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Winter Menswear Trends to Know This Season

From soft tailoring and versatile outerwear to refined accessories, this season’s menswear trends prioritise comfort, functionality, and understated elegance.

Menswear is entering a quieter, more considered phase. The emphasis is on ease, quality, and versatility: clothing that feels current but is built for longevity.

For winter, the most compelling looks are those that balance refinement with practicality. The utility jacket, for instance, has become a modern essential. Clean-lined and functional, it brings together technical fabrics, tailored proportions, and a sense of urban readiness. It’s the kind of piece that moves easily between city days, weekend escapes, and unpredictable weather, while still feeling elevated.

Layering remains central to the season, with knitwear, gilets, and overshirts forming the foundation of a well-composed wardrobe. There’s a renewed appreciation for pieces that nod to heritage dressing, from chunky textured pullovers and patterned vests to plush cardigans with a slight scholarly appeal. Knitwear takes on many moods: classic patterns for a heritage sensibility, structured cardigans for creative layering, cashmere polo necks for quiet elegance, and crewnecks for effortless everyday styling. The result is a modern interpretation of vintage refinement – polished yet relaxed.

Tailoring follows the same instinct. Suits and separates are becoming softer, more fluid, and easier to wear, while still holding their shape. Wool brings warmth and sophistication, while corduroy introduces texture and a casual richness. Deep chocolate browns, navy, red, hunter green, and orange stand out as key colours, offering depth and an understated alternative to more predictable neutrals.

As the season becomes less defined and weather patterns more unpredictable, adaptability is increasingly important. Wardrobes that function best are built around pieces that work across travel, work, play, and the unexpected moments in between. Versatility is no longer simply practical. It’s become a mark of good taste.

Footwear is also shifting towards a smarter everyday language. Loafers and boots are stepping forward as natural companions to both denim and relaxed tailoring. A well-made loafer brings polish without feeling formal, while a refined ankle boot adds structure and confidence to cool-weather dressing.

Accessories complete the picture with a sense of restraint. In watches, oversized silhouettes are giving way to smaller, more delicate timepieces that feel personal, understated, and quietly chic. Sunglasses, meanwhile, offer room for personality. Coloured lenses add visual interest and a subtle change of perspective, adding the final note to a wardrobe built on intention, ease, and enduring style.

  • 1 . Milano Madison sweatshirt jacket in a stretch cotton blend, POA, available from July at the Boggi Milano store in Sandton City
  • 2 . Initiales College Monogram heritage reversable belt in brown, POA, Louis Vuitton
  • 3 . Wool tailored trousers, R20 000, Zegna
  • 4 . Burgundy crew V-neck cashmere jumper, R15 100, Turnbull & Asser
  • 5 . Medium GG duffle bag with Web, R 54 000, Gucci
  • 6 . Doucals luxury handmade Italian suede loafers, R9 450, available exclusively in South Africa at GERI
  • 7 . Club chain bracelet, POA, Louis Vuitton
  • 8 . Light navy corduroy Charles trousers, R12 600, Turnbull & Asser
  • 9 . Bill large sunglasses, R2 995, Ray-Ban
  • 10 . Dark chocolate Greenwich knitted overshirt, R27 300, Turnbull & Asser
  • 11 . Black watch tartan telescopic umbrella with whangee crook handle, R11 000, Turnbull & Asser
  • 12 . Dark brown cashmere shawl collar cardigan, R43 300, Turnbull & Asser

Images: Supplied

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JUly 2026

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