Whenever I experience trend paralysis—a sense of overwhelm and indecision following a flurry of fresh trends—I overcorrect by focusing purely on classic looks. Basically, I ignore what's ‘in’ and take it back to basics, building outfits around the wardrobe heroes I know and love.
By assembling the outfit foundations with timeless pieces rather than involving trends, you can create a versatile base that allows you to incorporate current touches if desired. In 2025, this can mean adding an oxblood bag or swapping loafers for ballet flats. But at its heart, your outfit will be made up of mainstay items that won't go out of style. Think blue jeans, crew-neck knitwear and black leather boots.
I've come equipped with visual aids in the form of eight polished looks styled by some of Instagram's expert dressers. Take a look at the classic outfits below, then shop the pieces you need to re-create them (if you don't already own them, that is).
8 CLASSIC OUTFITS TO COPY THIS WINTER AND THROUGHOUT 2026:
1. Trench Coat + White Tee + Blue Jeans
Style Notes: The trench coat might be enjoying its moment in the trend spotlight, but this is one of those pieces that will never date. History has proven this sophisticated cover-up has enduring appeal—for ease, toss it on over a simple jeans-and-t-shirt formula.
Shop the Look:
When it comes to trench coats, it doesn't get better than Burberry.
A staple for every wardrobe.
I love this classic blue wash.
Burgundy is another classic that also happens to be on-trend this season.
2. Crew-Neck + Column Skirt + Knee-High Boots
Style Notes: It's slouchy sweater season, and we couldn't be happier. Tuck your knit into a straight column-style skirt to create more definition, and add black knee-high boots to elevate the look.
Shop the Look:
This is a sell-out every autumn/winter.
Such a classy piece.
A boot you'll be proud to show off.
Simply stunning.
3. Long Coat + Striped Shirt + Wide-Leg Trousers
Style Notes: A coat will make up the bulk of your outfit for the next few months, so you may as well invest in a good one. Keep the styling underneath light, comfortable and timeless and you'll be outfit repeating before you know it.
Shop the Look:
From the sharp shoulders to the mid-calf length, I love everything about this coat.
So chic.
An instant outfit elevator.
This cut is so classic.
4. Blazer + Slip Dress + Mules
Style Notes: For autumn/winter events, resist splurging on a brand new dress that might feel dated this time next year—instead, stick to a Taffy's fail-safe combo, a boxy blazer contrasted with a pretty slip dress.
Shop the Look:
This stone shade will be a perfect addition to your winter colour palette.
This is simply stunning.
Wear these all-year-round.
So sleek.
5. Cropped Jacket + Straight-Leg Jeans + Boots
Style Notes: A cropped jacket with wool in the composition is just the ticket to keeping you warm on milder winter days. Opt for high-waisted jeans and sleek boots to complete this timeless look.
Shop the Look:
This warm beige jacket is so refined.
Editors swear by these.
I'll be taking a break from black boots with this chic beige suede pair.
6. Turtleneck Jumper + Tailored Trousers + Loafers
Style Notes: I don't believe wearing a loose, chunky-knit jumper necessitates choosing a fitted trouser; lean into the cosy look like Brittany with relaxed silhouettes from top-to-toe.
Shop the Look:
Meet your new favourite jumper.
So good I included them twice.
The traditional penny loafer gets a modern refresh.
The perfect size for daily use.
7. Wool Coat + Mini Dress + Knee-High Boots
Style Notes: When in doubt, a maxi wool coat and mini dress combo will never fail to look chic. Opt for a knitted iteration and add tights and sleek boots to keep you warm.
Shop the Look:
This belongs in every wardrobe.
Wear with boots, trainers or kitten heels.
A killer pair of boots.
My dream bag.
8. Trouser Suit + Knit Top + Loafers
Style Notes: No doubt you already own a suit of come kind, so for autumn/winter, just make like Marilyn and wear over a knit top with socks and loafers. Keep on adding the layers for super cold days a polo top underneath and a maxi coat on top should do it.
Shop the Look:
Big fan of the fitted double breasted design.
These would also work so well with a cashmere knit for the office.
A classic.
This piece was originally published at an earlier date and has since been updated.
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