Milan Fashion Week Men’s S/S 2019 Editor’s Picks
From footwear expert Santoni’s confectionary cabinet presentation, to Glenn Marten’s debut for Diesel Red Tag, we present the Wallpaper* pick of Milan Fashion Week Men’s S/S 2019

Giuseppe Zanotti: The Italian footwear aficionado presented a collection of clashing footwear styles for S/S 2019. Standouts included a new modular sneaker that can be customised by the wearer with interchangeable slogan Velcro patches, and a series of white leather tennis shoes covered in vivid paint splashes. Elsewhere, flyknit high tops came with heavy moulded soles and skater slip-ons in faded denim.
Church’s: Stepping out at Church’s this season is an update of the brand’s classic ‘Shannon’ style, this time appearing as a monk shoe in ink blue leather with a bold silver buckle side fastening. Elsewhere, the cobbler revisited its ‘Shanghai’ shoe by adding canvas panels alongside introducing a boot style in two tone aged leather. The brand’s signature ’Pembrey’ penny loafer gets ready for the summer sun in super soft suede.
Diesel Red Tag: Diesel Reg Tag recruited Y/Project designer Glenn Martens for its second season (its first was launched by Hood by Air’s Shayne Oliver). Martens presented a cool and confident collection of manipulated separates. Trousers came with ultra high waistbands and super slouchy leg lengths (a Y/Project staple), while jackets and blazers appeared warpped with draped panels and screw weft fastenings. Denim was key, but offset with more traditional tailoring fabrics for a ‘formal-meets-street’ feel. The accompanying collection lookbook was photographed by conceptual artist Hans Eijkelboom, featuring a diverse group of street cast individuals.
Jimmy Choo: creative director Sandra Choi explored new technological advancements in materials and manufacturing in a collection of ultra-light styles for summer. Japanese inspired whipstitching, machine-knitted uppers and a resin-dipped effect were some of the techniques used to striking result. Standouts included the brand’s signature skater sneaker being given a luxury upgrade in crocodile, and deck shoes with fold-down back to be worn as a slider.
Ralph Lauren Purple Label: The label took to the seas in a nautical inspired collection for S/S 2019. Seafaring tropes were updated in technical fabrications – a classic Harrington emblazoned with a graphic boating motif came in water resistant laminated cotton, while a lightweight windcheater was reimagined in gold metallic ripstop with tapped seams. This season also sees the introduction of the ‘The Ralph Suit’, inspired directly by the designer’s personal take on tailoring – a broad shouldered double-breasted jacket with neat waistline fastening at the bottom button.
Santoni: The Italian footwear label held its S/S 2019 presentation at a traditional Italian cafe in the heart of Milan. Guests were invited to enjoy ice cream as shoes from the collection were humourlessly presented within glass confectionary cabinets and served up on trays by waiters. The brands classic single and double strap monk shoes appeared in the softest leather, while their heels and soles were left untreated to keep in line with a more minimalist mood. Elsewhere, the pared-back direction continued with unstructured suede desert boots with eliminated seems, and elegant loafers in refined exotic skins.
Kiton: Alongside showcasing a collection that focused on relaxed lightweight suiting, Neapolitan tailoring brand Kiton continued to push the possibilities of fabric development with their ’KTN’ collection. Designed by twin brothers Mariano and Walter De Matteis, the collection is made from a super fine yet strong cotton yarn created by Kiton at the brand’s Naples factory. Lightweight knitted hoodies and track pants had an airy quality, while flyknit high top sneakers came with soles that can be customised on purchasing.
Dondup: Fabrics were the focus at Dundop this season. Lightweight rain jackets with drawstring waists came in high shine Tyvek. The crinkly papery material that doesn’t tear was ingeniously coated to create a metallic finish reminiscent of metal. Elsewhere, a classic Harrington appeared in a laminated coated tartan and cross body bags came in the cardboard-like material normal used for denim tags.
