The holiday season is the perfect time to shine, and with the right outfit, you can capture that festive magic while ensuring your wardrobe works hard for you year-round. Choosing versatile pieces that blend elegance with practicality allows you to enjoy your looks well beyond the holiday festivities. Here’s my guide to stylish, dressy holiday looks and three styling tips to extend their life past the New Year.

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Dressy Holiday Outfit Inspiration

Instead of a classic LBD, opt for a long metallic skirt instead!
The little black dress (LBD) is always a holiday staple, but this season, try a metallic long skirt instead and pair it with a cozy cream cashmere sweater or a simple black top and black suede holiday pumps! Add some understated but festive jewerly like a gold hoop earring and a bracelet stack for a party, and then you can easily pair the sweater/top and jewlery with denim and sneakers for a more casual look.

(Outfit Details: Skirt, Pumps (old) – similar here and here, Bag (old) – similar here and here)

Shimmering Separates
Shimmer blouses make a bold holiday statement. Mix and match these with neutral pieces in your closet, like denim or tailored pants, to effortlessly transition them into non-holiday outfits.

Faux Fur Jackets
Faux fur jackets are festive but versatile. I LOVE a cropped faux fur jacket as they look great with dressy pieces and denim! They radiate warmth during the holidays and seamlessly fit into formal events or date nights all year long.

3 Tips to Pick Holiday Pieces That Last

(Outfit Details: Skirt, Pumps (old) – similar here and here, Top, Bag (old) – similar here and here)

Tip 1 – Focus on High-Quality Fabrics
Invest in well-made pieces with luxe fabrics like silk, velvet, or satin. These materials not only look festive but also wear beautifully beyond the season. A velvet blazer, for instance, can be your standout holiday piece but will pair effortlessly with jeans and a simple tee for a chic winter look.

Tip 2 – Choose Timeless Cuts and Styles
Skip overly trendy silhouettes and go for classic shapes that endure. A tailored wrap dress or a sleek jumpsuit will always feel fresh, no matter the season. When accessorizing for the holidays, let jewelry or statement shoes bring the festive flair.

Tip 3 – Opt for Dual-Purpose Accessories
Accessories can make or break an outfit. For the holidays, choose pieces like metallic clutch bags or glittering earrings that feel festive but can easily complement a wedding outfit, dinner date look, or even work attire later on.

(Outfit Details: Skirt, Top, Watch – similar here)

By selecting versatile, high-quality pieces in timeless cuts and colors, you can create dressy holiday looks that are as practical as they are stunning!

Which of these tips will you try this holiday season? Let me know in the comments!

-Natalie, xo

Photo Credit: Willow & Wren Photography

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