Unless otherwise specified, all sizes in this post are listed in women’s.
1. An elastic-waist woolen A-line skirt for anyone whose cold-weather wardrobe consists of jeans, jeans, and more jeans. This skirt will still keep you warm while giving your go-to looks a refresh.
2. These investmentworthy Spanx faux-leather leggings that you can style a million different ways, which will hopefully distract anyone from noticing when you end up wearing them days in a row. They just look good with everything!
3. A long-sleeve mock turtleneck bodysuit if you're looking to pack pieces that can work double duty as a standalone style or a chic layer under a sweater, sleeveless dress, or your favorite jacket.
4. A cropped button-up cashmere sweater because you're going to need to employ some strategic layering to make it through a whole gambit of holiday visits where the house temperatures range from a sauna to the North Pole.
5. A flowy tiered shift dress to achieve max comfy-cuteness whether you're holiday party-bound or just headed out for a winter stroll.
6. A stunning sweater midi dress so you can prove all those people wrong who told you wow-worthy evening wear can't be comfortable.
7. A super cozy knit jumpsuit with stretch for days that makes the perfect travel companion for long car rides or flights where comfort is key. Plus, it'll feel pretty good sipping cocoa by the fire in this, too.
8. A trendy pair of round sunglasses that comes with a protective hard case because you're not trying to crush another pair of stylish sunnies in your carry-on bag.
9. An oversized houndstooth sweater-vest if you're looking for a mix-and-match way to punch up the outfit you've already worn three times since you've been home.
10. A cropped padded sports bra because suitcase space is at a premium and this is a sports bra and casual top all-in-one.
11. A long-sleeve tie-waist dress to add a whole lot of waist-cinching va-va-voom to your standard knit dress lineup.
12. A pair of incredibly versatile high-waisted leggings so you can lounge, work, workout, and go out all in the same pair of super soft, stylish, and stretchy leggings.
13. A pair of slip-on sneakers for a go-with-everything style that will see you through airport security lines, holiday shopping, and more with a cushy memory foam sole your tired feet will appreciate.
14. A faux-suede miniskirt that'll be your reliable sidekick for festive dinners, holiday parties, and whatever else your end-of-year social calendar has in store.
15. A knit long-sleeve sweater dress with a colorful pleated panel if you're in need of a showstopping number that'll make you feel like the main character in a dreamy Hallmark movie all night.
16. A pack of knit over-the-knee socks because all those dresses and skirts you packed aren't going to winterize themselves! Don't worry, these babies got some stretch so they can accommodate a wide range of sizes.
17. A pleated midi skirt to wow the crowd in a notice-me shade of vibrant metallic. Bonus: the pleats will hide any wrinkles it accumulated sitting in your suitcase.
18. A satin pleated top so you can easily dress up the single pair of black leggings you plan to wear as pants for the duration of the holiday season with a compliment-catching style.
19. A pair of thick *sherpa*-lined joggers for winning the award for "most cozy" whether you're on a chilly flight or wrapping presents in your parents' chilly basement.
20. A pair of Ugg ankle boots that can play the part of supportive slippers or cozy going-out shoes with equal success. They've got all the comfort you've come to know and love from Uggs in a shorter style that won't weigh you down.
21. A super versatile bodycon jumpsuit if you want a holiday party outfit that wows, but that you can rock the rest of the year, too.