DSquared2: This season DSquared2 designers Dean and Dan Caten took to the frontline with a military inspired collection. Recognisable elements of army uniforms were cleverly patchworked together to create bombers and multi-pocket cargo pants. Voluminous trousers were cut in army green parachute silk, while camouflage print was spliced together with graphic shots of bold colour in a series of field jackets. Souped-up sneakers of tank-like proportions were ready for action.
Canali: Designer Hyun-Wook Lee’s debut S/S 2019 collection for Canali had an easy elegance that breezed through the heat of Milan Fashion Week. Lightweight construction was key – unstructured almost shirt-like blazers and bomber jackets in wool silk linen blends were teamed with matching trousers offering new suit propositions. Fine crew neck knits offered a nonchalant alternative to the workday shirt, while a new line of smart tennis shoes grounded the laidback mood.
Receive our daily digest of inspiration, escapism and design stories from around the world direct to your inbox.
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.
-
This Canadian house is a precise domestic composition perched on the Nova Scotian coast
Bishop McDowell completed a new Canadian house overlooking the Atlantic, using minimal details and traditional forms to create a refined family home
-
‘With a small gesture of buying a postcard, we all become copyists’: the Louvre’s celebration of copying speaks to human nature
Contemporary artists are invited to copy works from the Louvre in a celebration of the copyist’s art, a collaboration with Centre Pompidou-Metz
-
Serious cyclists now have serious options, courtesy of two new models from Canyon
With two new bikes, the Endurace: ONfly e-bike and Endurance: AllRoad, Canyon is innovating with both price and performance
-
Let there be light: a closer look at Prada’s stripped-back S/S 2026 show set
‘This is the first time the Fondazione is completely bare, with the light coming in,’ said Raf Simons backstage at Prada’s ‘light, fresh, colourful’ and ‘human’ S/S 2026 men’s show in Milan
-
The standout shows of Milan Fashion Week Men’s S/S 2026: Prada to Dunhill
Wallpaper* picks the very best of Milan Fashion Week Men’s S/S 2026, from Miuccia Prada and Raf Simons’ ‘light, fresh’ and ‘human’ display to Dunhill’s exploration of English dress codes
-
Milan Fashion Week Men’s S/S 2026: live updates from the Wallpaper* team
From 20-23 June, Milan Fashion Week Men’s arrives in the Italian fashion capital. Follow along for a first look at the shows, presentations and other fashion happenings, as seen by the Wallpaper* editors
-
What the Wallpaper* editors are looking forward to at Men’s Fashion Week S/S 2026
As Men’s Fashion Week S/S 2026 begins in Florence, the Wallpaper* style team select the moments they will be looking out for – from Jonathan Anderson’s anticipated Dior debut to outings from Wales Bonner, Kiko Kostadinov and Prada
-
The best fashion moments at Milan Design Week 2025
Scarlett Conlon discovers the finest fashion moments at Salone del Mobile and Milan Design Week 2025, from Loewe’s artist-designed teapots to The Row’s first home collection
-
Milan Fashion Week A/W 2025 highlights: Prada to Giorgio Armani
Wallpaper* picks the best of Milan Fashion Week, from Miuccia Prada and Raf Simons’ portrait of ‘raw glamour’ to Giorgio Armani’s return to his roots
-
Milan Fashion Week Men’s A/W 2025 highlights: Prada to Zegna
Despite a reduced schedule, Milan Fashion Week Men’s A/W 2025 retained momentum thanks to high-wattage shows from Emporio Armani, Dolce & Gabbana, Zegna and Prada. Wallpaper* fashion features editor Jack Moss picks the best of the week
-
Milan Fashion Week S/S 2025 highlights: Dolce & Gabbana to Bottega Veneta
Wallpaper* fashion features editor Jack Moss selects the best of Milan Fashion Week S/S 2025, from Dolce & Gabbana’s homage to Madonna to childlike wonder at Bottega Veneta