With her French, Spanish and Polish heritage, designer Emma Raphaëlle Rotenberg is no stranger to drawing inspiration from multiple sources, so it’s no wonder that the brand she founded in 2018, Rowen Rose, exhibits an eclectic mix of cultural references. The fall/winter 2019 collection blends her signature ’20s prints and ’80s silhouettes with moments from the film Double Dealing, which involved casinos and opulent art deco backdrops.

Italian brand Loro Piana, renowned for its luxurious cashmere designs, stresses the importance of dressing from the feet up this fall with a fresh collection of knitted 360 Lp Flexy Walk sneakers for men and women. Made from lightweight and breathable Wish wool in a wide range of colours, from cobalt to rust, they are meant to be your walking buddies from Monday to Sunday.

The shorter days of fall may have you reaching for darker hues, so you’ll have to rely on subtle textures and patterns to make a statement. Pleats are an easy way to start (plus they add a pretty flutter to your every step), while polka dots go a long way when jazzing up a monochromatic ensemble. To finish, drape a cosy knit nonchalantly over the shoulders for an added layer—without obscuring the outfit.

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Designers are putting the cool back into school this season, with the likes of Hermès and Tom Ford paying homage to private school uniforms. Think plaid patterned blazers, chunky cardigans and, for accessories, leather backpacks, preppy silk ties and signet rings, like those traditionally worn by Yale graduates. The latter is reimagined at Fendi this fall with intertwining Fs designed by Karl Lagerfeld. See, it’s never too late to get a fashion education.

What did Monty Clift, Marlon Brando and James Dean have in common? Besides impeccable hair, they embodied a timeless charm, a trait that inspired Brunello Cucinelli’s fall/winter 2019 accessories. The new backpack, featuring three big pockets on the sides and fastening belts in cocoa-hued leather on camel corduroy, is the modern gentleman’s best friend, whether in a conference room or on a cabin getaway.

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Hong Kong-born designer Ka Wa Key is known for exploring concepts of gender fluidity and soft masculinity through his menswear, and the results have landed him dozens of accolades, including nominations for the 2016 H&M Design Award and the 2018-19 Woolmark Prize. For fall/ winter 2019, the Royal College of Art graduate reinterprets American denim and cowboy-inspired garb with cowhide coats, corduroy overalls and baggy, utilitarian trousers.

Many of the digital prints featured on puffers and knits were hand-painted by Key, while the skin-tight tops and plunging shearling coats reflect his sensual aesthetic. Key has garnered an international following, having showcased his collections during fashion weeks in London, Paris, New York, Shanghai and Tokyo, and now occupies coveted shelf space at multi-brand fashion outlets like Opening Ceremony.

Not ready yet to dip into your all black hibernation wardrobe? Take styling cues from fall foliage with an of-the-moment bronze suit to take you through this seasonal transition. Keep the accessories playful with a wide brim hat, sandals and a tie thrown nonchalantly over the shoulder. Remember, it’s all in the attitude.

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