The best holiday dresses depend on where you’re going. For a work party, pick a midi in a matte fabric like crepe or velvet. For a family dinner, choose something with stretch and sleeves, like a knit. For New Year’s Eve, go for satin or sequins and save the shine for midnight.
December fills up fast. A work party one week, a family dinner the next, then New Year’s Eve and a few smaller invitations squeezed in between. Buying a new outfit for each one isn’t realistic, so the useful question is which dress suits which night, and which ones can cover more than one.
Holiday dresses for the work party
A work party sits in an awkward spot. You want to look like you made an effort without looking like you’re heading somewhere else afterward. A midi dress does most of that for you. The hem lands below the knee, so you can sit, stand and balance a plate without thinking about it.
Fabric matters more than color here. Crepe, ponte and velvet hold their shape through hours of standing around, and they don’t catch the overhead lights the way shiny satin can. Dark green, burgundy and navy look festive without feeling like a costume, and a black dress never goes wrong. If you already own one, our guide to black dress styles that flatter every figure will help you pick the cut that works for you. Earrings and a good belt are enough to turn it into a party dress.
Sleeves are worth a thought. Offices run cold, and a dress with three-quarter or long sleeves saves you from a blazer you didn’t want to wear. For shoes, a low block heel or a kitten heel lets you stay in them for the whole evening, which matters more than anything else on your feet by the third hour.
Holiday dresses for the family dinner
Family dinners are about sitting. You’ll be at the table for a long time, usually after a big meal, so the dress has to give a little. Knit and jersey are the easy answer. A knit midi with a turtleneck or soft cowl neck looks put together and doesn’t dig in at the waist. If you want ideas for styling one, we’ve covered sweater dresses in detail.
Color can be warmer and softer here. Rust, forest green, cream and camel look good in candlelight and photograph well when someone gets the phone out for the group picture. Skip anything strapless or very fitted through the hips, since you’ll spend most of the night sitting down, hugging relatives and reaching for dishes.
Pockets are a small thing that makes a big difference. A dress with them lets you keep your phone and lip balm on you without carrying a bag around the house.
Holiday dresses for New Year’s Eve
New Year’s Eve is the one night where shine makes sense. Sequins, metallic knits, satin and beaded fabrics all work, and it’s the right occasion for a shorter hem or a bare back if that’s your style. A satin slip dress is the easiest option. It looks good on its own and layers well under a blazer or cropped jacket for the walk to the car.
Pick one statement and keep the rest plain. A sequin dress wants simple shoes and small jewelry. A plain satin dress can handle bold earrings. Wearing both at once tends to look like too much by ten o’clock.
Think about the practical side too. Sequins can scratch under the arms, and long beaded hems catch on things. Sit down in the dress at home before you commit to it. If you can’t lift your arms to hug someone at midnight, choose another one.
Holiday dresses for smaller gatherings
Not every event needs a full dress-up. School concerts, tree-trimming afternoons and drinks at a friend’s place call for something in between. A printed midi, a wrap dress or a plain shirt dress with tights and boots works well for all of them.
Red and green are fine in small doses, like a green dress under a cream coat, but you don’t have to commit to the theme. A dress in a deep color that you’d wear again in January is a better buy than one covered in sparkle that works for a single evening. That’s also the easiest way to make holiday dresses earn their place in your closet, since the plain ones keep getting worn after the decorations come down.
Staying warm in a dress
December dresses have a problem summer one doesn’t, which is the weather. Tights in black or a slightly sheer weight take care of bare legs, and knee-high boots under a midi hem keep you warm without hiding the dress. For the layers on top, our winter layering guide shows how to add a cardigan or coat without flattening the shape of a dress.
If the evening involves a walk outside, a long wool coat or a faux fur piece, like the ones in our coat and fur guide, finishes the look and keeps the cold off. Choose a coat that’s the same length as the dress or longer, so no hem sticks out underneath.
Checking a dress before you buy it
First, do some tests before paying for the dress. Are you able to sit down in comfort? Can you raise your hands above your head? Are you able to walk up the stairs without holding onto the skirt? If your answer to all these questions is no, the dress is going to annoy you within two hours, no matter how nice it looks hanging in the store.
Second, consider how many times would you wear the dress. A dress that changes its character depending on the pair of shoes and a jacket is cheaper per use than the one that suits only for one party. For example, the black velvet midi can be used for both the office party dressed in tights and loafers and a dinner in heels and gold earrings. The rust knit can be worn both at Thanksgiving and on a cold day of February.
And finally, shop your own closet first. With a dress that you already have, but styled with a new belt or more daring earrings, you get a brand new outfit.
