Every year around the first week of December my sister texts me the same question. “What are we wearing?” And every year I pretend I haven’t already thought about it, when in fact I have a running list in my phone that started sometime in October.
The holidays come with SO many little events. A late morning gathering with cinnamon rolls and coffee or a fancy sit-down dinner. That thing at the office where everyone stands around a folding table trying to look festive. It’s a lot of outfits guys!
So I put together this list for both of us, and now for you too.
20 Festive Looks I Come Back to All December Long
Red Velvet Dress With Slingbacks
There is nothing that says December quite like a red velvet dress, and I will not be talked out of it. The velvet catches the light in a way that just feels seasonal and a little bit special.
I pair mine with a low slingback so I can stand around chatting for hours without my feet staging a revolt. My favorite Christmas brunch outfit is exactly this, honestly, because it looks like effort without actually being much effort at all.
Tartan Skirt With Cashmere Sweater
Tartan is one of those prints that shows up every December and I welcome it back like an old friend. A pleated tartan skirt with a soft cashmere sweater tucked in is cozy and put-together at the same time.
Add tights and ankle boots and you have something that works for a chilly morning. My friend Dana wore this to my house last year and I complimented her on it about four times before noon.
Sequin Midi Skirt With Turtleneck
A sequin midi skirt sounds like a lot for daytime, but pair it with a plain black turtleneck and suddenly it reads as tasteful rather than over the top. The sweater calms the sparkle down.
I love this because you can wear the same skirt to something fancier at night and just swap the top.
Burgundy Suit With Satin Camisole
So a matching suit is my little secret weapon. A burgundy suit with a satin camisole underneath feels polished, feels intentional, and takes exactly zero brainpower to assemble because the pieces already match. This one is my go-to holiday party outfit when I want to look like I have my life together.
And the beauty of a suit is you can split it up later. The blazer goes with jeans, the trousers go with a knit. Very good value, in my opinion.
Emerald Dress With Velvet Heels
Emerald green is such a rich color for the season, and I don’t think it gets enough love next to all the red. A simple emerald dress paired with velvet heels looks luxurious even if the dress itself was reasonably priced.
Velvet shoes are one of those small touches that make a look feel very December. I keep a pair by the door all month.
Satin Blouse With Tailored Trousers
Not every event calls for a dress, and honestly some mornings I just want to wear pants. A satin blouse tucked into tailored trousers is elegant without trying too hard.
The satin does the fancy work, and the trousers keep it grounded. This is a great holiday hosting outfit because you can move around, refill coffee, greet people at the door, and still feel nice about how you look in the photos.
Crystal Cardigan With Black Midi Skirt
A cardigan with crystal or beaded buttons is such a sweet, old-fashioned kind of festive. I love it. Pair it with a black midi skirt and you have something that your grandmother would approve of and your niece would want to borrow.
It’s cozy and sparkly at once, which is exactly the mood I’m going for in December.
Chocolate Knit Dress With Gold Earrings
Brown is having a moment and I am fully on board. A chocolate knit dress is warm, flattering, and a nice break from all the bold jewel tones you see everywhere this time of year.
Add gold earrings, big ones, and you’re done. I wore this to a low-key morning gathering last year and felt comfortable the entire time, which for me is the actual goal.
Red Sweater With Satin Maxi Skirt
Here’s a combination I fall back on again and again. A chunky red sweater on top, a flowing satin maxi skirt on the bottom. Cozy up top, fancy down below, and the mix of textures is what makes it interesting.
The satin catches the light and the sweater keeps you warm, so it’s practical too. My sister stole this idea from me and now we have to text each other before events so we don’t show up as twins.
Velvet Blazer With Trousers
A velvet blazer is one of those pieces that does a lot of heavy lifting. Throw it over a simple top with trousers and instantly everything looks dressed up.
This has become my favorite corporate holiday party outfit because it’s professional enough for people you work with, but the velvet adds a festive touch so you don’t look like you wandered in from a Tuesday meeting. Of course, a good blazer is worth spending a little more on.
Bow Blouse With Wide-Leg Pants
A pussy-bow blouse (the kind with the ties at the neck) is so charming and a little bit vintage. Tuck it into wide-leg pants and you have a look that’s super romantic.
I love how the bow gives you something going on at the neckline so you barely need jewelry. Less to think about in the morning, which I always appreciate.
Silver Sequin Top With Black Trousers
Silver sequins feel very much like the season, all frosty and bright. A silver sequin top with plain black trousers keeps the sparkle up top where everyone can see it and keeps the bottom half simple.
This is my failsafe office holiday party outfit, because it’s festive enough to feel like you made an effort but not so much that you outshine, well, everyone. Balance.
Ivory Satin Dress With Burgundy Pumps
An ivory satin dress feels so soft and pretty against all the deep December colors. On its own it might read a bit bridal, so I like to anchor it with a rich burgundy pump.
The contrast between the pale dress and the deep shoe is what makes it feel intentional. Add a small clutch in the same burgundy and it looks like you planned it for weeks, even if you threw it together in ten minutes.
Embellished Jacket With Pencil Skirt
An embellished jacket, the kind with beading or a little shimmer worked into the fabric, is a statement all by itself. Pair it with a plain pencil skirt and let the jacket be the star.
This works so well for a holiday party outfit when you want something structured and grown-up rather than flowy. In fact I think structure photographs beautifully at evening events.
Plaid Midi Dress With Knee Boots
A plaid midi dress is cozy and countryside-charming, and I mean that as the highest compliment. Add tall knee boots and you have something you could wear to a morning gathering and then straight out for a walk after.
I love an outfit that lets me keep moving. This one is warm, it’s forgiving after a big meal, and it just feels like the season.
Feather-Trimmed Top With Tailored Pants
Okay, feathers. I know it sounds like a lot. But a top with just a little feather trim at the cuffs or hem is so much fun and instantly festive.
Balance it with very simple tailored pants so the top can do its thing. I will not lie to you, I felt slightly ridiculous the first time I tried this, and then I got compliments all evening and became a believer.
Jewel-Tone Suit With Pointed Heels
Another suit, because I love a suit. A jewel-tone one, think sapphire or deep purple, feels bold and celebratory without a single sequin in sight. Pointed heels sharpen the whole thing up.
The nice part is that a colorful suit does all the talking for you. You barely need accessories, which suits me and my forgetful mornings just fine.
Black Cape Dress With Statement Earrings
A black cape dress is drama in the best way. The cape detail moves when you walk and makes even standing by the snack table feel a little theatrical.
Because the dress is doing so much already, I keep everything else simple and just add big statement earrings. This is a beautiful Christmas dinner outfit for a sit-down evening when you want to feel a bit elegant and don’t mind a touch of flair.
Metallic Skirt With Soft Knit
A metallic skirt is one of my favorite December surprises. Pair it with a soft, slouchy knit and the whole thing goes from “trying too hard” to “casually gorgeous” in an instant.
The mix of the cozy sweater with the shiny skirt is just so good. I keep a gold pleated one in my closet all year and only pull it out in December, which makes it feel like a treat.
Red Draped Dress With Kitten Heels
We started with red velvet and we’re ending with red too, because it’s the color of the season and I don’t apologize. A red draped dress is flattering on basically everyone, the way the fabric skims rather than clings.
Add kitten heels for a look that’s comfortable enough to wear all day and still very much dressed up. This is a lovely Christmas dinner outfit if you want something that looks fancy but lets you actually sit down and enjoy dessert. And enjoying dessert is, after all, the point.
