31 Outfits To Close Out 2020 On A High Note

Originally Published: 
Darrel Hunter

Now that 2020 is (finally!) coming to an end, the next 31 days are your last chance to pull out all the stops and try the trends you've long admired from afar. You'll need an arsenal of cute winter outfits this December to get you through dark dreary days and festive (social distancing) holiday parties alike. But the good news is that cozy and celebratory aren't mutually exclusive terms. You can stand out in a sweater just as easily as you can in sequin pants.

To exemplify that fact, you'll find a range of 31 outfits worthy of testing this holiday season. Some are meant for you to throw together on days when it's too cold to do much more than curl up on your couch. Others offer ways to take winter layering up a notch — adding in the season's bold color trends, swapping wool for slick leather, and even styling practical footwear in a way that feels fancy. If there's any time of year where fashion is meant to be celebratory and fun it's now through New Year's Eve. Find all the inspiration you'll need for both work and play below.

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Cute Winter Outfit: Put Together A Monochromatic Ensemble

Fight the gloom by opting for a bright, layered-up ensemble.

Cute Winter Outfit: Combine A Winter Look With White Tights

While black tights may be the usual pick, white ones are a surprisingly chic alternative to style with loafers and a quilted coat.

Cute Winter Outfit: Wear Pajamas With A Coat

Dress up cozy, daytime pajamas with a luxe statement coat.

Cute Winter Outfit: Warm Up Your Look With A Quilted Jacket

For those in balmier climates, considering finishing off light wash jeans and boots with a quilted jacket.

Cute Winter Outfit: Swap In Velvet Suiting

The time has come to swap out your fall suiting for richer textures like velvet and wool.

Cute Winter Outfit: Dress Up In Prints

Instead of opting for the usual sequins for holiday events, try a bold pattern to stand out from the crowd.

Cute Winter Outfit: Keep It Simple With A Boiler Suit

Not feeling particularly excited about getting dressed at the moment? Layer a turtleneck or plain tee under a boiler suit and your ensemble is done.

Cute Winter Outfit: Embrace Metallic Dresses For Evening

If you're ready to try the season's best metallic looks, try styling a long sleeve dress with tights. Boots add a more laid-back effect while pumps are fancier.

Cute Winter Outfit: Opt For Practical Footwear

A hiking or snow boot can be an unexpectedly cool choice with a casual outfit.

Cute Winter Outfit: Pull Together An All White Ensemble

Embrace the snowy weather by wearing an all white look. Mid-calf boots tucked into coordinated trousers look instantly polished.

Cute Winter Outfit: Swap A Dress For Party Pants

If you want to try an alternative holiday celebration look, try switching out a dress for high-waisted trousers and a printed jacket.

Cute Winter Outfit: Mix Chic Separates With Sneakers

Have fun with your wintery looks. Try adding pops of color and a fun pair of sneakers to liven the mood.

Cute Winter Outfit: Tie A Sweater Around Your Waist

Get creative with layering and try tying a sweater or sweatshirt around your waist, cincing in a bulky coat.

Cute Winter Outfit: Bring Back The "Groutfit"

A few years ago, "groutfit" or an all-grey outfit became the look to try. Now, bring it back in a modern way with loungewear, jewelry, and a pastel bag.

Cute Winter Outfit: Dress Up A Casual Look With A Trench Coat

To instantly add polish to a casual outfit, throw on a tailored trench coat.

Cute Winter Outfit: Build An Outfit With Unexpected Layers

A printed turtleneck makes a summery dress seem like a reasonable choice for cold weather.

Cute Winter Outfit: Layer Leather Into Your Look In Unexpected Ways

Instead of a standard moto jacket, try finding new and creative ways to add leather into your look. A sleek blazer or wrap top feel especially fresh.

Cute Winter Outfit: Wear A Sweater Vest With Leather Pants

Sweater vests are an essential layering piece this season. Layer yours over a button-down with cool leather trousers below.

Cute Winter Outfit: Break Up Neutrals With Texture

Bring intrigue to a neutrals look by mixing in snake skin or other luxe textures.

Cute Winter Outfit: Finish Your Look With A Statement Coat

Since your coat is most of what people will see as you navigate the streets, try a statement coat as your final layer.

Cute Winter Outfit: Try A Sweater Dress

Try a sweater dress instead of your usual day-off sweats.

Cute Winter Outfit: Pump Up A Look With Platform Boots

Platform boots are a fashion-insider favorite this season. Try styling yours with a cozy skirt and sweater.

Cute Winter Outfit: Dress Up With A Glittery Top

To instantly dress up your outfit, try swapping a blouse for a sequin bodysuit.

Cute Winter Outfit: Layer Your Tops

Don't retire your favorite summer tops. Instead, layer with a long sleeve tee and puffer jacket.

Cute Winter Outfit: Go For Head-To-Toe Leather

Leather (or faux) head to toe doesn't have to make you feel like you're in the matrix. It can offer a polished take on suiting.

Cute Winter Outfit: Embrace Classic Plaid

Plaids are a staple this time of year. Opt for a mute color palette and style with light separates for a more polished take.

Cute Winter Outfit: Layer A Puffer Creatively

Puffers don't have to be super casual. Try layering with more elevated separates for a dressed up and cozy take.

Cute Winter Outfit: Swap Trousers For Wide Leg Denim

Not only is wide-leg denim a cool alternative for trousers, it's also ideal for layering your heat tech underneath.

Cute Winter Outfit: Embrace Bold (Faux) Fur

These days, there are a number of brands making cool, eye-catching faux-fur coats. Make one the focal point of your look.

Cute Winter Outfit: Ditch Your Mini Bag For A Sleek Tote

In winter you're often stuck lugging around any number of necessary accessories — gloves, earmuffs, and beanie included. Swap a small bag for a tote that can hold them all.

Cute Winter Outfit: Dress Up Your Sweats

Dress up your loungewear with a sleek wool pinstripe coat. Keep the look casual by finishing off with sporty sneakers.

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