The holiday season brings about many occasions, including family parties, friend reunions, shopping galore, and an overall stacked social schedule. No matter where the season takes you, we’re here to ensure your wardrobe is fully equipped to handle whatever your holiday itinerary throws its way! More importantly, each look will have you feeling both stylish and warm throughout the winter months. Gone are the days when you had to choose comfort or style—we promise, you can have the best of both worlds.
From gift shopping to tree lot chopping to attending family gatherings and watching the ball drop, there’s a holiday look for every time, place, and location. We guarantee that you’ll be toasty and warm, styled to the max, and feeling your absolute best at every holiday festivity marked on your calendar. Read on to unwrap the holiday outfits that will keep you stylish and cozy throughout the season.
‘Fit for a Family Affair
A knit dress is the perfect solution for the multitude of family get-togethers the holidays bring. We love pairing a sweater dress with tall boots for the ultimate seasonal, cozy vibes. Especially when wearing a high-neck sweater, we suggest adding a statement ear cuff to bring a little extra personality to your look. Jenny Bird’s tubular style is a perfect standout piece all on its own—you may never want to take her off!
Dress to Shop ‘Til You Drop
The lead-up to the holidays usually includes lots of running about and shopping trips. You’ll want the utmost comfort without sacrificing style as you’re crossing off your to-do list! Power through your gift-giving era with a comfy sweatshirt (we love a style like One DNA’s motivational message), a classic trench for warmth, and a baseball cap to complete the look.
Tree Shopping and Chopping
If you’re one who opts to place a festive tree in your home during the holidays, we have a look that gives “Christmas Tree Lot” waiting for you. Fashion-forward and weather-resistant boots, a puffer vest, and a warm knit will have you in the spirit to find the perfect tree to bring home for the holidays. Finish off with a hands-free crossbody bag and you’ll be good to go.
The Dinner Party Host
Say hello to truly classic dressing for a classic occasion. You can never go wrong in an all-black, minimally chic outfit. Tove’s Riley dress is the dream of all little black dresses with a length that provides extra comfort for chillier weather. Modernize the look with open-toe heels and sheer tights (we promise; once you try this style hack, you’ll never look back). Finish off by adding in your favorite gold earrings or go sans jewelry for full-on minimalism—it’s the dresser’s choice.
Inspired by Lady Di
Forever an icon, the late Princess Diana’s style archives hold timeless fashion inspiration. As an ode to Lady Di this season, invest in a chic matching set in a bold colorway. Don’t forget the XL statement earring—the perfect pair is key to complete the look. Finish your ensemble with a pair of sheer tights, slingbacks, and a top-handle bag.
Tonal Pattern Play
There’s fun to be had even when sticking to one colorway. Playing with textures, patterns, and prints while staying within a tonal color palette gives a new take on monochromatic dressing. While plaid is a festive seasonal favorite, pairing the print with luxe knits and form-fitting base layers gives the pattern we all know and love a fresh perspective. Having a layered sweater and turtleneck adds an extra element so that the patterned pants become an accent, rather than take over the entire look.
For Outdoor Festivities
If you’re attending any outdoor festivities this season, rest assured that you can remain bundled and stylish at the same time. Balaclavas are winter’s must-have cold-weather accessory. Pair yours with outerwear in a coordinating color for a sleek and sophisticated finish. Throw on a pair of sunnies to complete the look if you’ll be braving the cold during daytime hours.
The Party Doesn’t Stop
For a comfortable dressed-up holiday party look, try a sweatshirt paired with party boots. It’s the combo you never knew you needed. When playing with colors, a cool, icy lavender is the perfect shade for the holidays without being too literal. Plus, it’s a hot color for this season. When worn with statement shoes like Brother Vellies glitter boots (How amazing are they, though?!), you have the ideal balance of worlds. Throw on a cute accessory like Don’t Let Disco’s stardust bracelet to complete this alternative holiday vibe.
Lounging in Luxe
If you’re home for the holidays, lounging in the living room can still be styled in luxe. Rather than a sweatsuit (though we have nothing against our fave hoodie), reach for a cashmere maxidress. Think of this style as the elevated sister to a nightdress but made for daytime wear. Pair with a sleek pair ofslippers for a dreamy look that can be worn in or out of the home. We highly suggest finishing off the look with standout jewels. We love Eriness’s two-stone eternity band as a pop of color to complete the outfit.
Whether dressed up or down, her collection of colorful, stackable bands is perfect for jewelry lovers to play with.
Western Meets Holiday Glam
Modern takes on western style have become more popular season after season. The holidays are an ideal time to play with western glam in a subtle yet stylish way. Staud’s cult-fave Wally boots have received a western twist this season and are the perfect shoes that have just enough western flair. Style with a shimmering minidress and a fringe handbag for a festive western glam look.
Sleek and Chic
For daily dressing to and from the office, gift shopping, and errands galore you’ll need a solid look that serves multipurpose style. You can never go wrong (or get too chilly) in a leather trench, a go-to pair of denim, and a classic turtleneck. The best part about this look is that it’s transitional. Throw on sneakers for running out and about or a sleek pair of boots for casual occasion dressing.
A Very Stylish New Year’s Eve
When ringing in the New Year, you don’t have to comprise comfort (or your body temperature) for style. ICYMI, sequin skirts have been topping the list of most-wanted party styles this season. There’s no better way to take on the trend for winter than with a chic maxi length. We recommend balancing the skirt with a black blouse and completing the look with a cute statement bag like this fuzzy JW Pei one we’re obsessed with.
A Monochromatic Moment
The chicest way to channel the holiday spirit (without channeling jolly old St. Nicholas) is with a well-designed cashmere set. The key here is to really own the monochromatic moment. In terms of footwear, we suggest avoiding white or cream tones and sticking to darker colors like black or brown. From gift-wrapping marathons to home decorating, we promise you’ll want to live in this all season long. Comfort and sparking holiday joy? It’s the magic of the season.