The holiday season brings a calendar full of occasions—each with its own dress code, vibe and opportunity to showcase your personal style. Whether you’re attending a chic holiday party, catching up with coworkers at the office fête or simply running festive errands around town, your outfit can set the tone. The key is finding looks that balance celebration with comfort, and statement-making moments with wear-again versatility.
Our Stylists curated a holiday outfit guide to help you dress for every occasion. We’re walking through the spectrum of style to prep your next festive Fix, from the “nicer” nights out to the more casual everyday moments, so you’ll feel confident and chic no matter where the season takes you. Let’s do it.
Cocktail Party Dressing
Cocktail parties are your chance to shine—literally. This is the moment to bring out those fabrics and details that feel unapologetically festive. Sequins, metallics, satin and faux leather instantly set the tone for a night of celebration. Stylist Erin adds, “Lean into rich cherry reds, forest greens and textures like suede or velvet—they say ‘party!’”
We’re obsessed with party pants this season—AKA pants featuring a “fun” element like faux leather, sequins or embellishments. Pair them with a sleek camisole and a great pair of heels you can dance in. Prefer a dress? Opt for a statement style. We love mesh, velvet, animal print or even solid black with hardware details. Then, add your favorite jacket (like a moto jacket or faux fur coat) and go-to heels (like strappy sandals or metallic heels).
“Lean into rich cherry reds, forest greens and textures like suede or velvet—they say ‘party!’”
-Erin, Stylist
Office Holiday Party Outfits
Office holiday parties call for a look that balances festive flair with professionalism. Think bold colors, luxe textures and polished silhouettes that keep you comfortable mingling with colleagues.
For a more daring take, try a bold blazer-trousers combo in a striking color or with some shimmer. Stylist Kate says, “Play with one standout piece and keep the rest simple. A jewel-tone blazer or metallic pleated skirt can bring festive energy.” If subtle sparkle is more your speed, reach for a fine-knit sweater with metallic thread or a plaid midi skirt paired with a knit. These looks say “celebratory” without crossing into overly casual or overly flashy.
“Play with one standout piece and keep the rest simple. A jewel-tone blazer or metallic pleated skirt can bring festive energy.”
-Kate, Stylist
Family Holiday Outfits
Family get-togethers often call for relaxed outfits that still feel special. This is the time for soft fabrics, pretty details and silhouettes that let you indulge in second helpings of dessert without worry.
A detailed blouse—whether embroidered, lace-trimmed or finished with subtle puff sleeves—pairs beautifully with dark denim or a slip skirt. “A knit sweater with a midi skirt is perfect. So elevated but really comfy!” Pair with ankle boots or ballet flats to keep it comfortable but polished.
“A knit sweater with a midi skirt is perfect. So elevated but really comfy!”
-Jackie Stylist
Winter Occasion Outfits
Whether you’re ice skating, visiting a holiday market or strolling through snowy streets, cold-weather activities require warmth and practicality without sacrificing style. Layering is the secret. Stylist Caro advises, “Stay warm without sacrificing style by starting with a sleek base: dark denim or tailored trousers with a cozy knit. Then, top it off with a statement coat.”
An option with a festive nod: Start with a novelty knit—a fair isle sweater or a turtleneck with sparkle—then build from there. Pair with denim featuring embellishments (think crystal accents or metallic hardware) or try corduroy pants for extra texture. If you love dresses, prairie-inspired midis are perfect layered under barn jackets or puffers.
Complete the look with weather-ready boots or sturdy sneakers, plus cozy accessories like a knit beanie or patterned scarf.
“Stay warm without sacrificing style by starting with a sleek base: dark denim or tailored trousers with a cozy knit. Then, top it off with a statement coat.”
-Caro, Stylist
Holiday Loungewear
Not every holiday moment calls for sparkle, but that doesn’t mean you can’t look pulled together while staying comfortable. From gift wrapping to dashing out for hot cocoa, lean into cozy matching sets and sporty layers.
An athletic matching set in seasonal hues feels instantly stylish. “Our ribbed knit lounge sets are the perfect outfit for cozying up by the fireplace and enjoying your favorite holiday movie,” says Stylist Jackie. For errands, pair leggings with a barn jacket or a puffer jacket. Finish with active or retro sneakers and add a quilted tote or baseball cap for an easy finishing touch.
“Our ribbed knit lounge sets are the perfect outfit for cozying up by the fireplace and enjoying your favorite holiday movie.”
-Jackie, Stylist
Get your wardrobe holiday ready
Want to upgrade your holiday wardrobe while simultaneously skipping the shopping chaos? Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or get special discounts when you keep 5+ pieces. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
