The Chic Holiday 2020 Outfits You Can Rewear All Year Long

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If you're looking for an excuse to splurge on a chic holiday outfit, then it's worth asking yourself if the pieces can be worn well after the proverbial party dust settles. While practicality is probably low on your list of priorities when it comes to finding a festive ensemble, if you plan to cash out on something luxe it's best to be sure that it will add value to your closet.

Between the months of Nov. and Jan. there are plenty of opportunities to get dressed up. And for those that have the means, splurging on a new item for your closet can actually be a sound investment — as Rebag's Clair Report (short for comprehensive luxury appraisal index for resale) proved, stretching the dollar in your wardrobe is as prevalent, and profitable as ever. "Bottega Veneta trades at about 38% of its retail price, an increase of 10% since 2019", founder and CEO of Rebag Charles Gorra explained in a video for the brand.

This means demand for the brand has rocketed in the last 12 months — and it isn't the only one. The secondhand luxury retailer's findings explain that even in the midst of a pandemic, shoppers are still spending more money on quality forever pieces, like bags and elevated accessories from powerhouse names like Louis Vuitton and Chanel. So when you're on the hunt for your Thanksgiving look for the living room, don't feel guilty if you're inclined to spend a little extra money on items you know will work hard in your wardrobe.

Whether you like dressing up for the holidays or prefer a cozier approach, all the inspiration you need over the course of the next few months can be found scrolling down your Instagram feed. Influencers, editors, and, yes, celebrities, too, are churning out a slew of looks that are well suited for all your seasonal obligations. Continue ahead for a compilation of some of the best looks on the market — with a selection of shoppable options to get you started.

We only include products that have been independently selected by The Zoe Report's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Holiday 2021 Outfits: Elevated Knitwear

Keeping in line with the overarching theme for 2020, if you plan to take a more laid back approach to dressing this holiday season, you can't go wrong with color-coordinated knitwear pieces. Minimalists will gravitate towards plain-colored pieces from LESET and go bananas for Source Unknown's cropped sweaters in the same breath. For those whose style calls for a bit more drama, Paloma Wool's highly coveted checkered pants are an easy choice — as they're currently going viral on Instagram. As far as styling goes, you'll want to accessorize with equally as luxe pieces to balance the casual feel.

Holiday 2021 Outfits: Midi Dress + Boots

Even if dresses aren't your thing, you'd be surprised at how having a few really solid styles in your arsenal will positively impact your closet. Aside from giving off an instantly polished feel, the one-step midi outfit can be both dressed up and down with ease (think sneakers and heels). Consider taking notes from model Imani Randolph and paring Ganni's fitted mesh dress back for the holidays with knee boots, keeping the accessories to a minimum to really allow the floral-print to speak for itself.

Holiday 2021 Outfits: Sleek All-Black Look

Kendall Jenner wore an all-black look from The Row out in New York City last week, and it's the perfect layered outfit for intimate holiday dinners. From the strategically layered turtleneck bodysuit to the unexpected corduroy pant and poplin shirt pairing for added dimension, the model makes a strong case for a sleek and simple look for formal occasions. To bring the outfit to the next level, just add a pair of sparkling chandelier earrings or a bold stack of vintage rings that will pop against the all-black color story.

Holiday 2021 Outfits: Oversized Layers + Tall Boots

Finding the balance between comfort and style is a lot easier when there's layering involved. Start with a pleated midi skirt that falls below the knee, paired with tall boots to leave very little skin exposed to the cold temperature. On top, go with long "shackets" (shirt + jacket) or printed cardigans layered over an equally slouchy pullover — Isabel Marant Etoile's checked coat is having a major moment right now

Holiday 2021 Outfits: Embellished Dress With Heels + Tights

Bringing in the new year from the comfort of your home doesn't mean that you shouldn't put on a dressy look to mark the occasion. Opt for a semi-sheer sequined slip like cult shoe designer Amina Muaddi. Prada's vintage plunging dress on 1stDibs is made for the occasion. Have a pair of ornate sandals you can't wait to wear when the weather breaks? Add any one of Calzedonia's Italian-made tights into the mix to combat the winter chill.

Holiday 2021 Outfits: Festive Sweater + Jeans Look

One of the best things about denim is that it has the duality to be worn both running errands and to virtual holiday parties, alike. For the latter, it's important to style your jeans with especially festive pairings to give them a dressier vibe. Rowing Blazer's Princess Diana-inspired sheep sweater is a prime example of a statement crewneck that can be worn well into 2021. Go the extra mile and embrace one of the biggest trends out of Copenhagen and accessorize with a detachable bib collar to ensure all eyes will be on you during your Zoom-call holiday gatherings.