Bite-sized style news to know what’s happening in menswear this September
Jaden Smith is made Louboutin's first men's creative director, Valentino collabs with Vans, Dior releases its new slouchy bag, and more
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WELCOME TO ‘Bite-sized style news’, a monthly dispatch where we discuss the news, rumours and conversations that are dominating the men’s style discourse, and therefore, our Esquire water cooler chitchat.
Scroll on for this week’s edition.
Jaden Smith is Christian Louboutin’s first men’s creative director
As the fashion world ramps up for its biggest season yet this month, with over a dozen new creative directors making their debuts, a new appointment came in this week from an unexpected house. Parisian shoemaker Christian Louboutin – known for his ‘red bottoms’, as Cardi B once rapped – has made Jaden Smith the brand’s first men’s creative director.
In his new role, the actor, musician, and overall style muse will oversee four collections a year, encompassing men’s shoes, leather goods, and accessories, as well as shaping the visual language of the brand’s campaigns and events for its dedicated male customer, who represent 24 per cent of their revenue.
Smith, 27, first met Louboutin, 62, while visiting Paris in 2019, where the two immediately hit it off with a shared admiration for each other’s vision and creativity. “When I first met Jaden, I saw in him a natural fit for the maison; his world is rich and multidimensional, his style and cultural sensibility are inspiring and his curiosity and openness are remarkable,” Louboutin shared in a statement. “I felt that with his creative direction our men’s collection would evolve in an exciting and dynamic way.”
“Merging my vision with Christian’s comes quite naturally because we see the world in a very similar way. There’s a shared respect for creative freedom, and I think that’s why it works,” said Smith. “Christian has given me a place to explore, to learn, and to create freely.”
Smith’s first collection will be revealed in January 2026, during men’s autumn/winter 2026 Paris Fashion Week.
The Valentino x Vans collab is the plimsoll comeback we’ve been waiting for
Noughties nostalgia was rife during the spring/summer 2026 show at Paris Men’s Fashion Week in June, chief among them was the plimsoll – the rubber-soled sneakers popular in skate culture. While Vans has stood by the style since its founding in 1966, the Vans Authentic recently got a new cheerleader in Valentino creative director Alessandro Michele. Though this isn’t your regular designer collab fare.
The Italian fashion house skipped the usual hallmarks of a luxe interpretation of a mass product, instead opting to stay with the California brand’s canvas uppers and vulcanised rubber soles. Featuring six designs that riff on the popular checkerboard print with acidic and fruity colourways, the shoes are first and foremost designed to skate in. First seen on the autumn/winter 2025 Paris runways in January, the collab arrives in stores this month and on Valentino.com, with a price tag of $730 a pair.
Dior introduces its slouchy hobo bag
The latest bag trends aren’t veering big or small, but slouchy. You see, structured bags to hold up your belongings in place are all well and good (professional, even), but lately, a malleable, buttery bag has been a style move that we’re noticing in the fashion world. Holding your bag by tucking it into your elbow instead of by its designed handles, for example, is kind of the current look.
The newest development in the space comes from Christian Dior in their new Slider hobo bag, which made its runway debut in January during Kim Jones’ last collection for the French house. Made of supple calfskin leather, the cavernous bag will elegantly droop in the centre when the ‘slide’ handles are held up. (Models wore the straps over the shoulder and bunched in the hand, as per above.)
The main compartment is accessed through double-zipper closures with enough space to fit work or weekend essentials. Arriving in stores and on Dior.com in black, grey and ‘cognac’, it’s designed to fit in easily with your rotation year-round.
Learn more about and buy the bag here.
Rimowa releases a new hue with flying colours
At this time of year, rarely do international brands have releases that fit into our summertime. Thankfully, Rimowa has our back on this one with their seasonal hue: Sky Blue. The German luggage-maker has released the new colour in their Cabin, Check-In L, and Trunk Plus sizes, which are ideal for your longer travels and where style is a consideration. Build-wise, Sky Blue is available in their Hybrid collection (for now), which combines a lightweight polycarbonate shell with aluminium corners and frame. With those in mind, these pieces will physically and stylistically endure for many trips to come.
Learn more about and buy the collection here.
Seiko wants you to pair your watch with your cocktail
Rare and esoteric are two ingredients for a watch’s success. In the latest development of their Presage Cocktail Time series, Seiko has released ‘The Conte’, which features a red dial as seductive as a Negroni. Exclusive to the Australasian market and limited to 1000 pieces (told you it would be rare), it’s powered by a Calibre 4R35, aka the Japanese watchmaker’s watch movement with a 41-hour power reserve and date-display. Encased in rose gold and finished with brown leather straps, it makes for an elegant timepiece for the evening. (To boot, we’d recommend wearing it to Sydney’s favourite Negroni bar, which happens to be called Bar Conte.)
Learn more about the watch here.
Stylist Elliot Garnaut reimagines an A-Esque icon
If you had the chance to collab on your favourite product, what would it be? For Aussie celebrity stylist, its A-Esque’s Original Grocer Tote, a roomy, rectangular box tote that’s taken him from photoshoots to the supermarket. Garnaut’s touch on the Melbourne-based brand’s classic style takes it up a notch in Italian leather and suede, coming in a slew of earthy neutrals like brown, burgundy and khaki. It’s the original but elevated with the same utilitarian features of tall handles for it to be held in hand or slung over the shoulder.
Related:
Jonathan Anderson joins Dior Men’s. Here’s what to expect
Jack Draper on court style, summer in London and life after winning Indian Wells
