Forever Trending: The History Behind 6 Classic Winter Fashion Items Editors Always Come Back to

The autumn/winter runway collections will always introduce new styling tricks and viral trends—for 2025, Prada introduced the loafer boot, Chloé ushered in a new take on aristocratic styling and chocolate brown was undoubtedly the colour of the season. However, regardless of all this newness, there are certain trends that we return to every autumn/winter and that will always be big business for brands from September onwards.

The autumn collections are defined by a back-to-school mentality—traditionally, this is the time of year when everyone invests in the hard-working building blocks of a wardrobe, from ankle boots to a wool coat. While summer might invite more frivolous styling opportunities, autumn is regarded as the moment to revisit the fundamentals. A winter coat or a pair of boots tends to be one of the biggest shopping investments of the year, and so naturally, this means things tend to slant more towards the classic, with items that promise longevity, instead of ingenuity.

Loafers, trench coats and blazers will feature in every autumn/winter trend report, however, subtle tweaks to fabrication and design can help to reinvent these classics each year and add another chapter to their storied history. For example, for autumn/winter 20,25 The Row shrunk the proportions of a classic trench coat, prompting a wave of mini trenches to arrive in new-in sections. Prada introduced the peep-toe loafer as a new category for the classic shoe, meanwhile, Miu Miu tweaked how we wear our cardigans, with knits pulled off the shoulder to reveal satin bras.

Even the most classic, timeless pieces can be given an image overhaul and so these classic autumn/winter fashion items continue to feel not only relevant, but fresh. Below I bring you the history and trajectory of six enduring pieces that will always feature in our autumn/winter wardrobes. Chances are you know what they are already...

6 Autumn/Winter Fashion Pieces That Will Never Date:

1. Loafers

Style Notes: As an Ivy League staple, loafers have a history with academia—wearing-in a new pair of penny loafers is practically part of any enrollment process. While origins can be traced back to Norwegian fisherman—GH Bass’s iconic “Weejuns” style which was introduced in the 1930s, is a spin on Norwegians—they are also a symbol of All-American style.

Gucci loafers, for example, were created in 1953 after Aldo Gucci, the son of the founder Guccio Gucci, was inspired by the loafers that he saw people wearing in New York, and added a horsebit loafer. While the 1953 loafers continue to be a well-worn classic, over the past 70 years the house (and its creative directors) have managed to reinvent the loafer again and again—from Alessandro Michele’s backless furry iterations to Sabato de Sarno’s stacked platforms. This is just one brand and one example of how loafers have remained an enduring staple in our autumn wardrobes.

For autumn/winter 2025, loafers once again had a central role on the runway—Sarah Burton used monochrome and white loafers to ground the suiting in her first collection at Givenchy, Miu Miu had sleek no-frills leather takes and Prada zoned in on hybrid designs, with peep-toe penny loafers and boot versions of this classic flat. Other design details that are popular for autumn/winter 2025 include deep chocolate tones, suede finishes and simple slip-on leather styles that have a lack of any ornamentation.

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2. Wool Coat

Style Notes: Wool coats and cloaks have been used throughout history for warmth, however there’s no doubt that Max Mara is the brand that has ensured this remains firmly in the fashion spotlight. The Italian brand translated tailored, traditionally masculine, camel coats into womenswear in the 80s, with a style known as the 101801 that was crafted from wool and cashmere. They have remained integral to every autumn collection, and are considered a landmark purchase that is guaranteed to look just as stylish decades later. While belted camel wool coats that are part of Max Mara’s core design DNA spike every autumn—LikeToKnowIt notes a 450% increase in searches for camel coats over the last 30 days, a trend that repeats each autumn—tailored overcoats are a classic that can be updated.

Toteme has made wool and cashmere coats central to its design vision, with its oversized coat beloved by Jennifer Lawrence known as the ‘Signature’ and cropped styles with fringing and an in-built scarf. In general, oversized, sweeping proportions elevate any design, while we love how at Chloé for autumn/winter 2025 tailored coats were paired with faux-fur stoles. While there is no shortage of references to pull for this look, Who What Wear UK’s Hannah Almassi has long cited the chocolate brown overcoat Kevin McAlister’s mum wears in Home Alone as the perfect winter coat. We have to agree. Thirty-five years later, it looks just as stylish.

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3. Cardigan

Style Notes: Knitwear is an essential staple in any autumn wardrobe, and while there are many iterations we could have selected for this list, the cardigan is a classic that keeps being reinvented. Miu Miu, a brand that has revisited the humble cardi several times, has ensured it is a key look for autumn/winter 2025 thanks to its latest approach to styling, with buttoned-up knits pulled off the shoulder to show a glimpse of the bras. While Gucci amped up the cardigan hype with its oversized chunky knit in a zesty lime green, covered in intricate embellishment, worn open over lingerie, showing this isn’t just an emblem of buttoned-up, conservative styling.

