INSPIRATION AND ADVICE
7 CASUAL WINTER OUTFITS FOR EVERY PLAN
By Emma Strawbridge, 29 September 2025
Picture: Getty
#1: A FESTIVE MARKET OUTFIT
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Pictures: ASOS
Whether you’ll be heading to Hyde Park’s Winter Wonderland, a European market or something more local, a festive market is a must in winter. But what does a Christmas market outfit look like? You’re probably going in the evening, which means it’s going to be cold (colder than it would be in daytime, anyway), and that means you need a big jacket. Faux fur is everywhere this season, so it seems like the only logical choice. Style it with a knitted winter dress or your favourite jeans – as statement as they look, faux-fur coats are actually easy to style. Just don't forget to wear your winter boots... Christmas markets can get surprisingly muddy.
GET THE LOOK:
ASOS DESIGN collarless longline faux fur coat in snow leopard, £85
Levi's cinch baggy jeans in indigo, £70
#2: AN ICE SKATING OUTFIT
If you’re planning a cute evening ice skating this winter, remember that as well as being able to balance on the ice, you need an outfit that balances practicality with style. Layer up warm with thick knits and coats (which also provide extra padding in case of falls!), and use these layers as a chance to get festive. Choose a Fair Isle or argyle knit in a statement colour to up the dopamine levels, and wrap up in style with a knitted headscarf and mittens.
GET THE LOOK:
ASOS DESIGN argyle brushed boyfriend cardigan in red, £50
Abrand Jeans 99 low mega baggy jeans in indigo blue, £109
#3: A WINTER WALK OUTFIT
Picture: Getty
Pictures: ASOS
Take your casual winter looks up a notch and do it like the Scandi girls this season. Layer some off-duty track pants (you can’t go wrong with adidas) with a baggy jumper, and make extra layers look intentional by tying them around your shoulders. You might want to throw on a big coat too – a classic longline felt coat would look great with this look. The last touch? Winter accessories. A slouchy leather bag is weather-proof and stylish, while a fluffy hat and leather gloves bring all the texture you could need.
GET THE LOOK:
ASOS DESIGN oversized jumper in blue and chocolate stripe, £32
adidas Originals Firebird track pants in navy with badge, £65
#4: A BONFIRE NIGHT OUTFIT
Pictures: ASOS
Lean into gorpcore for your bonfire night outfit. Warmth, comfort and waterproofing are essential for an evening spent in a muddy field, but that doesn’t mean you can’t look good. That’s where gorpcore essentials come in: a padded jacket from a trusted brand like The North Face, some sturdy trainers that’ll tackle slippery ground with ease and a crossbody bag, which means you can go hands-free when you get that inevitable burger and mulled wine from the food trucks. Just add a jumper or fleece and some cold-weather accessories (hats, scarves, gloves etc.) and you’re set.
GET THE LOOK:
The North Face Hyalite down jacket in black, £215
ASOS DESIGN oversized cargo trouser with pleats in khaki, £40
#5: A WINTER DINNER OUTFIT
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Pictures: ASOS
When you plan a midweek dinner after work with friends, the what-to-wear dilemma stems from needing to be office-appropriate and wanting to look cute. You can definitely take an outfit change to work, or you could try an outfit like this. Plus, you’d be ticking off multiple autumn trends in one: layering a slip dress over tailoring, chocolate brown tones and silver details. The tailored trousers keep things SFW, while the longline top or slip dress and metallic accessories make it fun for party-season plans – but it somehow still feels casual? That’s down to the loose proportions, flat shoes and slouchy straight-from-work bag.
GET THE LOOK:
ASOS DESIGN satin lace trim asym cami top in chocolate, £32
Vero Moda dad fit tailored trouser co-ord in chocolate, £30
#6: AN OUTFIT FOR A COSY NIGHT IN
Pictures: ASOS
Hibernation season is upon us, and sometimes you just need a night in with a movie marathon and your full self-care routine. After your everything shower, get cosy in a pair of cute pyjamas (the cute part is essential), light a candle and hunker down into some serious skincare, which is where the makeup headband comes in. Extra comfort comes in the form of a fluffy dressing gown and slippers, and then you’re ready for an evening of movies and your favourite snacks.
GET THE LOOK:
ASOS DESIGN pyjama top co ord in burgundy stripe, £24
Loungeable cosy borg mule slipper in cream, £14
Kitsch Fabric Puffy Headband 1 Pack - Black, £10
Loungeable cosy sherpa hooded maxi dressing gown in mink, £30
#7: A WINTER DATE-NIGHT OUTFIT
Picture: Getty
Pictures: ASOS
For a casual date night in winter, you need to plan for comfort and style, and winter fashion is all about strategic layering. You’ve got to deal with it being cold outside but hot on the tube, and don’t get us started if you end up having to power walk to get to your destination. An oversized tailored coat will do all the work for you here – with olive greens and burgundy tones being your best bet this season. If you choose a quality wool style, you’ll be able to wear whatever you like beneath it because it’ll keep you warm no matter what. If you were wondering how to dress smart-casual this winter, loafers are the way to go, and you can up the overall comfort levels with soft knits and velvets, while still nodding to AW25 trends.
GET THE LOOK:
ARKET wool blend double breasted maxi coat in dark burgundy, £259
ASOS DESIGN longline jumper with funnel neck in mushroom, £30
