I have a confession to make. Every year around the middle of November I start planning my December outfits like it’s a full-time job. My sister thinks I’m a little ridiculous about it, and honestly, she’s not wrong.
But there’s just something about the holidays that makes me want to dress up more than usual. The lights, the music, the excuse to wear velvet in the middle of the day. Who could resist?
So this year I finally sat down and pulled together all my favorite looks, from the cozy stay-in kind to the sparkly dinner party kind.
20 Holiday Looks I’m Wearing on Repeat This Season
Velvet Christmas Dress With Knee-High Boots
Velvet is the fabric of the season, and I will not be taking questions about that.
A deep burgundy or forest green velvet dress paired with tall leather boots is my go-to for basically any December event where I need to look like I tried.
White Knit Dress With Camel Coat
There is something so calm and pretty about a white knit dress in December. It reads as festive without shouting about it.
Throw a camel coat over the top, add some simple gold jewelry, and you have a white christmas outfit that works for a lunch, a coffee date, or a low-key family gathering. I wore something almost exactly like this to my aunt’s holiday brunch last year and got compliments the entire time. The camel and white together is just such a soft, warm combination.
Cable Knit Sweater With Plaid Skirt
Now this is the preppy holiday look of my dreams. A chunky cream cable knit sweater tucked into a plaid skirt, with tights and loafers or little ankle boots.
It feels like something out of an old catalog in the best way. My friend Dana wears this exact combo every single December and she looks put-together every time. So of course I copied her.
Ralph Lauren Cable Knit And Tartan Skirt
If you want to lean all the way into that classic, timeless feeling, this is your look. A crisp cable knit paired with a tartan skirt is basically the definition of holiday polish.
A ralph lauren christmas outfit built around these two pieces will never go out of style, which is exactly why I keep coming back to it. Add pearl earrings and a pair of loafers and you are set for everything from a church service to a nice dinner out. In fact, I think this might be my favorite one on the entire list.
Cream Turtleneck With Satin Maxi Skirt
So here’s a formula that never lets me down: a cozy top on the upper half, something a little dressier on the bottom. A fitted cream turtleneck with a long satin skirt in beige or gold tones is elegant AND comfortable, which is my favorite kind of outfit.
Red Bow Mini Dress With Ballet Flats
A little red dress with a bow detail is such a fun, playful choice for the holidays. And pairing it with ballet flats instead of heels keeps it sweet rather than serious.
Red is one of those colors that just always looks festive without any effort. Add sheer tights and a coat and you’re ready for anything. This is the one I’d pick for a party where I know I’ll be on my feet all night.
White Faux Fur Coat With Knit Dress
Okay, this one feels like a movie. A soft white faux fur coat over a simple knit dress is glamorous in a way that doesn’t take much effort at all.
The coat does all the work here. You could wear the most basic dress underneath and still look like you’re about to step out of a snowy carriage. I don’t own the coat yet but it’s absolutely on my list, and my husband knows better than to be surprised when it arrives.
Fair Isle Sweater With White Jeans
Winter white jeans are underrated and I will keep saying it until someone believes me. Pair them with a patterned Fair Isle sweater and you have a look that’s casual, warm, and still very much holiday-appropriate.
This is my errand-running, tree-shopping, hanging-around-the-kitchen outfit. Add some duck boots or clogs and you’re good to go. It’s cozy without being sloppy, which is the sweet spot in December.
Emerald Velvet Dress With Gold Heels
Emerald green in velvet is just STUNNING. There’s really no other word for it. It’s rich and jewel-toned and feels expensive even when it isn’t.
Pair it with gold heels and gold earrings and you’ve got a look for the fanciest event on your calendar. I bought a dress like this on a whim two years ago and it’s become the piece I pull out whenever I want to feel a little bit special. Sometimes an impulse buy really pays off.
Cozy Knit Set With Shearling Boots
Not every December moment calls for a dress, and I fully respect that. A matching knit set, top and pants in the same soft color, is the definition of comfortable.
