6 Classic Autumn Outfits I Reach for Every Year Without Fail

I love autumn. As summer comes to a close, the mere mention of browning leaves and creamy hot cocoa is enough to send me rummaging through my wardrobe to rediscover all my cosy cold-weather clothes. Goodbye, cotton dresses and strappy sandals. While I’m always careful not to unnecessarily add to my ridiculous mountain of knitwear, I can’t help but take a peek at which fresh trends are emerging this time of year and how my favourite designers are interpreting them.

No doubt about it: This year’s trends are good. So good I’ve composed a fantasy wish list that would likely cost the value of a small house to fulfil. But as someone who describes their style as classic when asked, I’m forever on the hunt for investment pieces that I know I’ll get endless wear out of, and this remains my priority for autumn/winter 2024. Thank goodness for willpower.

When I shop, I shop with outfits in mind. And there are certain ensembles that I look forward to re-creating each time autumn rolls around. Cool, classic and comfortable—I'm pretty sure these outfit formulas are universally loved. But in case you're yet to discover them, scroll on for the six timeless looks I'll be wearing all season long.

6 Classic Autumn Outfits That Have Always Looked Good:

1. Blazer + Jeans

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(Image credit: @symphonyofsilk)

Style Notes: This trend-defying pairing is a French-girl favourite, which obviously means it's a Who What Wear favourite, too. Style yours with a plain white tee and two-tone pumps just like Lorna did, or switch the dainty shoes out for a pair of trainers.

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2. Satin Midi + Ballet Flats

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(Image credit: @thandimaq)

Style Notes: I want to buy every dress Thandi Maq wears, and this long-sleeved satin number is no exception. I love the addition of white ballet flats to give this classic look an unexpected update; something I'll definitely be trying this season.

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3. Trench Coat + Tailored Trousers

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(Image credit: @brittanybathgate)

Style Notes: All hail the queen of timeless dressing, Brittany Bathgate. The combination of an oversized trench coat and loosely tailored trousers is so chic, yet so comfortable. In other words, just the kind of outfit I aim for day to day.

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4. Knee-High Boots + Mini

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(Image credit: @aida.bdji)

Style Notes: Knee-high boots were made to be worn with short hemlines. Whether you opt for a miniskirt or dress—or even a pair of leather shorts—you'll look straight out of the swinging ’60s. Take note from Aïda, and throw a boxy jacket over top to modernise the look.

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5. Chunky Knit + Long Skirt

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(Image credit: @emmarosestyle)

Style Notes: Whether you're WFH or on the go, this outfit meets all the essential criteria—it's comfy, effortless and composed of items that can be worn a hundred different ways. Wear your hair in a low bun like Emma Rose did to let that turtleneck shine.

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6. Leather Bomber + Pointed Boots

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(Image credit: @ingridedvinsen)

Style Notes: Ingrid has nailed the sleek laid-back dress code with this look. Trust us—a leather bomber and pointed boots are two pieces you'll never regret investing in.

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Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.