Unconventional men’s tailoring to make an impression this winter

This winter’s men’s tailoring is defined by razor-sharp reinterpretations of classic silhouettes, designed to make you stand out over a celebratory season ahead

Men’s Tailoring 2023 Fashion Story
Left, jacket, £2,330; jumper, £810; shirt, £590; tie, £320; trousers, £990, all by Bottega Veneta. Right, jacket, £2,500; top, £510; trousers, £1,150; boots, £1,650, all by Gucci. ‘Tape’ armchair, from £4,340, by Nendo, for Minotti
(Image credit: Photography by Daniel Riera, fashion David St John James)

Sculpted silhouettes, warped weaves, razor-sharp cuts – men’s tailoring is imbued with a spirit of subversion this season, as designers and brands seek to rework and reimagine the suit. Their spoils arrive at the beginning of a season filled with potential for dressing up; here, as taken from the December 2023 Entertaining Issue of Wallpaper* – photographed by Daniel Riera Fashion with fashion by David St John – a selection of that tailoring ready to make an impression over the celebratory winter months ahead.

Razor-sharp men’s tailoring to make an impression this winter

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £1,650; top, £610; trousers, £1,150; shoes, £1,050, all by Fendi

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Take the unexpected proportions of Gucci’s elongated double-breasted blazer and wide-legged tailored shorts (top left), a playful top-heavy silhouette nonetheless conjuring the Italian elegance at the heart of the label. Or from Fendi, an immaculate single-breasted suit whereby the trousers are overlaid with a diaphanous apron-like skirt (below); when it was first shown in Milan, creative director Silvia Venturini Fendi said she was inspired by the outré dress codes of infamous New York nightspot Studio 54. 

Others riff on classic tailoring archetypes, like Dolce & Gabbana’s take on the white tuxedo – here cut with a narrow sculpted waist – or the shrunken two-tone lapel of a double-breasted suit by Maximillian Davis at Ferragamo which recalls military uniforms, here reimagined with a minimal rigour. 

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,550; trousers, £1,050; boots, £1,175, all by Alexander McQueen

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,550; trousers, £1,050; boots, £1,175, all by Alexander McQueen

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £4,100; shirt, £900; trousers, £800, all by Hermès. Shoes, £1,115, by John Lobb

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,600; sleeves, £1,100; top, £1,450; trousers, £1,300, all by Dior. Shoes, €850, by Santoni. ‘Fynn’ armchair, from £4,890, by GamFratesi, for Minotti

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket; trousers; gloves; shoes, all price on request, by Dolce & Gabbana

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket; trousers; gloves; shoes, all price on request, by Dolce & Gabbana

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,825; shirt, £240; trousers, £1,505, all by Ferragamo

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,590; top, £1,605; trousers, £965; shoes £1,290, all by Saint Laurent by Anthony Vaccarello

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Men’s Tailoring 2023 Fashion Trend Story

Jacket, £2,720; trousers, £1,030, both by Louis Vuitton. Shoes, £1,115, by John Lobb ‘CH88T’ chair, £491, by Hans J Wegner, for Carl Hansen & Søn

(Image credit: Photography by Daniel Riera, fashion by David St John James)

Model: Przemek Szubert at Riches Mgm. Casting: Ikki Casting at The Art Board. Grooming: Chris Sweeney at One Represents using Hair Rituel by Sisley. Digi tech: Marc de Miguel. Fashion assistant: Molly Swatman. Retouching: La Cápsula Fotográfica. 

A version of this story appeared in the December 2023 Entertaining Issue of Wallpaper*, available in print from 9 November, on the Wallpaper* app on Apple iOS, and to subscribers of Apple News +. Subscribe to Wallpaper* today!

Fashion Features Editor

Jack Moss is the Fashion Features Editor at Wallpaper*, joining the team in 2022. Having previously been the digital features editor at AnOther and digital editor at 10 and 10 Men magazines, he has also contributed to titles including i-D, Dazed, 10 Magazine, Mr Porter’s The Journal and more, while also featuring in Dazed: 32 Years Confused: The Covers, published by Rizzoli. He is particularly interested in the moments when fashion intersects with other creative disciplines – notably art and design – as well as championing a new generation of international talent and reporting from international fashion weeks. Across his career, he has interviewed the fashion industry’s leading figures, including Rick Owens, Pieter Mulier, Jonathan Anderson, Grace Wales Bonner, Christian Lacroix, Kate Moss and Manolo Blahnik.