Add shearling-lined boots and you have a cozy christmas outfit that’s perfect for opening presents, drinking cocoa, and refusing to leave the house. This is what I live in on Christmas morning, and I wouldn’t have it any other way.
Christmas Lights Date Night Outfit
My husband and I have a little tradition where we drive around and look at the decorations every December, and I always want to look cute even though we barely leave the car. A christmas lights outfit needs to be warm but photogenic, because you know there will be photos.
I like a red sweater, dark jeans, a long coat, and a knit hat. Simple, warm, and it looks lovely with twinkling lights in the background. The trick is layers you can take off once the car heats up.
Ralph Lauren Blazer With Dark Wash Jeans
A structured blazer instantly makes any pair of jeans look dressy. It’s a trick I use all year, but it works especially well for the holidays when you want something between casual and formal.
Pair a navy blazer with dark wash jeans, add a silk top underneath and some loafers, and you’re dressed for a work party or a nice dinner without overthinking it. This is the outfit I recommend to my sister every single year when she panics about what to wear.
White Sweater With Burgundy Midi Skirt
Burgundy is such a beautiful color for December, deep and moody and rich. Pair a soft white sweater with a burgundy midi skirt and you get contrast that feels intentional.
Tuck the sweater in a little at the front, add tall boots, and you’ve got a look that carries you from afternoon to evening. I love that this one photographs well too, which matters more than I’d like to admit around the holidays.
Chunky Knit And Wide-Leg Trousers
Wide-leg trousers are having a real moment and I’m so glad about it. They’re comfortable, they’re flattering, and they look great with a big chunky knit tucked into them.
This is a good office-party option if your workplace is the kind where you don’t want to overdo it. Neutral colors, good shoes, and you’re done. Comfortable AND polished, which honestly is the whole point of getting dressed in December.
Plaid Coat With White Turtleneck Dress
A statement plaid coat can turn even the simplest outfit into something special. Wear a plain white turtleneck dress underneath and let the coat do the talking.
Plaid is so classically festive, and it reads as holiday without any red or green at all. I like this one for those chilly outdoor markets where you’re wandering around with a warm drink and looking at ornaments you don’t need but might buy anyway.
Sparkly Red Mini Dress With Tights
Every December calls for at least one sparkly moment, and this is mine. A red mini dress with a little shimmer to it, paired with opaque tights and heels or boots.
The tights make it wearable in the cold and keep the whole thing from feeling too summery. This is my New Year’s leaning look, honestly, but it works for any party where you want to catch a little light when you move.
Cream Cardigan With Slip Dress
A silky slip dress feels a bit bare on its own in winter, so I always layer a soft cream cardigan over the top. It’s such an easy way to make a delicate dress work for cold weather.
Button it partway or leave it open, add some simple flats or boots, and you have something that feels both relaxed and pretty. This is a great one for a quieter gathering, the kind where you want to be comfortable but still look like you made an effort.
Oversized Knit With Leggings And Boots
Sometimes you just want to be warm and cozy and not think too hard. That’s what this outfit is for. A big oversized sweater, comfortable leggings, and tall boots.
It’s the outfit I wear for travel days during the holidays, or lazy afternoons at my mom’s house. Not fancy, not trying to be, and completely perfect for the occasion. Add a scarf and you’re set.
White Monochrome Winter Outfit
There is something so striking about dressing head to toe in one color, and winter white does it beautifully. White pants, a white sweater, maybe a cream coat over the top.
It looks crisp and fresh against all the dark winter weather, and it feels a little bit like a fresh start, which suits the end of the year. Just be careful around the gravy at dinner. I speak from experience.
Cashmere Sweater With Satin Trousers
And here’s my last one, the look I’d wear if I could only pick a single outfit for the entire season. A soft cashmere sweater tucked into flowing satin trousers.
The mix of textures is what makes it. Cozy knit on top, that gorgeous drape of satin on the bottom. Add heels and gold jewelry and you look effortlessly done, even though you’re basically wearing the most comfortable clothes in your closet. I think that’s the whole trick to December dressing, really.