The cardigan was first worn in the military, as officer James Thomas Brudenell (the 7th Earl of Cardigan), favoured wearing knitted jackets in the Crimean War (hence the name). It originally was sleeveless, but had the buttons down the front you would recognise on a modern-day cardigan. Coco Chanel also played an important role in the cardigan story, as they were one of her own style signatures in the 1920s, along with Breton tops and strings of pearls.

Beloved by Queen Elizabeth II, cardigans have at times been more associated with WI than high fashion, however in 2019, this changed when Katie Holmes made a cardigan and knitted bra set by Khaite go viral. Six years on, the Scarlet cardigan remains a classic in the knitwear space that has spawned hundreds of replicas. Whether you opt for a neat Bree van de Kamp-coded twinset or a nostalgic homespun knit à la Shrimps, a cardigan is a forever autumn hero.

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4. Chelsea Boots

Style Notes: Boot trends come and go, however Chelsea ankle boots are as classic as it gets. We are firm believers that everyone should own at least one pair, whether they opt for a chunky sole or a classic close-fitted silhouette. They have been an integral part of London style since the Victorian era, when according to shoe lore the Queen’s shoemaker Joseph Sparkes invented the style as a practical walking and riding shoe. It wasn’t until the 1960s, however, when they were adopted by the style set that frequented the King’s Road, that this boot really became a cultural icon.

Features of a classic Chelsea include a fabric tab at the heel for easy removal, a low heel, an elastic panel at the ankle and a body that finishes just above the ankle. While the most classic iterations have a streamlined silhouette and supple leather, brands like Bottega Veneta, Ganni and Dr Martens have toughened up this boot with track soles and even biker hardware.

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5. Trench Coat

Style Notes: The trench coat is often associated with April showers, however, it is also a fundamental autumn staple that reappears every year—LikeToKnowIt, the influencer fashion app, notes that over the last 30 days, trench coats have seen a 3,188% rise in searches, a spike that is in line with an increase in searches last September.

This story is often thought to start in the trenches of WW1 (hence the name), with Burberry and Acquascutum both claiming responsibility for its origins – although their predecessors, waterproof coats known as “macks”, were created in the 1820s by Charles Macintosh and Thomas Hancock. These first, military trench coats had a double-breasted silhouette with a belt and were realised in khaki, however, a run through Burberry’s archive alone shows that the trench coat is an item that can continually be reinvented and retain cultural relevance.

An emblem of Hollywood, just this week Miranda Priestly showed up at the Dolce & Gabbana show in Milan in a glossy, vinyl belted trench from the spring/summer 2025 collection. At London Fashion Week this September Alexa Chung showed that a Burberry classic trench looks just as stylish now, as it did when Audrey Hepburn wore hers in a downpour in Breakfast at Tiffany’s in 1961.

Although the classic, oversized silhouette will always be hailed as a symbol of enduring style, making it a worthy investment, 2025 has also welcomed a number of updates to the original. The Row’s cropped trench, belted like a dress and worn with black opaque tights, has guaranteed that mini trenches have featured in many-a street style gallery this autumn, while single-breasted styles and dark, moody colours, like moss green and cocoa, are also current twists on the classic.

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6. Blazer

Style Notes: Tailoring is always a dominant feature in autumn/winter collections, as the sunlounger season comes to an end and work typically ramps up as we head into Q4. The back-to-school feeling continues far beyond graduation, and blazers aren’t just the uniform of private schools and preppy colleges, but an integral part of any autumnal wardrobe. When Harry Met Sally wasn’t just about chunky cable knits, as Meg Ryan’s chocolate corduroy blazers and heritage herringbone tailoring was an essential part of her New York in the fall aesthetic.

It was originally associated with rowing and the royal navy, but in womenswear blazers became a symbol of power, with suffragettes wearing tailored wool jackets as part of their uniform. In 1966 Yves Saint Laurent adopted the tuxedo for women, called ‘Le Smoking.’ The designer said, “a woman wearing a suit is anything but masculine. A strict, clean cut accentuates her femininity, her seductiveness, her ambiguity.” He cited Marlene Dietrich, the actress who used to wear men’s tailoring, as one of his muses for this style of dressing. Coco Chanel also played a significant part in this movement, of course, as borrowing clothes from her then-partner the Duke of Westminster while in Scotland, inspired her in the mid-1920s to create her own tweed tailoring, which had previously been reserved for menswear.

Every autumn Saville Row-style tailoring makes an appearance, and for autumn/winter 2025 the mood feels distinctly British thanks to a trend we have dubbed ‘frazzled, but fabulous.’ Valentino’s tweed oversized blazers look like family relics you’ve borrowed from your grandparents or stumbled upon on a successful charity shop visit. While a black double-breasted blazer will always be functional and stylish, for winter we also suggest you embrace Sloane styling tropes, with wool, tweeds and colours you’d expect to see in Balmoral. Before we head into the time of year when you can’t leave the house without many layers of insulation, an oversized blazer is a classic layering tool you can wear over pretty much anything.

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