Every December I have the same little panic. The invites start rolling in, the calendar fills up, and I stand in front of my closet at 5 pm the night of a party wondering why I own so many things and yet nothing to wear.
My sister and I text each other outfit photos all month long. She lives two states away and we can’t do the dressing rooms together anymore, so this is how we do it now. She sends me a mirror photo, I tell her yes or no, and honestly it works.
So this year I decided to get ahead of the chaos and actually think about it before the day of. I made a list.
20 Looks to Get You Dressed and Out the Door This December
Paprika Blouse With Satin Trousers
There is a warm reddish-orange shade that just looks like the holidays without screaming it, and paprika is that color. A blouse in this tone paired with satin trousers is the kind of look that photographs beautifully in candlelight.
The satin catches the light when you move, which does half the work for you. I wore something like this to my mom’s a couple years ago and got compliments all night, and I did almost nothing.
Black Slip Dress With Kitten Heels
If I could only own one thing for December it might be a good slip dress. An all black dinner outfit is the answer to about 90% of “I have nothing to wear” nights, and this is the easiest version of it.
Kitten heels keep it walkable, which matters when the parking situation is what it always is in December. Add a little pendant necklace and you’re done.
Dark Jeans With Draped Top
Not every dinner calls for a dress and I will not pretend otherwise. Dark, clean jeans with a soft draped top is a cute dinner outfit casual enough for a low-key evening but still put together enough that you look like you tried.
The draped top is the trick here. It adds a little softness and movement so the jeans don’t read as too plain. So easy.
Butter Yellow Dress With Flats
Okay, hear me out on this one, because a yellow dress in December sounds strange. But that soft, buttery yellow that was everywhere this year is gorgeous against winter’s grey light. It’s unexpected in the best way.
Pair it with simple flats and you have a look that feels fresh and a little bit spring-in-winter. My friend Dana wore a version to a family dinner and everyone kept saying how happy the color made the table feel.
Suede Jacket With Silk Skirt
This is one of those high-low combinations that just works. A slightly rugged suede jacket over a fluid silk skirt gives you texture, and texture is what makes an outfit look expensive when it isn’t.
The jacket keeps you warm during the walk in from the car, which is a genuine concern where I live. And then you can leave it on all night because it looks like it belongs.
White Tank With Balloon Pants
A plain white tank sounds too simple to make a list like this. But balloon pants change everything. The volume on the bottom balanced against something fitted on top is such a flattering, modern shape.
Add gold hoops and a heeled sandal.
Burgundy Knit With Pencil Skirt
Burgundy is the color of the season and I am not mad about it. A fine burgundy knit tucked into a pencil skirt is such a classic silhouette. It’s the sort of thing my grandmother would have approved of, and she had opinions.
The knit keeps it cozy so you’re not freezing, and the pencil skirt keeps it polished. This is a great one for a dinner where you’re not totally sure how dressy everyone else will be.
Lace Blouse With Tailored Trousers
Lace can go wrong very fast, so the way to keep it grown-up is to pair it with something structured. A lace blouse with sharp tailored trousers balances the pretty with the crisp, and the result is lovely.
I like this for a work-adjacent dinner, the kind where you want to look nice but not like you’re going to a dance. In fact, it’s one of my favorites on this whole list.
Leopard Skirt With Black Top
Leopard print reads as a neutral to me now, which I know is a little silly, but there we are. A leopard midi skirt with a simple black top is a look that feels fun without a lot of effort.
The skirt does all the talking so you keep everything else quiet. Black top, dark boots, small earrings. Done and out the door.
Strapless Dress With Pointed Flats
A strapless dress feels like a lot until you dress it down with pointed flats instead of heels. Then it becomes surprisingly wearable and comfortable, which is what we all actually want at a long dinner.
Throw a soft cardigan or a little jacket over your shoulders for the cold parts of the evening. And you can take it off once you’re seated by the warm part of the room.
Chocolate Blazer With Dark Denim
Brown is quietly having a moment and a rich chocolate blazer is proof. Over dark denim, it’s the kind of relaxed-but-sharp combination that works for basically any December plan.
I wore this to a casual get-together last week and felt like the most put-together version of comfortable, if that makes sense. The blazer really is the hero. Buy the brown blazer, is what I’m saying.
Satin Cami With Wide-Leg Pants
A satin cami is one of those pieces I underestimated for years. Under a blazer or on its own, tucked into wide-leg pants, it looks so much fancier than the effort it takes.
The wide-leg pants keep it from feeling too dressy, so it’s this nice in-between. You could wear this to a fancy dinner or a not-so-fancy one and be right either way.
Red Midi Dress With Slingbacks
Red at Christmas is a little expected, I know, but sometimes expected is exactly right. A red midi dress in a deep, true shade is a proper statement, and this is where I’d argue you can go full holiday. A christmas dinner outfit classy enough for the fanciest table on your calendar, and this red dress is it.
Slingback heels keep it elegant and, more importantly, they slip off under the table when your feet have had enough. And they will.
Sheer Blouse With Column Skirt
A sheer blouse with a little something underneath, over a long column skirt, gives you this elongated, elegant line that is very flattering. The column skirt does something magic for the silhouette.
Keep the colors in the same family, like a soft grey blouse over a charcoal skirt, and it reads as intentional and calm. This one photographs beautifully, if that’s something you think about.
Funnel Jacket With Mini Dress
A cozy funnel-neck jacket over a little mini dress is a fun way to do dressy in cold weather. The jacket keeps the top half warm and casual, and the mini keeps the whole thing feeling festive.
Add tights and boots so your legs aren’t freezing on the walk in. This is a younger, playful look and I’m here for it.
White Shirt With Slip Skirt
The crisp white button-down keeps showing up in my life and I keep letting it. Tucked into a satin slip skirt, it’s that perfect mix of casual and dressy that I reach for again and again.
Roll the sleeves, undo a button or two, add a delicate chain. It’s such an easy trick and it never looks like you’re trying too hard, which is the point of the trick.
Fringed Top With Straight Leg Jeans
A little fringe brings movement and fun to an outfit, and December dinners can use a bit of fun. A fringed top with straight-leg jeans is festive without any effort at all.
Every time you move the fringe moves too, which catches the light in a nice way. Keep the jeans simple so the top gets to be the star.
Black Tuxedo With Satin Camisole
If you want to feel like the most put-together person in the room, a black tuxedo suit with a satin camisole underneath is the answer. It’s sharp, it’s timeless, and it makes you stand up a little straighter.
I love this for a birthday dinner outfit winter plans included, because it works whether you’re the one being celebrated or just showing up looking good. It’s honestly one of the most useful looks here.
Poplin Dress With Statement Earrings
A structured poplin dress has such a clean, architectural feel to it. On its own it can look a touch plain, which is exactly why you add big statement earrings.
The earrings do all the decorating so the dress stays simple. It’s an easy formula: quiet dress, loud earrings, good night out.
Oatmeal Cardigan With Straight Jeans
And we end on the coziest note, because not every dinner is a dress-up affair and I refuse to pretend otherwise. An oatmeal-colored cardigan over straight jeans is warm, soft, and just enough.
Add a nice pair of boots and a little lipstick and you look intentional rather than like you gave up. This is my “I love these people but I’m tired” outfit, and December has a lot of those nights.
