Olivia Culpo’s Guide to Holiday Dressing

Try Head-to-Toe Red
Photo: Gotham/GC Images

It’s the most wonderful time of the year—and dressing for it is half the fun. At least according to Olivia Culpo.

“I love to get all dressed up and throw parties around the holidays,” says Culpo, who was in N.Y.C. this week co-hosting her first big bash of the season with Stella Artois. “I grew up in a big Italian family, and we were always having people come over to celebrate. So now it just comes natural to me.”

Culpo’s favorite ways to celebrate this time of year include making her famous homemade biscotti, and of course, mixing and matching a bunch of chic and festive looks to carry her all the way through New Year’s Day.

Topping her wish list of late? Cozy sweater dresses, sleek over-the-knee boots, and, yes, lots of red. Read on for eight ways the street style star conquers every holiday party in style.

01 of 08

Start Shopping for Party Looks Now

Start Shopping for Party Looks Now
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Don’t wait until December to stock up on your cocktail attire, says Culpo. “There are so many good pieces at Zara, H&M, and Asos right now. And if you can splurge, I also love Monse for really beautiful night-out looks.”

02 of 08

If You’re the Host, Keep It Cozy

If You’re the Host, Keep It Cozy
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“When you’re having people over for the holidays, it's important to be comfortable,” says Culpo. “I like to do a sweater dress with an over-the-knee boot, a stocking, and a really chic hat. If you’re cooking, just go with a dark dress color, so you don't have to worry about getting it too dirty.”

03 of 08

When In Doubt, Overdress

When In Doubt, Overdress
Gotham/Getty

We all know dress codes can be tricky this time of year. Culpo’s take? Err on the dressy side. “I personally tend to be an overdresser rather than an underdresser in general,” she says. “But that’s mainly because I love clothes and I love putting together an interesting look. At a party, it can also feel strange when you’re too casual. If you’re really stuck, ask the host what they’re wearing and follow that lead.”

04 of 08

Try Head-to-Toe Red

Try Head-to-Toe Red
Gotham/GC Images

"I've been buying a ton of red lately," says Culpo. "And I love a monochromatic look during the holidays because it's so pulled together, yet still playful." If you're not sure about going full throttle, try a crimson pump. "I like suede or muted leather over patent, so you don't get the costumey Betty Boop effect," adds Culpo, citing Christian Louboutin as her favorite.

05 of 08

Layer Strategically

Layer Strategically
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There’s nothing worse than being cold when you’re all dressed up. Culpo’s trick is to cover up without adding bulk. “Layer a black turtleneck bodysuit under your jackets and dresses,” she says. “It also looks chic with a pair of trousers.”

06 of 08

Go For A Block Heel Over A Stiletto

Go For A Block Heel Over A Stiletto
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“Look for a great thick block heel shoe or bootie,” says Culpo. “Stuart Weitzman has really great ones that are comfy even when you’re on your feet all night long. If you’re more of a flats person, go for a Gucci loafer. That’s what I’ll wear when I have my girlfriends over for a little casual party.”

07 of 08

Have a Foolproof Outfit Ready to Go

Have a Foolproof Outfit Ready to Go
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In case of any last minute invites, Culpo says to have a chic look on standby, like a textured little black dress. Her other go-to? “A pair of high-waisted leather leggings,” she says. “You can put it with an oversize sweater or a sleek blazer, and it can take you somewhere casual or dressy.”

08 of 08

Kick Your Makeup Up A Notch

Kick Your Makeup Up A Notch
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The finishing touch? A red lip, of course. “I love MAC lip liner with a bold Laura Mercier lipstick on top,” says Culpo. Or try a cat eye. "I don’t wear any mascara when I do a cat eye, so all of the focus is on the liner."

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