15 Cute Holiday Outfits You Won't Regret

Picking out the perfect outfit for your holiday shindig can be stressful. Whether you're celebrating with a family dinner or a big party, there are so many factors to keep in mind when choosing Christmas Day outfits, Hanukkah ensembles, and all manner of party attire. You want to be festive but not kitschy, and cool but still family-time appropriate. To help you find an outfit you won't end up regretting, we've rounded up some easy ways to take potentially problematic outfits and make sure they're perfect for your festivities. We have some tips on how to style a cheery sweater, a sparkly dress, festive colors, and more. Scroll down to see the fail-proof ways to wear classic holiday outfits you won't regret.

The Over-the-Top Midi Dress

Holiday outfits with over-the-knee boots


Style du Monde

Everyone loves an over-the-top, festive dress for the holidays. Pair it with high leather boots to make sure you're not too dressy for the occasion.

The Holiday Sweater

Holiday sweater outfits


Sandra Semburg

The classic holiday sweater doesn't have to look frumpy. If you want to nail one this year, pair it with an A-line skirt and pumps to look merry yet sophisticated.

The "Skin-Baring" Look

Holiday dress outfits


Style du Monde

Have the perfect dress that's just a little too revealing for hanging with your relatives? Throw a long-sleeve top under it for a cool, edgy look that's family-appropriate.

The Sparkle

Sequin holiday dress outfits


Sandra Semburg

Sparkle is a no-brainer when it comes to holiday dressing. Avoid over-the-top shine by choosing a muted metallic dress with a sophisticated shape.

The Most Ubiquitous Colors

Holiday outfits with blazers


Sandra Semburg

Nothing screams holiday spirit like throwing some red and green into your outfit. To avoid looking tacky, subtly work the shades into your look via accessories and accents.

The Layered Turtleneck

Holiday outfits with turtlenecks



Any dress is made better when layered over a turtleneck. We suggest a white turtleneck with a darker-hued dress to provide some chic contrast. Pair with black or bold-colored booties.

Neutral Hues

Neutral Holiday outfits



This holiday season, forget your blacks and blues; instead, pull out a much-loved sartorial color scheme: neutrals. From cream-colored sweaters to tan pants, you'll look elegant and sophisticated.

The Pop of Print

If you're hoping to keep it classic but still want to show a bit of personality, try adding a pop of print with your pumps. From leopard to snake, animal prints are continue to dominate.

The Tucked Trouser

Chic holiday outfits



A sleek pair of trousers will get you through many a holiday event, but tucking them into knee-high boots—this season's favorite shoe style—makes for a particularly stylish look.

The Suit Set

It's suiting season, and there's no better or simpler outfit to wear to your next holiday shindig. A matching suit set makes for an immediately put-together look. Add a bag in a similar hue and you're set (yes, pun intended).

The Blazer Dress

Christmas Day outfits with tights



Any dress can be made winter-appropriate with a pair of black tights. This includes a blazer dress, winter's answer to summer's flowing cotton dresses. Belt your blazer and get to the party!

The Simple Skirt



Every fashion girl's closet is likely overflowing with pleated skirts—a fall fashion staple. Simply pair one with an oversize sweater for a look that will keep you cozy all night long.

The Cool Culottes

Culottes are making a comeback, and we're here for it. Grab a leather pair and style them with knee-high boots and a turtleneck for our favorite holiday look. 

The Holiday Jumpsuit

Holiday jumpsuits



There's no outfit more easily effective than a stylish jumpsuit. Whether your is denim or velvet, this is an outfit you can easily repeat for numerous holiday events. 

The Winter White

Don't shy away from winter whites for the ultimate holiday look. The snow outside will practically be a matching accessory. 

Looking for more holiday outfit inspo? Try these holiday tops you can wear with everything.

This post was originally published at an earlier date and has since been updated.