What to wear for every kind of holiday party, according to an expert

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The holidays will be here before we know it — and that means presents, plenty of delicious food and, of course, parties galore. And whether you’ve got company cocktails, family dinners or more formal bashes filling up your calendar, you’re going to need some fun and festive looks to fit the occasion.

Enter Bloomingdale’s personal shopper Stacey Oliver, who recently helped Page Six anchor Astra and I put together some party-ready looks to help us take on the most celebratory season in style.

Read on to see which styles Oliver selected — and to shop them all for yourself.

Snow angel

Astra wearing a white minidress Page Six Style

“I love a winter white moment,” Oliver says of this “fun, festive” SIMKHAI minidress, adding that the holidays are the perfect “excuse to wear some bling.” (The silver SIMKHAI shell clutch and “Cinderella-inspired” Steve Madden slingbacks are equally eye-catching.)

Shop the look:

SIMKHAI Ziva Embellished Minidress

Simkhai Ziva Embellished Minidress Bloomingdale's

SIMKHAI Monet Shell Clutch

Simkhai Monet Shell Clutch Bloomingdale's

Steve Madden Fete Embellished Slingback Pumps

Steve Madden Fete Embellished Slingback Pumps Bloomingdale's

Gold rush

Elana wearing a gold gown and black blazer Page Six Style

“This is great for a more dressed-up or more formal holiday party,” Oliver says of this “gorgeous” gold Jason Wu Collection gown she styled with a “chic” ba&sh blazer and sleek SIMKHAI clutch.

Shop the look:

Jason Wu Collection Satin Gown

Jason Wu Collection Satin Gown Bloomingdale's

ba&sh Shawn Notch Collar Double Breasted Blazer

Ba&sh Shawn Notch Collar Double Breasted Blazer Bloomingdale's

SIMKHAI Rolo Clutch

Simkhai Rolo Clutch Bloomingdale's

Wrapped in red

Astra wearing a red sweater dress Page Six Style

“Red is such a festive color — it’s such a fun pop,” Oliver says of this layered Maje minidress she paired with matching Stuart Weitzman pumps for Astra, which would work just as well for the office as for a holiday fête.

“You can wear the sweater with a pair of jeans on the weekend. I love a piece that’s versatile and can get you beyond just the party.”

Shop the look:

Maje Roquette Layered Knit Minidress

Maje Roquette Layered Knit Minidress Bloomingdale's

Stuart Weitzman Stuart Power 75 Pumps

Stuart Weitzman Stuart Power 75 Pumps Bloomingdale's

Seeing stars

Elana wearing a starry sweater and printed maxi skirt Page Six Style

“This is a great look to wear to the office, and then to the party afterward,” Oliver says of this starry Altuzarra sweater and printed maxi skirt. “These are pieces that you can mix and match and wear over and over again; it’s not just a one-and-done party look.”

Shop the look:

Altuzarra Jared Mock Neck Sweater

Altuzarra Jared Mock Neck Sweater Bloomingdale's

Altuzarra Tullius Printed Maxi Skirt

Altuzarra Tullius Printed Maxi Skirt Bloomingdale's

Malone Souliers Valeria Pointed Toe Slingback Pumps

Malone Souliers Valeria Pointed Toe Slingback Pumps Bloomingdale's

Prints charming

Astra wearing a floral-print turtleneck dress Page Six Style

With its long sleeves, high neck and modest hemline, this asymmetrical Etro dress would be a great choice for a holiday gathering with family or in-laws — and the floral print keeps the look fresh.

Shop the look:

Etro Asymmetric Hem Dress

Etro Asymmetric Hem Dress Bloomingdale's

Steve Madden Raz Pumps

Steve Madden Raz Pumps Bloomingdale's

Groovy, baby

Elana wearing a floral-print maxi dress and furry vest Page Six Style

“This outfit speaks for itself,” Oliver says of this maximalist layered look from La DoubleJ, which you can contact her directly to purchase. “It’s so fashion forward. Something different, but still really festive and fun.”


Why Trust Page Six Style Shopping

This article was written by Elana Fishman, founding editor of Page Six Style. Elana applies her celebrity fashion and beauty expertise to shoppable content for fellow fans as the host of video series including Style TrialHeart to Cart and Beauty Scoop — and by tracking down every Taylor Swift-worn style so you can shop it, too. Elana consults celebrity stylists on the latest street style and red carpet trends, researches which celebrity-backed brands and products are worth it, and chats with the stars themselves for beauty and fashion recommendations. Prior to Page Six Style’s inception in 2018, Elana covered celebrity fashion at Vox Media, Lucky, Marie Claire and Teen Vogue.


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