Fashion Trends

My Holiday Outfit Lineup.

By: Jen Shoop

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I just went through my entire social calendar for December and tried on a bunch of outfits for each. I’ve never been so organized or strategic about my outfits in the past, but there is a lot happening this season…! The only big gaps I have are a Christmas tea, Christmas Eve, and Christmas Day, but I will probably re-wear a tartan dress I bought from Nina Blanc last year for Christmas Day, and maybe my trusty tartan trousers (almost identical to these; usually pair with a black feather top like this) for Christmas Eve? I may cave and buy this gorgeous Damaris Bailey for Christmas Eve. I can’t stop thinking about it and I love my other dress from her. For the tea…I heard that Doen is launching one final winter collection and am wondering if the perfect dress will materialize. (P.S. Doen is offering an extra 20% off their Giving Thanks sale today only — discount appears in cart. This top is now around $80!)

For a holiday cocktails and caroling event: this fab La Ligne skirt (true to size — $25 off with code MAGPIE25) and this J. Crew lurex trutleneck with Aquazzura pom heels (old, similar here). Proof that Christmas doesn’t need to be red/white/green! The pink feels so unexpectedly festive. Throughout all photos, I’m wearing horribly chipped nails (proof of Thanksgiving cooking/cleaning!) and these old Rebecca de Ravenel earrings, but will probably mix up the jewelry/accessories quite a bit and rotate in a bunch of my Dorsey pieces.

For a holiday cocktail party at a friend’s home (attire: festive cocktail), this ALC dress. I styled them here with plain black suede pumps but I think it’s more likely I’ll wear my Dee Ocleppo heels (on sale!) This dress runs TTS. I went a size down from my usual size (I’m typically an 0, but can usually wear an 00 in dresses for some reason) and it’s very snug. I’m debating whether to return for 0.

For a Kacey Musgraves Christmas viewing party (I’ve done this the past few years in different permutations — I LOVE that weird, campy show), contemplating wearing this FUN Alice + Olivia confection. Mesh/voile/tulle have been so in this season and the sleeves are SO fun. Love the rich floral pattern, too. This is a very Kacey look.

For the Nutcracker, I’m planning to wear this tartan taffeta skirt (I took a petite 0) with this mesh turtleneck ($22!) and this Tuckernuck jacket (on sale!). I styled here with lace trim Louboutins (old!), but will probably wear a more practical heel as there will be walking and children involved.

For another Christmas cocktail party on the docket, this velvet mini skirt, this J. Crew lurex turtleneck, and the Marais jacket. I paired with my favorite holiday/festive clutch from Michelle Wilhite (on sale today!)

For Christmas cookie making with family, this HHH nap dress (exact style sold out, but same tartan pattern here in a different style) and this sweater.

P.S. More festive holiday finds here. And, not seen in this post but absolutely being worn, are my metallic VB jeans. I actually have them at the tailor right now to hem them a bit shorter. Want them to be able to be worn with ballet flats.

P.P.S. What are the holiday traditions that matter?

P.P.P.S. Still clinging to the sentiments from this surprise pre-Advent interaction with a classic Christmas carol.

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10 thoughts on “My Holiday Outfit Lineup.

  1. What lovely looks! I have a personal tip for what I call “occasion dressing” — I keep an email draft for each year which includes what I’m planning to, and then do, wear to all of my “occasions” that year. This helps me plan/noodle each outfit along the way, and also serves as a record of what I wore each year (I send the draft to myself at the beginning of each January and then label it before archiving.) I started this practice about a decade ago, during a very wedding-heavy phase of life, and it has served me well! Also helpful in case I don’t want to repeat my Thanksgiving outfit with the same group of people, for example!

    Can you tell I spend a lot of time thinking about my wardrobe?! I promise you, I have always been this way 🙂


    1. Thank you SO much! Yes, it was really helpful. Helped me identify a few holes / strategize which looks I could repeat because of different groups of friends / etc!


  2. HI Jen:

    Love this post! How does the mesh turtleneck from Amazon run for size. Thinking it might be pretty with blue velvet pants! Thanks Marianne

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