14 Cute Holiday Outfit Ideas That Are Stylist-Approved

Annual holiday gatherings with family and friends may sound merry and bright, but with so many parties to plan for, piecing together multiple holiday outfits can get exhausting, fast.

So, where can you turn to gather style inspiration?

If you're itching to get decked out in something that feels cozy but looks festive and cute, we've got you covered. Experts in the fashion space are sharing their ideas for holiday outfits, ahead, helping solve this dilemma before it even occurs.

You Can't Go Wrong With Something Red

Red is a classic choice for the holiday season, but Mickey Freeman has some ideas on how to sport the shade in a more contemporary fashion.

"Choosing classic options — like a red monochromatic knit top and pencil skirt, or a mid-length red dress with interesting textures or ornate embellishments — can really make all the difference in the world," the celebrity stylist tells InStyle. "Other outfit ideas that are all the rage this holiday season include a fierce red sequin suit, a retro, wine-red, velvet bodycon dress, and a casual red plaid shirt dress, which can be worn with or without a belt."

Break Out the Bra Top 

Even if it’s cold where you are, celebrity fashion stylist and Bare Necessities partner Kate Young encourages you to consider wearing a bra top for your holiday festivities. The underwear-as-outerwear trend is booming right now and is expected to be huge for winter 2023 — even in brisk conditions.

“I love a bra worn with a blazer and jeans for a casual, sexy outfit, or a bra under a suit to add an unexpected element to a look,” Young tells InStyle. Her personal favorite is the Bare by Bare Necessities Seamless Scoop Bralette, as it “gives a fitted, effortless look and is as comfortable as it is stylish with soft stretch ribbed fabric and a scoop neckline in the front and back.”

Feel Fancy in Faux Fur

When it comes to holiday outfits, Tobi head stylist Joanna Angeles says she associates the time of year with faux fur. For an ensemble that looks and feels luxurious, she says to "take a knee-length coat with faux fur trim and layer it with a fitted, long-sleeved turtleneck, leather mini skirt or shorts, sheer tights, and knee high heeled boots. Metallic accessories, such as a clutch or headband, will add that much-needed pop of sparkle."

Shine Bright in Sequins

"Nothing says festive like sequins," celebrity stylist, Tiffany Briseno tells us over email. "However, instead of going for the party dress, try a matte sequin suit paired with a 1970s platform sandal for a fun and elegant look. To take your look to an unexpected level, try this in a neutral hue like brown or camel."

Dainty Jewelry Can Still Make a Statement

Celebrity stylist and Pandora Jewelry partner Erin Walsh says she’s a big believer in being “‘incidentally fabulous’- looking amazing and sparkly and interesting and powerful all the while seeming like it’s totally effortless.” To achieve this, Wash piles on fine, sparkling accents, like layered pendant necklaces and a variety of dainty earrings stacked up the ear (much like these Diamonds by Pandora stud earrings).

“[The goal is to have your jewelry] come across more like ‘dusting,’” Walsh tells us. “I think the key is to find a collection you love that mixes in with both everyday holiday and evening holiday, and then you really can step into your power. Whether that’s at a party, a meeting, dinner, or even at home.”

Wear Wide-Leg Trousers

Wide-leg trousers are an illusion. To the naked eye, they look formal. To the wearer, they're a much more comfortable alternative to something like skinny jeans. Not to mention they're usually roomier around the waist — a definite perk when you're celebrating food-focused holidays.

"You want to look just as polished from the moment you arrived to post pumpkin pie, [and] the high-waisted wide-leg trouser is not only flattering for all body types, but it is also both comfortable and perfect for a dinner party," notes Briseno. "Try this with a romantic sleeve top and some statement earrings in your favorite holiday jewel tones."

Swap Dress Pants For Cargo Styles

Cargo pants are everywhere at the moment and the trend is set to stick around through 2023. So it's no wonder that national style expert and fashion stylist Naina Singla points to the refined cargo pant as one of her favorite — albeit unexpected — items to wear for the holidays.

“Most people associate cargo pants as strictly casual pants. But, did you know you can elevate them by simply choosing them in a different fabric?" she asks InStyle. "Some of the easiest ways to dress up a cargo pant is to find them in satin or leather. You can pair them with a simple cashmere sweater for a chic yet comfortable look. Or, you could add a sequin cami or blazer for a more dressed-up and festive holiday look. Try it, you might just surprise yourself."

Add Leather For Texture

While you could reach for sequins and pearls, celebrity stylist Sonia Young says she's leaning toward all things faux leather for a pop of texture this holiday season.

"There are so many amazing leather pants — faux leather, patent leather — that can easily be worn from day to night, making it a perfect holiday wardrobe staple," says Young. She's especially drawn to a pair of Commando Patent Leather leggings, as "they can go to the office with an oversized sweater and loafer, and to a dinner date in a blazer and heels."

Embrace the Loungewear Look

If you want to go the comfy route this holiday season, there are ways to elevate your loungewear, including adding a heel to your favorite PJs.

"What's better than having a glass of wine in the comfort of your pajamas?" Young asks. The answer: nothing. As for which way to lean when picking out your set, the stylist has some recommendations. "I am a huge fan of Olivia Von Halle, Sleeper, and Morgan Lane."

Red, white, and green are obvious choices for your holiday color palette, but because we're coming out in a big way this season, JLUX co-founder, Teresa Jaide says every detail matters.

"Year after year, we love reaching for our rich emerald green or ruby red velvets," she tells InStyle, before adding her pick for switching things up a bit. "This year, in addition, we are going for our new favorite hue for intensity and elegance: midnight blue!"

Say Yes to Slip Dresses

According to Rebecca Clarke, head of design at Nasty Gal, the slip dress is a wardrobe staple. For the holidays, she tells InStyle that she's especially loving slip dresses with a ruched side detail as a nod to the late 90s/Y2K moment. "Streetwear detail meets glamour for the holidays."

Suit Up

Three-piece suits have been on the rise since 2021, so it’s no surprise why Singla would suggest a set as a holiday outfit option. But the stylist isn’t recommended dark and dreary colors to mirror the winter weather; instead, she’s leaning towards white or ivory for the season’s upcoming festivities. 

“Although a women's suit can typically offer a more understated classic look, a lightweight wool suit set with a blazer, vest, and trousers comes together as intentionally polished and elegant. You can never go wrong with a suit for any holiday event."

Make It Metallic

In an exclusive interview with InStyle, style expert, and Amazon Live style host Katie Sands revealed she loves a metallic moment for the holidays, and this year is no exception.

"I've been seeing a lot of metallic suit sets, and I love that they give that power suit feel while also being very holiday-oriented," says Sands. "Style with any nude or black boot in your closet or maybe a little kitten heel, a bralette and you're ready to rock!"

Go Sleek and Simple With a Blazer Dress

As far as celebrity stylist and fashion consultant Amanda Sanders is concerned, blazer dresses are a great go-to if you'll be transitioning from the office to a holiday party.

"I'd pair it with suede over-the-knee boots, silver drop earrings, and a statement ring, and finish off the look with a moto jacket and suede bucket bag with silver hardware," she says. "All pieces are great winter staples for seasons to come!"

Opt for Emerald

If red items aren’t plentiful in your wardrobe, or you’re just not a fan of the color, personal stylist, Allie McKenna recommends opting for another holiday season staple shade: Emerald.

“Red is always appropriate, but kind of obvious,” she tells InStyle. “A deep emerald “Juliet” top is perfect for a swanky holiday party, paired with a black skirt and over-the-knee boots.”