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Unless otherwise specified, all sizes in this post are listed in women's.
1. A pleated midi dress is the perfect piece if you have an endless stream of events to attend this season. It'll look just as great at a work holiday party as it will at an intimate NYE celebration!
2. A velvet headband that will instantly make any outfit festive — even if you are wearing all black.
3. A pair of straight slacks to make it look like you're wearing the bottoms of a suit without dropping some serious cash. You can go the preppy route with these and pair 'em with a frilly blouse, or tuck your favorite band tee inside for a ~chill~ vibe.
4. A very chic blazer that is as versatile as it is cute. You can wear this over a bralette and glitzy shorts when going out with your friends, or wear it with a silk blouse and trousers during an office holiday party.
5. A smocked peplum top, because 'tis the season of joy — and that extends to your outfits! This shirt has the perfect palette if you want to rock a green-and-red look, but feel more comfy in pastels.
6. A ribbed knit dress ideal for fancy dinners, and here's why: It's cozy enough to wear for extended periods of time while looking chic enough to serve looks on the 'Gram.
7. A ruched bodycon dress, because holiday parties don't just include sipping on eggnog around a fire — they also include those fun get-togethers with old friends! This dress will take you from an intimate dinner to a club to an after-party seamlessly.
8. A faux fur jacket that serves as proof that keeping warm and cozy can look very stylish.
9. A scuba midi dress, because you'll need something to wear to every winter wedding you have this year. This is also the perfect dress for any winter occasion, whether you're showing up to your work's NYE party or are attending a chic holiday soiree.
10. An open-front chiffon cardigan with a gorgeous pattern that'll go with anything! It's perfect for those days where you can't be bothered to switch out of your leggings and cami (#HostingLife), but still want to look like you put in tons of effort.
11. A pair of patent leather Mary Jane shoes, because flats are back, and mood boards are ripe with the following outfit formula: these shoes paired with bright red tights and an LBD. These shoes will remain comfy throughout the evening, and can work with your daily wardrobe, too!
12. A holiday sweater that's anything but ugly. This is really the perfect sweater for any occasion — you can throw it over your shoulders if you get chilly at a fancy event, or wear it during your annual reunion with your hometown friends!
13. A Peter Pan dress, because 'tis the season of dressing like a present! This is perfect for a sweet Mod look — just pair this with fluttery lashes and your favorite knee-high boots.
14. A tie-waist dress if you have a full day planned with no time for outfit changes. This is the go-to dress if you need something you can run around town in while still looking chic enough for a fancy dinner with your fam.
15. An off-the-shoulder textured blouse that'll cause everyone to know what "slay" means by the end of the night. This is a showstopper piece and will take very little zhuzhing (AKA, you can just wear this with pants and walk out the door) to look amazing.
16. A cozy cable knit sweater, because — do we have to explain this one? There's nothing more classic than a solid sweater for the holidays, and this will pair perfectly with slacks for the festivities *plus* jeans or leggings throughout the rest of the winter season!
17. A velvet dress with a cute square neck so that you can ring in the festivities with a cute Winter Wonderland aesthetic. Pair this with semi-sheer tights and pointed toe heels for a chic holiday party look.
18. A pair of drop earrings, because globby metallic jewelry is all the rage these days! These are perfect for adding a '90s minimalist edge to your outfits while staying on theme with the white-and-gold holiday decor vibes.
19. A rosette satin mini dress that'll make you the fun belle of the ball. This is great if you want to add bright vibes to your look, even if the event you're attending is a black tie sort of thing.
20. And a pair of flared pants, because your love of retro outfits deserves some limelight during the season. These pants will look killer with platform boots and your favorite frilly blouse!
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