Welcome to the season of the Posh Grandpa, fashion’s newest main character. We’ve had Brat, we did Coastal Grandma, we loved Tomato Girl Summer. The world is pretty heavy right now, as you’ll have noticed, so any opportunity to lighten up is precious. The nonsense is the point.
Character dressing is style that makes you smile, but it’s not just that. There is infinitely more joy in these looks, however silly they are, than there is in aspiring to look rich and pretty, which is where the aesthetic centre of gravity of our culture swings back to again and again. The esoteric sides of fashion’s personality capture something important about style, which is that it needs a bit of friction to make it interesting. The pebble in the boot, the surprise to snag the eye. This is where the magic happens.
I am all in with Posh Grandpa dressing, and not just for the lols, although I am also very much enjoying the spectacularly ridiculous vibe name. This is exactly how I want to dress most of the time. Slip-on shoes? Check. Comfy trousers? Copy that. Henley button-ups, or maybe a sensible quarter-zip? All over it.
Taking inspiration from menswear is the oldest trick in the chic woman’s playbook, but if streetwear was about dressing like an adolescent boy and normcore was a nod to the dads, Posh Grandpa is retro and refined.
If you want to know where fashion is going next, the best place to look is not the catwalk but vintage stores and car boot sales. Vintage shoppers are the most fashion-forward demographic, so what they are wearing now you’ll be wearing in a year or so. The look is Harry Styles, A$AP Rocky and David Hockney. It is Timothée Chalamet in Marty Supreme and Cillian Murphy in Peaky Blinders. It is Alexa Chung in a perfect navy crewneck sweater, and Bella Freud in a trouser suit.
This look is mellow but never dull. Muted colours and classic cuts are undercut by a sly sense of humour. You can play it straight, all soft tailoring and thoughtful layering, or you can lean into the eccentricity. For evening, instead of the usual tropes of glamour – sparkle, skin – embrace camp and drama. Velvet trousers with a silky shirt. Possibly a smoking jacket? Keep the jewellery minimal, the hair simple: we want louche glamour not Dynasty power dressing.
But start, always, from the ground up. The right shoes will do a lot of the heavy lifting. Tasselled loafers are encouraged, as is shoe polish. If loafers feel too obvious, consider a slim lace-up jazz shoe. A velvet slipper, if you are feeling bold. From there, the silhouette builds itself quite naturally.
Trousers, crucially, not jeans. Denim is a little too blunt an instrument here, because you want something with drape: pleated fronts, a slightly higher waist, a leg that falls cleanly rather than clings. There is something marvellously liberating about a trouser that isn’t trying to be sexy. A Henley instead of a white T-shirt is a good starting point for layers on top – faintly old-timey, but also very modern-utility, especially under an overshirt. Or layer a shirt under a cardigan or a quarter-zip.
And then (this bit is important) you need to interrupt it with something modern that jolts the eye. A leather jacket thrown over the top is perfect to stop things from veering into pastiche. Or something as simple as a contemporary belt or a pair of angular sunglasses can shift the balance.
Beneath the tongue-in-cheek name and the nostalgic references, the Posh Grandpa trend speaks to a desire for comfort but also character. In a fashion landscape that can feel relentlessly polished, there is romance in a look that finds beauty in the slightly off-kilter. Instead of a fantasy of youth or wealth, it is an allure that leans on less obvious signifiers. Impeccable taste, a favourite armchair and great shoes? A life well-lived is always a good look.
Model: Fu at Milk Management. Hair and makeup: Delilah Blakeney using Hair by Sam McKnight and Charlotte Tilbury Styling assistant: Charlotte Gornall. Jacket, £69.99, Zara. Jumper, £49.99, John Lewis. Shirt, £29.90, Uniqlo. Trousers, £29.99, Zara. Shoes, £165, by Camper from Schuh. Chair, £199, John Lewis
