Lifestyle

Holiday Outfits – wit & whimsy

Holiday Outfit in London

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. All curated by me.

Holiday Outfit Ideas

Below are a bunch of my holiday looks from years past to get you inspired as you shop. And, if you need even more inspiration, check out my post on 12 Outfits for Your Holidays.

Tanya Taylor dress (from last year) / Sarah Flint Booties

Tuckernuck Velvet Holiday Dress

Tuckernuck Velvet Mini dress (size 8) and Ann Mashburn velvet mules.

Similar style here from J.Crew.

Woman wearing a little black dress with sheer tights and black heels on a London street, styled with a quilted Chanel bag.

Tuckernuck Crepe Mini Dress (size 8) // Chanel Heels (look for less)

Veronica Beard Suit (from 2024) // Manolo Blahnik Heels (size up half a size!)

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 

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

Paris Outfit featuring Sarah Flint Shoes and a Tulle Skirt and Velvet Blazer

Sarah Flint Gunmetal Lame Heels

Holiday Outfits: a sequin skirt from J.Crew

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

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.

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!

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

Wearing a J.Crew Velvet Blazer (similar here) + 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 Vince. I wear a M in both.

 

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

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