The holy grail of a perfect wardrobe is no longer the vertiginous heel. It’s the shoe that you can slip on at 8am, survives a full day of meetings, errands and detours – and still feels comfortable when your step count tips into five figures.
Celebrity stylist Deborah Sheridan-Taylor believes the secret is accepting that practicality and style no longer sit at opposite ends of the wardrobe.
“Comfort doesn’t have to mean compromise,” she says, “but you do have to be mindful.”
The trending styles that actually deliver on comfort
One of Sheridan-Taylor’s favourite styles this season is the “glove” shoe. Sleek and sculpted, these flats are the latest evolution of the ubiquitous ballet pump trend.
“It’s designed to hug the foot in a barely-there manner,” she says and is perfect for busy days when you want something slightly more elevated than a slim trainer.
Sheridan-Taylor suggests pairing it with pleated-front tailoring, like pressed jeans or seamed trousers. “Whether you’re rushing from the Tube station or wandering around a gallery, you’ll appreciate the glove-like foothold.”
If you need extra support, she also recommends adding gel inserts at the ball of the foot, as “that extra cushioning makes all the difference on long days”.
Uniqlo Square Flat Shoes, £34.90
When rain is on the forecast
British weather demands practical footwear. Sheridan-Taylor says she advises her clients to think in terms of “commuter shoes”.
“Not Melanie Griffith in white Reeboks,” she laughs citing [iconic Eighties film] Working Girl, “but let’s be realistic – sometimes you need a spare pair to change into.”
For genuinely wet days, she makes a case for the wellington boot. “Call me crazy, but wellies really work.”
At the luxury end, she points to rubber styles from Céline that have made their way onto the runway. Meanwhile, brands such as Tretorn have been able to transform rubber into something slightly smarter than farming gear.
A sleek black or deep brown rain boot can sit comfortably alongside tailoring.
“I love a wide-leg trouser nonchalantly tucked into the top of the boot,” she says.
If wearing boots with a skirt, she suggests adding ultra-sheer tights – around seven denier – to create what she calls an “aristocratic chic” effect, which is “far more 2026 than countryside cliché.”
M&S Brown Wellies, £36
Making practical shoes look stylish
Trainers, loafers and Derby shoes can easily tip into purely practical gear. The difference, Sheridan-Taylor argues, lies in styling.
“I start every outfit with a shoe, the shoe dictates everything,” she says.
Rather than defaulting to predictable workwear combinations like suit trousers and trainers, she suggests leaning into something more preppy, like lace-up Derbys paired with a long A-line dress, a chunky knit and leather blazer.
Heeled loafers can also bridge the gap between comfort and sophistication. Sheridan-Taylor says all you need is a two-inch heel to elevate your look into something more sophisticated.
Worn with a leather pencil skirt and Argyle tights (another autumn/winter trend), loafers feel cool as opposed to utilitarian.
& Other Stories Leather Derby Shoes, £139
Cos Animal-Print Pony-Hair Effect Leather Loafers, £119
Trainers that don’t look like you’re heading to the gym
In what Sheridan-Taylor calls our “post-Sambas era”, trainers have become even slimmer, blurring the line between sports shoe and ballet flat.
She highlights the rise of the “sneakerina” – a hybrid between sneaker and ballerina pump, which is an easy way to up your trainer collection.
Colour and finish also play a big role. “Bright red, lilac suede or stark white can steer a sporty shoe into something more fashionable,” she explains.
She references the red patent trainers seen at Dries Van Noten’s spring/summer 2026 show as an example of how bold colour can change the whole vibe of a shoe.
As for styling, “trainers [work best with] stark contrast,” she says. Fluid midi skirts with a long trench coat, or oversized trousers with a simple T-shirt and suede bomber, help blur the line between sporty and styled.”
Puma Speedcat Ballet Metallic Shoes, £70
Boden Delphine Slim Sole Trainers, £79.20 (were £99)