I’m Taking a Break From Trends—8 Classic Winter Looks I’ll Be Wearing Instead

While there's no denying the importance of trends in keeping fashion fresh and inventive, it's worth picking and choosing the ones you buy into. In fact, there is something to be said for building a wardrobe which altogether eludes them. If you want your clothing to outlast seasonal tastes, consider a more future-proof approach to shopping, focusing on forever buys over fleeting fads. Personally, I believe there's room for both—in my own wardrobe, I try to keep things timeless, but if a trend particularly excites me, I'll allow myself to try it out in a low-stakes way. If I don't get the wear out of it within a few months, I'll simply flog it on Vinted, pass it on to a friend or hand it over to a charity shop.

Generally, though, I get the most joy out of piecing together a simple, classic look that I know I can re-wear for years to come. And I've found that amongst the hundreds showcasing trend-led looks on Instagram and during Fashion Month, there are plenty who adopt a similar attitude to dressing. In fact, I recently went down a street-style rabbit hole and was pleasantly surprised by how many understated outfits I came across. Fresh from the streets of Paris, Copenhagen and New York, the eight ensembles below are at the top of my list to re-create for the coming season.

1. Trench Coat + Turtleneck + Loose Jeans

Classic Street Style Outfits: a trench coat styled with a turtleneck and baggy jeans

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The Style Stalker For Who What Wear

Style Notes: It's not uncommon to spot a trench coat outfit on the streets of Paris, but this one featuring baggy light-wash jeans feels like a contemporary take on the look.

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I've heard only rave reviews about COS's cashmere jumpers.

2. Check Blazer + Bright Knit + Tailored Trousers

Classic Street Style Outfits: a check blazer styled with a bright knit and tailored trousers

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The Style Stalker For Who What Wear

Style Notes: We'd place money on this check-blazer-tailored-trousers ensemble still being relevant in ten years' time. Possibly even twenty.

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3. Biker Jacket + Slip Dress + Mary Janes

Classic Street Style Outfits: a biker jacket styled with a slip dress and mary janes

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The Style Stalker For Who What Wear

Style Notes: An easy way to toughen up a pretty silk dress and Mary Janes combo? Add a timeless biker jacket into the mix, like this Paris Fashion Week attendee.

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This has a slightly longer length than most biker jackets, which makes it more suitable for the colder months.

Prepare for compliments when you step out in these Mary Janes.

4. Suiting + Loafers

Classic Street Style Outfits: a suit styled with loafers

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The Style Stalker For Who What Wear

Style Notes: Slouchy tailoring is trending big time in 2023, but suiting like this will never date—especially when paired with timeless loafers.

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Easy to transition from day-to-night with a simple shoe change.

5. Wool Coat + White Jeans + Lace-Up Boots

Classic Street Style Outfits: a wool coat styled with white jeans and lace-up boots

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The Style Stalker For Who What Wear

Style Notes: A chic wool coat is a wise investment; come winter, you can toss it on over any outfit and immediately look put-together.

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Ecru jeans work just as well at this time of year as they do in summer.

The whipstitching really sets these boots apart.

6. LBD + Knee-High Boots

Classic Street Style Outfits: an LBD styled with knee-high boots

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The Style Stalker For Who What Wear

Style Notes: If it involves an LBD, it's an instant winner in our books. The combination of the above-the-knee hemline and tall boots is perfection.

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£28 for a dress this versatile? Sounds like a good deal to me.

Melie Bianco makes great dupes for designer clutches.

I have these and can confirm just how comfy they are.

7. Longline Coat + Maxi Dress + Ballet Flats

Classic Street Style Outfits: a longline coat styled with a maxi dress and ballet flats

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The Style Stalker For Who What Wear

Style Notes: When in doubt, look to the Danes for effortless outfit inspiration. Case-in-point: this impeccable maxi slip dress styling. The ballet flats balance out the heavy coat nicely.

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You could also style this over a turtleneck for a more casual feel.

8. Faux Fur Coat + Leather Trousers + Chunky Boots

Classic Street Style Outfits: a faux fur coat styled with leather trousers and chunky boots

Photo:

The Style Stalker For Who What Wear

Style Notes: This look simultaneously feels fresh and familiar. Leather trousers are huge this season, and they look so cool teamed with faux fur and all-weather boots.