Top Fall/Winter 2025 fashion trends and best buys according to 4 experts

True style is all about the subtle signatures – a casual rolled sleeve, a distinctive piece of jewellery, or a pair of bold frames. It’s these quiet but deliberate choices that define a look.

Savina Chow

According to Savina Chow, who has been a fashion content creator since 2017, style isn’t limited to what you wear. It seeps into every aspect of life, from the music you play to the art you surround yourself with. “I’m a big believer that personal style changes with life’s seasons, and can be learnt through trial and error.”

Best of Season: Soft and Slouchy Bags

Prada Tumulte Small Nappa Leather Bag, $4,800, Prada

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Savina’s fall shopping list

Suede lace-up sneakers, $620, Acne Studios

Credit: Acne Studios

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“Are these sneakers, loafers, slippers or ballet flats? Can’t pick one, so why not have a pair that checks all those boxes? They are so cute when paired with white socks!”

Spy large leather bag, $6,590, Fendi

Credit: Fendi

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“The Fendi Spy Bag – one of my favourite styles from 2005 – stands out with its twisted strap detail and oversized, soft leather silhouette that exudes relaxed luxury.”

Corduroy blazer, $5,070, Yves Saint Laurent

Credit: Yves Saint Laurent

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“Corduroy is having a moment, and the brown blazer is leading the charge. I would style it with a classic white tee and wide-leg denims.”

Bessie Ye

For fashion designer Bessie Ye, true style comes with ease. “You can always tell when someone isn’t trying too hard,” she says. “There’s a quiet confidence in that – it’s the difference between wearing the clothes and letting the clothes wear you.”

Bessie believes style is something that can be cultivated over time. Her personal style icons reflect that same balance of effortlessness and thoughtfulness: Lucy Chadwick for her understated elegance, and Miuccia Prada and Sarah-Linh Tran for their ability to stay classic while pushing fashion forward.

Best of Season: Lingerie Dressing

Chloe Fall/Winter 2025, Look 20

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Bessie’s fall shopping list

Antique leather pointed pumps (85mm), $2,090, Prada at Farfetch.com

Credit: Prada

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“I love the idea of pumps that look distressed – worn and lived-in, breaking the stiffness of a classic pointed toe.”

Classic calfhair belt, $1,009, The Row at Net-a-porter.com

Credit: The Row

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“The tactility is irresistible – it adds a playful touch to the outfit.”

Lace-trimmed dress, $830, Carven at Farfetch.com

Credit: Carven

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“I’ve always loved a nonchalant vibe – like wearing underwear as outerwear – and a lingerie slip dress adds just the right touch of sensual texture.”

Aviator-style acetate and silver-tone sunglasses, $1,067, Bottega Veneta Eyewear at Net-a-porter.com

Credit: Bottega Veneta Eyewear

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“This season’s eyewear trend blends ’70s sophistication with boho elegance to elevate every look.”

Daryll Alexius Yeo

Daryll Alexius Yeo believes the most stylish people share one key trait: a touch of irreverence. They don’t just follow fashion rules – they bend them to fit their own vision. With over a decade of styling experience, he sees personal style as something cultivated, not innate. “That’s what makes it exciting – it’s a journey of self-discovery through fashion,” he says. 

His advice? Stop dressing for validation. When you let go of seeking approval and trust your own taste, clothes become more than outfits – they become an extension of yourself. When it comes to style icons, Daryll points to the Olsen twins. Their precise, understated and timeless aesthetic proves that true style comes from being authentic.

Best of Season: Oversized Belts

Schiaparelli Fall/Winter 2025, Look 3

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Daryll’s fall shopping list

Pleated wool blend plaid skirt, $2,250, Loewe

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“Plaid is having a major moment, seen from miniskirts at Miu Miu to elegant styles at Missoni. A plaid skirt can be preppy or rebellious, depending on how you style it. For a fresh look, pair a tiny plaid skirt with oversized knits and biker boots, or a slouchy tank and sneakers – the key is to embrace the clash for a modern vibe.”

Oversized leather jacket, $10,200, Khaite

Credit: Khaite

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“Luxe outerwear like Saint Laurent’s and Hermes’ funnel-neck pieces bring rebellious, ’80s-’90s nostalgia with moody glamour. The oversized leather jacket is a key investment. Add edge over a silk slip or keep it cool with baggy jeans and loafers for a laid- back style.”

Slouchy leather boots, $2,229, Isabel Marant at Net-a-porter.com

Credit: Isabel Marant

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“Slouchy boots return this season with loose, liquid-leather shapes that soften sharp tailoring, or add edge to feminine looks. Think louche glamour a la Saint Laurent and Balmain, with exaggerated shafts and bold attitude. These boots don’t march – they swagger with purpose.”

Lena Kamarudin

After two decades in fashion, Lena Kamarudin knows what truly defines style. “The most stylish people aren’t slaves to trends – they have a fierce sense of their own aesthetic, and know exactly what suits them. They mix and match pieces in a way that flatters their body and feels authentic.”

She believes that trying something new should never feel forced. If you put something on and it feels unnatural – or just not you –ditch it. When in doubt, keep it simple and chic. Her go-to? A classic T-shirt or sweatshirt paired with flared jeans. She’s all about the accessories – think layered necklaces, stacks of bracelets or bold, chunky bangles and a pair of simple hoops. Lena draws inspiration from the daring culture and fashion figure Michele Lamy, and ’60s style icon Talitha Getty – both legends for their fearless takes on fashion.

Best of Season: The Exaggerated Hip

Alaia Fall/Winter 2025, Look 9

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Lena’s fall shopping list

Levi’s x Junya Watanabe cotton denim acrylic faux fur jeans, $1,550.46, Junya Watanabe at Club21.com

Credit: Junya Watanabe

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“I love a good statement piece to mix-and-match with the basics. I will never get bored of these fur-trimmed jeans because there will never be a dull day in these, whether you style it with a simple grey T-shirt, chic turtleneck top or an embellished cropped top.”

Thong fishnet sandals, $920, Alaia

Credit: Alaia

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“Is it a shoe or a sandal? Either way, it’s unmistakably Alaia in its signature mesh. I’d wear it with an oversized blazer and tailored trousers or with a cute summer dress for the beach. Now that’s versatility.”

Belted suede tote, $1,821, Toteme at Net-a-porter

Credit: Toteme

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“Brown is everywhere this season, but when it comes to bags, it’s brown suede that’s stealing the spotlight. Luxury labels like Saint Laurent, Prada, Khaite, and Coach are all embracing the soft, textured finish in their latest collections. Smaller, independent brands are also delivering standout suede styles. Case in point: this gorgeous piece from Toteme.”

Fish earrings, $1,320, Bottega Veneta

Credit: Bottega Veneta

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“Who doesn’t love a kitschy accessory, or three?”