Skip Nav

POPSUGAR / paid for by / Very


Winter Outfit Ideas 2020

Behold: Outfit Inspo For All Those Upcoming Winter Activities

We've partnered with Very to help you celebrate seasonal moments in style.

Let's face it: winter events are going to look a little different in 2020, but that doesn't mean they shouldn't be celebrated! To help you embrace the end of the year in style, we've tapped three influencers — Berry Malinowska, Tasha Green, and Simone Powderly — to share how they're reinventing their own approach to fashion for upcoming seasonal moments.

Whether it's a cosy-glam outfit for a virtual Christmas gathering or a warm and functional outfit for a quiet trip to the countryside, they've got outfit recommendations in spades for every party, occasion, or weekend outing you've got planned. No matter what the season brings, their picks will inspire you to have fun with fashion — or at the very least, give your joggers a break!


A trip outside the city for a day or two is a fun way to escape the monotony of staying at home, enjoy the season, and explore something new. You'll undoubtedly want to be in something functional and comfortable for the journey, but Berry suggests having a little fun with your outfit as well.

"Printed wide-leg trousers and a cardigan is a perfect cosy (and comfy) combination that is sure to keep you warm while maintaining a dressed-up feel, whether it's for exploring nature or simply enjoying a glass of wine by the fireplace. I'm a big fan of animal prints (especially zebra!), however, for winter, I like to tone them down with neutral tones and cosy fabrics like the textured baker boy hat or a knitted cardigan."


Birthday, engagement, or even "just because" celebrations may be more virtual and intimate these days, but a party still deserves a party outfit. Take notes from Tasha and turn to your most statement-making pieces. Bonus points for anything with feathers.

"Nothing says cocktail party more than flamboyance, and that's why I like to go with feathers — what a fun way to do a festive get-up! A statement top and boots and a long, flowy skirt is the perfect party outfit. All the items are so comfortable and allow you to let your hair down without having to worry about any slip-ups!"


If you're celebrating a Zoom Christmas like Simone is doing with her girlfriends, follow her lead and opt for cute on top and cosy on bottom.

"This outfit is cosy but keeping it cute! You can dress this up with a few accessories and a little lipstick. UGG boots (yes — the ultimate comfort) complete the look so you can take your cute pics. I love the style and colours of the outfit, and it's perfect for those who don't like the traditional Christmas colours."


The party may be online, but half the fun of ringing in a new year is getting all glammed up. Berry's tip? Whip out your festive finest, and don't skimp on the style.

"Celebrating at home doesn't mean we shouldn't pull out our best outfits! Funky accessories with the bright satin midi feel super fun while also festive, making this the perfect outfit for your virtual celebrations. I love the satin midi as it can feel super glamorous with sparkly accessories but can also be repurposed for casual daywear with a pair of chunky boots."


The Christmas season doesn't come without a bit of family time, and with everything else going on, the last thing you want to be worrying about is whether Mum would approve of your outfit. Luckily, Tasha has a formula that's foolproof every single time.

"This outfit looks really put-together, but in reality, all you've done is thrown on a jumper with some trousers and accessorised well! The textures and tones of the outfit are what make it stand out even though technically you've barely made an effort — my kinda vibe! Faux leather trousers have recently become one of my staples — they are so versatile and can make even the most basic jumper look good. And I always love platform shoes as they make your legs look amazing and a lot longer!"


If you've got a socially distanced date night on the books, you can never go wrong with an easy, monochromatic look. As Simone notes, don't overthink it!

"Winter is all about comfort, but this outfit gives you that ultimate edgy style while keeping you warm and full of comfort. Date night makes me flustered, so a go-to outfit in all black is essential. You can't beat skinny, high-waisted jeans with a cute jumper!"

Credits: Associate Art Director: Samara Grossman; Senior Photo Producer: Alex Friedlander; Day-Of Producer: Joanne Lawless; Visual Designer: Mia Coleman