Every December my sister calls me in a small panic because she has booked the family portraits again and nobody knows what to wear. It happens every single year, like clockwork, and every single year I tell her the same thing and then send her three photos anyway.
I love this time of year for the dressing up part. Honestly, the food and the twinkly lights are lovely too, but give me an excuse to pull out something velvet and I am a happy woman.
So I made this list, partly for her and partly for me, because my own list of festive outfit ideas had gotten completely out of hand.
20 Festive Looks to Wear All Season Long
Burgundy Velvet Dress With Bow Heels
There is nothing that says December quite like burgundy velvet. It photographs beautifully, it feels rich against a green tree, and it just looks like the holidays.
This is my go-to Christmas photoshoot outfit because it works whether you are standing by the fireplace or sitting on the floor with the kids.
Add a pair of heels with a little bow at the toe. Small detail, big charm.
Matching Tartan Skirts And Cream Sweaters
If you have ever wanted everyone in the group to look pulled together without being too matchy, this is the one. A matching family Christmas outfit built around tartan skirts and cream sweaters looks cohesive in photos but still lets each person be themselves.
My sister did a version of this two years ago and it is STILL her favorite portrait. The cream keeps it soft, the tartan keeps it festive, and nobody looks like a clone.
Red Satin Midi Dress With Pearl Earrings
Red satin. Say no more. A midi length keeps it elegant and easy to move in, which matters when you are chasing a toddler around the tree.
Pair it with pearl earrings and you have that classic, timeless look. This is the dress I would want in a holiday card photo outfit because red just pops against snow and greenery like nothing else. It reads Christmas from across the room.
Fair Isle Sweater With Velvet Trousers
Not every festive look has to be a dress, and I will not lie to you, some days I just want to be warm. A Fair Isle sweater tucked into velvet trousers gives you that cozy-but-put-together feeling.
The Fair Isle print does all the festive work for you. And the velvet trousers add just enough polish so you don’t look like you rolled off the couch (even if you did).
Black Lace Dress With Metallic Pumps
Black is always chic, always. A black lace dress feels a little more special than a plain one, and the lace catches light in the sweetest way.
Add metallic pumps to lift the whole thing. Gold or silver, your pick. This is a great caroling outfit if you want to look festive while standing outside in the cold singing off-key with the neighbors (which, in my case, I always do).
Emerald Velvet Suit With Silk Blouse
Okay this one makes me feel powerful. An emerald velvet suit is unexpected and so, so rich in color. Under the blazer, a simple silk blouse keeps it soft and feminine.
Green velvet against holiday decor is just gorgeous. My friend Dana wore this to her office party and got compliments all night. She is not a suit person normally, but this converted her.
Plaid Midi Skirt With Bow Cardigan
A plaid midi skirt is such a workhorse in December. It is festive without trying too hard, and it goes with almost everything in your closet already.
Top it with a cardigan that has a little bow detail, buttoned up or left open. It feels sweet and a bit nostalgic, like something you would have worn to a school concert as a kid.
Silver Sequin Skirt With Cashmere Sweater
Here is my favorite trick for December: pair something sparkly with something cozy. A silver sequin skirt on its own can feel like a lot, but tuck a soft cashmere sweater into it and suddenly it feels wearable.
This is the outfit I would grab for a holiday concert outfit, because you get to sit for a while and you want to be comfortable while still looking festive. The sequins do the sparkling, the sweater does the keeping-you-warm.
Red Wool Coat With Black Midi Dress
Sometimes the coat IS the outfit. A red wool coat over a simple black midi dress is one of those combinations that looks intentional even when you threw it together in five minutes.
The red coat photographs beautifully outdoors, especially with a little snow. And underneath, the black dress does the quiet work of pulling everything together. Easy and so classic.
Velvet Blazer With Satin Wide-Leg Trousers
I love a good trouser moment. A velvet blazer paired with satin wide-leg trousers feels dressy but relaxed, and it moves so nicely when you walk.
Of course you can dress it up with heels or keep it easy with flats.
Matching Burgundy Knits With Plaid Bottoms
Back to the matching idea, but cozier this time. Burgundy knits paired with plaid bottoms for the family is warm, festive, and forgiving of all body types and ages.
My husband will only agree to matching if it involves a sweater, so this is the compromise that keeps everyone happy in our house. And burgundy suits almost everyone. It is a very kind color.
Draped Jewel-Tone Gown With Velvet Clutch
If you have a fancier evening coming up, a draped jewel-tone gown is the move. Sapphire, emerald, ruby, whatever calls to you. The draping does all the flattering, so you don’t have to think too hard.
Carry a small velvet clutch to match the season. This would be a beautiful winter wedding guest outfit if you find yourself invited to one of those December celebrations, which somehow always seem to happen at the busiest time of year.
Tartan Dress With Sheer Black Tights
A tartan dress is such a December staple. It just IS Christmas, isn’t it? One piece and you are done, which I appreciate on a busy morning.
Add sheer black tights to keep your legs warm and to make the whole look feel a bit more grown up. Finish with some simple heels or ankle boots and you have an outfit that works for the party, the dinner, and the photos.
Cream Knit Dress With Red Accessories
Cream is underrated in December. Everyone reaches for red and green, but a soft cream knit dress feels so serene against all the busy holiday backgrounds.
Then you add the red in small doses. A red bag, red lip, red flats. It gives you that festive pop without going overboard, and it photographs like a dream. So gentle and pretty.
Satin Bow Blouse With Velvet Maxi Skirt
This one feels a little romantic. A satin blouse with a bow at the neck, tucked into a velvet maxi skirt, is elegant in a soft, old-fashioned way.
The bow is the star here. And the velvet maxi keeps the whole look feeling special and floor-sweeping. I would wear this to any evening event where I wanted to feel a bit dressed up but not stuffy.
Black Column Dress With Crystal Earrings
A black column dress is the definition of simple done right. Long, sleek, and easy, it lets your accessories do the talking.
So bring on the crystal earrings. Let them sparkle and catch the candlelight. This is the outfit for the person who does not want to think about their clothes all night but still wants to look like they made an effort. And honestly, that is most of us in December.
Red Cardigan With Metallic Pleated Skirt
Here is a combination that feels both cheerful and grown up. A red cardigan buttoned up over a metallic pleated skirt gives you that sweet holiday energy with a little shine.
The pleated skirt moves so beautifully, and metallic catches every bit of light around it. This is one I would wear to a nutcracker ballet outfit occasion, because the skirt feels a little bit like it belongs in the show itself. So festive.
Brooched Wool Coat With Velvet Mary Janes
There is something so elegant about a wool coat with a brooch pinned to the lapel. It feels like something my grandmother would have worn, and I mean that in the best way.
Pair it with velvet Mary Janes and you have a look that is polished from head to toe. The brooch is a small detail that makes people ask about it, and half the fun is telling the story of where you found it.
Midnight Blue Dress With Silver Heels
Not everything has to be red or green. A midnight blue dress feels festive in a quieter, more sophisticated way, and it is so flattering on nearly everyone.
Add silver heels to bring in that cool, wintry shimmer. This is a color that looks stunning under warm lights and next to a tree covered in white bulbs. So underused, and so lovely.
Chocolate Velvet Dress With Gold Accessories
And last but not least, chocolate brown velvet. It sounds unexpected, I know, but it is so warm and rich and it photographs like a hug. Trust me on this.
Finish it with gold accessories, warm gold, to bring out those cozy tones. A gold necklace, gold earrings, a small gold bag. This is the one I keep coming back to when I want to feel festive without wearing the same red dress as everyone else in the room.
