We all know the feeling of scrolling through old photos, only to wince at a questionable outfit choice—what was past you thinking? Maybe it was a TikTok microtrend that took over, or a bout of discount delusion during sale season. Always remember, there’s usually a reason that neon orange scarf never sold out.
The good news? There’s one easy way to avoid that feeling altogether: focus on outfits that look just as chic today as they will in ten years’ time. So, with that in mind, I’ve rounded up five timeless winter outfit formulas to recreate right now. The overarching theme—whether you’re drawn to a leather skirt look or an oversized grey coat—is simple: embrace the “less is more” approach. Think pared-back accessories, minimalist colour palettes and outfits built around a few well-chosen pieces. The simpler the outfit, the fewer elements there are to date.
But that’s not to say timeless has to mean boring. Instead, it’s about quietly confident styling—playing with proportions, adding classic pops of colour, and investing in well-fitting pieces that truly stand the test of time. Scroll on for the forever-outfits stylish women in Paris, London and Stockholm are wearing now and that are well worth adding to your winter moodboard.
5 Timeless Winter Outfit Formulas to Re-Create:
1. Grey Coat + Jeans + Ballet Flats
Style Notes: Anouk Yve is a master of timeless dressing, but this grey coat, jeans, and ballet flat look might be my favourite yet. It’s effortlessly chic, incredibly easy to recreate, and the perfect reminder that less really can be more—especially when you’ve got a great coat.
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A grey wool coat offers the same polish as black, just softer—and far less lint-prone.
A great pair of jeans should last in your wardrobe until you grow out of them, and that's sure to be the case with this Agolde pair.
I challenge you to name a more timeless shoe than a black ballet flat.
I own this exact bag in grey and even a laptop, water bottle and trainers can fit inside.
2. Jumper + Leather Skirt
Style Notes: Leather skirts are undeniably chic—the kind of wardrobe staple that earns its place season after season. So naturally, one of our timeless winter outfit formulas had to include the elevated essential. Here, Abi Marvel proves why brown and yellow remain a classic pairing, while making yet another compelling case for the Manolo Blahniks found in every luxury fashion fan’s wardrobe. Proof that investment items are often worth their price tag.
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Buttermilk yellow may have been the trending shade of last season, but it's also a colour that never dates.
Look after your leather and it will last a lifetime in any wardrobe. Few fabrics are more timeless than that.
With Anna Wintour and Carrie Bradshaw as longterm fans, Manolo Blahnik's are one of the most timeless shoe brands to invest in.
These silver hoops will easily become your everyday go-to.
3. Trench Coat + Jumper + White Jeans
Style Notes: Jeans and a trench coat are the unspoken autumn uniform of many a fashion fan, but Hannah Lewis is here to prove the look can feel a little more polished with a few tiny tweaks. Swap your blue denim for white for a more neutral fit, your floaty trench for a minimalist car coat, and those trusty trainers for loafers. Oh, and don't forget your V-neck jumper, did you know they're trending again? Now it's truly timeless.
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If you love the look of a trench coat but are fed up with the belt falling off (me too), try this beige car coat instead.
I bought these jeans a few months ago and have rarely taken them off since.
V-neck jumpers have had a bit of a rebrand this year, so expect to start seeing the retro cut everywhere.
Few shoes are as timeless as a loafer, and Alohas made to order business model makes them a more planet-friendly pick.
4. Boots + Jeans + Blazer
Style Notes: There's something incredibly Lady Di about this look—proof that it's totally timeless. Simply tuck your light-wash jeans (all the more attention-grabbing) inside knee-high boots and layer up with a roll-neck and blazer. Bonus points if you add the red cap like Marilyn, adding a particularly preppy spin.
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Every wardrobe needs a classic black blazer, and this Isabel Marant style is a favourite amongst my fashion editor friends.
This wool-cashmere blend jumper is sure to be super cosy.
A light-wash denim will draw extra attention to your outfit.
Knee-high boots are an easy go-to throughout the colder months, so opt for a pair that's versatile enough to wear many ways.
5. Silk Skirt + Boots + Leather Jacket
Style Notes: Jeans and coats may be the most typical timeless winter outfit that springs to mind (and for good reason), but Hannah Lewis makes a strong case for the lace-trimmed skirt. Perfect for evenings or days when you want to feel just a little bit elevated.
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A boxy leather jacket adds an instant cool factor to any outfit.
You'll have spied satin skirts with a lace trim on a number of your chicest friends by now, and thin knits, T-shirts and cotton shirts all pair perfectly.
I'm the proud owned of three pairs of Staud boots and they're all incredibly comfortable.
Yes, the sun still shines in winter (if only for a few hours), so you can still have a chic pair of shades to hand.
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