Holiday Outfits

November 20, 2025

Wit & Whimsy wearing a holiday outfit

This holiday season I am feeling particularly lucky to have holiday occasions on my calendar that span two of my favorite cities. I will be getting doses of the holiday season in London and New York and I am so excited to get dressed up in festive holiday outfits for a variety of special meals, parties, and outings.

If you’re looking for some inspiration as you get dressed for your holiday parties and outings, this post has you covered. Get ready for sequins and sparkle, tulle and fringe and also many a metallic moment…

Holiday Outfits

So, whether you’re getting dressed for holiday parties, work soirees, New Year’s Eve, Christmas, Hanukkah or friend gatherings, you can shop my Holiday Outfit Edit to have you prepped and ready to celebrate this season. All different retailers, all different price points.

And also don’t miss this year’s Budget Friendly Holiday Outfits Guide!

Below are a bunch of my holiday looks from years past to get you inspired as you shop. I also just picked up this Tanya Taylor number that is going to be so much fun to wear to a party (size 8) and this darling Hill House dress in the beautiful metallic brocade (size L).

Tuckernuck Velvet Holiday Dress

Tuckernuck Velvet Mini dress (size L) and Ann Mashburn velvet mules.

La Ligne Sequin Dress

La Ligne Sequin Dress from 2024. La Ligne makes such beautiful dresses.

Tuckernuck Holiday Outfit

Sequins! Bows! I am never more a maximalist than this time of year. Shop my dress HERE (wearing a L but likely could have done a M!) Paired it with my favorite Sarah Flint Pumps (use code SF-MEGHAND15 for 15% off at Sarah Flint!)

Wit & Whimsy wearing a faux fur jacket

I love a faux fur jacket as a festive topper this time of year! Would be particularly cute with a pair of sequin pants.

Holiday Outfit Ideas: Alice and Olivia dress and Stuart Weitzman heels

This dress is by Alice and Olivia who makes such fun party frocks (I got this one two years ago). Seen styled with Stuart Weitzman heels.

Vince Dress from 2023 and Stuart Weitzman heels.

Vince Dress from 2023 and Stuart Weitzman heels.

Holiday Outfits: menswear inspired with a tuxedo bar jacket

Go menswear inspired with a tuxedo bar jacket.

Holiday Outfits: a sequin skirt from J.Crew

I adore a sequin skirt at this time of year! This one and the one below are from J.Crew from seasons past. The coat and boots remain available to shop.

A velvet dress styled with a belt and riding boots

A velvet dress is always fun. Wearing this one above (size L) with an added belt. Then styled with riding boots as I was in the French Alps!

London at Christmas Time I party Holiday Outfit

Go monochrome when you’re not sure what to wear. Also, be sure at least one piece has a festive element like sparkle or feathers. Seen wearing my Sarah Flint Pumps here.

plaid pieces from J.Crew Factory

Historically I’ve found very fun plaid pieces at J.Crew Factory.

Holiday Outfit Plaid Skirt

Nap Dress paired with favorite ankle boots and a turtleneck

A festive Nap Dress then paired with favorite ankle boots and a turtleneck.

Velvet Holiday Outfit: J.Crew Velvet Blazer + Gucci Bag + Sarah Flint Pumps

Wearing a J.Crew Velvet Blazer + Gucci Bag + Sarah Flint Pumps.

Wit & Whimsy wearing satin trousers

I love satin trousers for being comfortable and featuring an elastic waist band. Favorite pairs of mine include the La Ligne Colby Pants and also this pair by Reformation.

 

Have specific holiday occasions you need outfit ideas for? Over on Substack I curated even more Outfit Ideas for the Holidays.

Holiday Outfit Pieces


 

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