38 Chic Holiday Party Outfits—Created With Only TEN Key Wardrobe Pieces

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Playing Gretta Monahan & Zanna Roberts Rassi Create 38 Holiday Party Outfits With 10 Key Wardrobe Pieces
Gretta Monahan & Zanna Roberts Rassi Create 38 Holiday Party Outfits With 10 Key Wardrobe Pieces Aired November 27, 2018

When it comes to fashion, you can actually do more than you think with less—all you need is a little creativity.

We called on fashion experts Zanna Roberts Rassi (Fashion Editor-at-large of Marie Claire) and Gretta Monahan (founder of Gretta Luxe and author of “Style and the Successful Girl”) to help two viewers plan their holiday party looks, using some basics you probably already have in your closet plus a few trendy items!

The gal pals — Natasha from Long Valley, New Jersey, and Pam from Manalapan, New Jersey — are both headed to several parties together and want to make sure their outfits are as different as their personalities.

Here are the 10 pieces you need to mix-and-match all 38 party outfits the style pros put together.

THE BASICS

Black Turtleneck
Rachael Ray Show

1) FITTED BLACK TURTLENECK

According to Zanna, a turtleneck should be a key piece in everyone’s closet. It’s great on its own, but also useful for layering underneath dresses, blouses, jackets and more. (Not to mention, it’s perfect for those chilly winter days!) Channel Audrey Hepburn’s classic look with a fitted black turtleneck, black skinny jeans and update with a colorful heel.

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Knee-High Boots
Rachael Ray Show

2) BLACK CHUNKY HEEL KNEE-HIGH BOOTS

Winter calls for stylish knee-high boots that can be paired with just about any outfit. Zanna switched up the look by putting the boots with pants, dresses, skirts and a jumper. The boots have just enough of a heel to give Pam some height, but are still comfortable enough for all-day wear. If you’re on the hunt for the perfect pair of chunky knee-high boots, you’ll want to follow these tips from Zanna.

Denim Shirt
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3) LONG-SLEEVE DENIM BUTTON-UP

The beauty of a long-sleeve denim button-up is that it can be dressed up or down depending on the occasion. For Natasha, Gretta paired the denim piece with a dress, jeans, a jacket and more, and switched up her shoes to pull the look together. Gretta says, “In our closets, we put dressy with dressy and jeans with jeans. Mix it all up for the holidays. It’s a great way to build a look.”

Black Blazer
Rachael Ray Show

4) TAILORED BLACK BLAZER

This should be a staple in you closet. Dress up a basic black blazer with a skirt and heels or go casual with a denim top and a pair of jeans. Gretta picked out this cute option that is tailored to the body and hits just below the waist to show off Natasha’s shape. It’s the perfect way to tie just about any outfit together.

Knit Sweater
Rachael Ray Show

5) PATTERNED KNIT SWEATER

No winter wardrobe is complete without a comfy knit sweater. Gretta suggests being bold and mixing the piece with different materials. Go casual by pairing the sweater with jeans or wide-legged pants and tennis shoes. Or, match it up with dressier pieces, like a sequin skirt or cocktail dress.

TRENDY HOLIDAY PIECES

Leopard Print
Rachael Ray Show

6) LEOPARD PRINT COAT OR SKIRT

“Leopard is the print of the season, without a doubt,” Zanna says. She and Pam mixed and matched this leopard coat and skirt as the standout pieces in several outfits. (We love the idea of turning the coat into a dress with those super cute knee-high boots!) Additionally, the coat and skirt can be combined and the look comes together with the help of a basic black turtleneck.

Red Jumpsuit
Rachael Ray Show

7) FLOWY RED JUMPSUIT

A jumpsuit is the fashion piece that keeps on giving.

As Gretta puts it, “I love a jumpsuit. When you do a jumpsuit — whether you want to have more coverage and put tops and button downs over it — you can cover up when it’s cold. But it can also be really dressy, cool and comfortable. And it’s all done in one piece!” Pam was dressed in a flowy, red jumpsuit that was cinched in the waist with a bow. The piece can also appear to be a pair of pants by throwing your favorite sweater or shirt on top.

Sequined Skirt
Rachael Ray Show

8) A MIDI-LENGTH SEQUINED SKIRT

Gretta and Natasha had fun with this eye-catching sequined skirt. The piece could be worn normally with a knit sweater or blazer to give the outfit a little extra ‘oomph.’ But because of the longer length, the skirt can also be pulled up to give the illusion of a dress. Cocktail party approved.

Slip Dress
Rachael Ray Show

9) SILKY RED SLIP DRESS

This silk slip dress can easily transition from day to night. Layer it on top of a black turtleneck with a pair of knee-high boots for a more conservative, everyday look. For New Year’s Eve or a night on the town, lose the shirt underneath and swap the boots for a colored heel. It’s effortlessly chic.

Sparkly Heels
Rachael Ray Show

10) SPARKLY HEELS

‘Tis the season for sparkly heels! Pairing these pointed toe heels with a formal dress or skirt is a no-brainer. But Gretta adds a bit of glam to Natasha’s everyday style by adding the heel to more casual looks. A simple black jumpsuit or an otherwise laid-back denim outfit get an upgrade from these blinged-out stilettos.

Together, Team Zanna/Pam and Team Gretta/Natasha were able to put these 38 looks together with the help of J. Crew. Both guests went home with a $1,000 gift card from the retailer, just in time for a little holiday shopping.

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