, but also less broad than him, meaning the suit is both too large and too small depending on where your eyes land. Sadly, to make it fit me, the suit would require the kind of insurmountable alterations that are greater than mere tailor’s tweaks. Thus it hangs in my wardrobe, unable to be worn, but forever providing me with a sartorial thread back to grandpa.

The idea of inheritance isn’t only in the physical. Some are lucky enough to come into the possession of clothing from well-dressed relatives that they can wear, repurpose, repair and love for many years. For others, like myself, that connection might be more temporal: a way of thinking about the way they dress that they might have absorbed from an elder they admire or that they hope to pass down to their children. Read on to meet the men and women who, in every sense of the phrase, embody inherited style.

Rupert and George Ponsonby

Rupert and George Ponsonby are a father and son who share more than mere DNA — they share a wardrobe of exquisite tailoring passed down from maritime magnate Sir Nicholas Cayzer, the grandfather of Rupert’s wife, Amanda. ‘He was someone who liked things done in a proper, old-fashioned way and he liked good lines: good lines with his ships and good lines with his clothes,’ says Ponsonby Snr. ‘He wasn’t a showman.’

When Sir Nicholas (Baron Cayzer from 1982) died in 1999, he left behind a bespoke archive shaped by his life: grey double-breasted formal suits worn in the City, lightweight sandy-coloured silk-mix suits worn on business trips in South Africa and shooting tweeds with plus-fours worn during his downtime, mostly from the 1960s and 1970s and cut by tailoring house Anderson & Sheppard.

Even better than inheriting all of these pieces is that none of them have needed altering for either man — forgiving the occasional tweak. ‘I’ve always been someone happy to wear braces,’ says the younger Ponsonby, who works at London antique and reproduction studio, Jamb, ‘so if there’s ever been a slightly wider waist on a pair of trousers, that’s never been an issue.

Although they might wear the same suits, the way they wear them differs. Son thinks father is far braver than him, referencing a pair of yellow dungarees to which he’s particularly partial. ‘I like a cacophony of materials and colours,’ says the senior Ponsonby, ‘and I like to be nice to my ankles by wearing bright socks, to show them I respect them.’

Father takes pleasure in customising Lord Cayzer’s suits with colourful accessories. Son, instead, tends to go in a different direction. ‘I try to lean into it, rather than make them my own,’ he explains. ‘I have such an enjoyment of the past that it would feel wrong to reinterpret them. Instead, I enjoy trying almost to embody my ancestors.’

Whichever way they’re worn, one thing’s for sure: the pieces themselves have stood the test of time. ‘If I wear one of the grey three-piece suits in London for an event, people will literally come up to me and say: “That’s the most beautifully cut suit,”’ says the senior Ponsonby, chuckling. ‘The joke is, it wasn’t actually cut for me: it was cut for my grandfather-in-law!’

Sam Chatto

Ceramicist Sam Chatto, a grandson of the late Lord Snowdon (one of the most stylish men of the 20th century) recently commissioned his first bespoke suit from tailor Fedro Gaudenzi, whose studio is on Cork Street — a stone’s throw from Savile Row.

Double-breasted with white buttons and wide lapels, the suit is cut from a vibrant blue velvet. As a man who finds himself rushing between the studio and social engagements, Chatto wanted this suit to serve him well for both occasions. To that end, the jacket has been specifically designed for his posture as he throws clay with all manner of hooks and pockets inside to hold his artist’s tools, as well as sleeves that can be easily rolled back.

In part, this was inspired by early-20th-century ceramicists Shōji Hamada and Bernard Leech. ‘They would wear suits to throw in and part of it was this incredible statement: we can throw work so impeccably that we won’t get a spot of clay on our clothes,’ the ceramicist says.

The decision to use a cotton velvet woven in a pin needlecord—a sturdy fabric that alludes to French denim workwear — recalls the style espoused by 19th-century actress Sarah Bernhardt, who wore velvet suits that could take her from the stage to glittering Belle Époque salons without needing to change.

'Part of the idea was also that this suit will pick up a certain amount of wear over the years, so it will end up with a kind of patina,’ says Chatto of his preference for velvet. ‘I like the idea that the suit will eventually carry that kind of imprint of how it’s been used.’

The scion comes from a distinguished line of artists: his mother, Sarah Armstrong-Jones, is a painter and his grandfather one of the 20th century’s most influential photographers. The two share a penchant for blue.

‘He had his own style of blue shirt that he’d always wear or have his sitters wear,’ Chatto explains. ‘There is something quite creative about the shade it was, a kind of Yves Klein mid-blue. It has a certain resonance and projects nicely. It has a strength to it without being a dominating colour.’ Artistically, it is a shade that inspires him as much as it did his grandfather. ‘It’s a beautiful colour that works well with white,’ the artist notes. ‘In my own context, I’m combining it with white porcelain and the glazes I use are blue. There is a nice symmetry when you consider [Lord Snowdon] tended to use blue shirts against a white or dusty backdrop.’ Subtle shades of his grandfather’s legacy abound in this original suit.

Brunello, Camilla and Carolina Cucinelli

‘I wouldn’t say my sense of style came from the family, because we were farmers,’ says Italian fashion designer Brunello Cucinelli. ‘Instead, I drew a lot of inspiration from the British, starting with Edward VIII.’

Menswear fans will be familiar with Cucinelli’s eponymous label of luxurious, laid-back tailoring, which is created and manufactured in Solo-meo, a picturesque medieval village in Umbria that serves as the brand’s headquarters.

As the well-dressed leader of a fashion empire, it is perhaps unsurprising that his sense of style descends from suiting royalty. He’s also a fan of The King’s approach to style. ‘The way he might wear the very same coat for 20 years or so — that’s something I do, too.’

Although his aesthetic sensibility might not come from his ancestors, the way he approaches fashion certainly is. ‘I come from a farming culture and on a farm you don’t throw anything away,’ Cucinelli explains, standing up from behind his desk to demonstrate that he’s wearing a pair of light-blue jeans that are 12 years old. ‘That’s why I don’t like to waste things.’

This isn’t an empty boast. Mr Cucinelli assures me that he keeps and stores every garment that he’s worn throughout his life, creating a considerable sartorial inheritance for his daughters, Camilla and Carolina, who today work alongside him at the brand — and who both regularly dip into the archive and repurpose their father’s clothes for their own wardrobes.

The three, he says, are relatively aligned in their sense of style — and his daughters regularly influence his way of thinking. ‘I draw inspiration from the way they use colour,’ Cucinelli beams. As many children do, they have challenged his preconceptions. Carolina loves black; ‘I’ve never worn black in my life,’ he laughs.

Cucinelli’s inheritance extends beyond his family. By his own admission, no person has had such an impact on his sense of style than a certain American designer. ‘My great teacher, the person I’m most inspired by, is Ralph Lauren. Not so much for the shape, the cut or the colours, but for the way he combined pieces together. Four years ago, I went to New York to thank him in person for all the inspiration he’d given me.’ A spiritual style godfather, perhaps? ‘Definitely,’ he muses.

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This feature originally appeared in the November 4, 2026, issue of Country Life. Click here for more information on how to subscribe.