Holiday Outfit Ideas
Finding a festive balance between celebratory and overdone.
Thinking about outfits this time of year feels different. Colder temps, more occasions, and a desire to simply acknowledge the shift in season calls for color, texture, and choices that feel celebratory but not overdone.
There’s nothing I dislike more than buying something I’ll only wear once. My approach to holiday dressing is practical: reworking pieces I already love, layering in a few thoughtful additions, and playing with timeless themes.
At the start of every season, I pull everything onto a rolling rack and spend an afternoon experimenting with outfits. It’s a ritual that helps me see what I already have, where the gaps are, and what combinations feel good for the rendezvous ahead.
I’m a big believer that creativity thrives with restraints — you can always work with what you already own to create something that feels good. This season, here are five ideas I’m experimenting with.
1. Fair Isle Sweater
I splurged on this Fair Isle sweater last month and I’m absolutely obsessed. If you’re thinking about trying it, size up — I rarely order mediums, and I’m so glad I did. The slightly oversized fit gives it a cooler, more effortless vibe. It works with everything: denim of any wash, leopard, tan cords, and even a pink silk skirt I never expected to pair with it. For accessories, I love it with chunky vintage rhinestone earrings, and if you need cozy basics, the Gap cashsoft socks are an easy yes to wear with boots. I’ve also been getting so much unexpected wear out of this cream belt, even in winter!
2. Red Pants
I’ve had these red J.Crew pants (similar here) since 2018, and I still love them. Pieces like this are the best reminder of why timeless classics are worth investing in. One of my favorite ways to style them is with a cream cashmere sweater — the leopard scarf (mine is old J.crew but similar here) adds just the right amount of texture and interest. I’ve been dreaming of a vintage Hermès cashmere scarf and have officially added it to my 2027 manifestation list. And you really can’t ever go wrong with a red, grey, and black combo. Sparkly socks and earrings make the look feel seasonal.
3. Red Sweater
This oversized v-neck from Reformation is a couple of years old, and they just brought back the cherry red. I love the fit and the slightly sportier vibe it has. I always pair red with medium or dark denim, but it also looks great with tan cords. And red with gold jewelry or chocolate brown always feels so rich and elevated — what do you think? This cashmere jacket was a vintage Max Mara find on The Real Real this past summer and the dainty layered necklaces are also vintage.
4. Festive Top
I found this vintage Pucci turtleneck on The RealReal at the end of last season and I adore the bright stripes and lurex. It feels playful and bold, and I love wearing it with a vintage belt and fun vintage earrings (these hearts are 90s Liz Claiborne). The Doen cranberry ruffle top has been a go-to this fall, and feels elegant styled with a vintage silk scarf—I love a rich winter floral (this Chanel one is so pretty too). These jeans in Valley View wash are great for boot and party season.
5. Statement Pants
There’s nothing better this time of year than festive pants that are also comfortable. I’ve had these En Saison velvet pants for years now and have styled them a bunch of different ways but I think my favorite is with black. The Sézane printed pair was an immediate yes — I know they’re going to be versatile across seasons and work with so many neutrals. I sized up to a 4 and the fit is perfect for both boots and ballet flats. And somehow I have a vintage pair of blue crystal earrings that match them exactly….meant to be. My fuzzy sweater is from my S&S days but here is a fresh option.
Wishing you a season where your style, and the way you show up, feels true to you!
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All of your party pants are so fun!