The holiday dressing menu, 2023

What to wear in December

December is basically a season unto itself. The post-fall, pre-winter holiday season with its own unique dress code (slap a feather or a sequin on!) and behavioral guidelines (have cheer!), with its energy so overwhelming and seductive, it’s easy to get swept up in it.

It’s also the worst time of year to think practically — to update your style or shop for the bones of your wardrobe, the things you buy to keep forever. This is because it’s a season that is kind of suspended in frivolity, which is fine if you’re a fan of the suspension (see: the shopping section in this multipurpose post) or if you plan to repeat the same menu every year (it works) as far as your dressing recipes go.

But if you crave something else from what your existing wardrobe gives to you (even if just a minor update) and know better than to shop for the tiny season we’re in (hard for me; I’m a true sag), what do you wear for the 34th time you’ve ventured around the sun for the holidays?

If I’m being honest, I myself don’t really know what to wear lately. Nothing feels right, which I mean so genuinely. It’s like I’m clear on the sense I want to touch into but every time I try while getting dressed, it comes up flat, or incoherent.

I labored over the looks you’ll see in this post for a solid 4 days, first slapping sequins and crowns, a dash of red or feathers onto my everyday outfits:

Sequins, crowns, panels of feathers over regular clothes

La Collection sweater, Art Dealer skirt (here’s another fun one), Prada pants from TRR (these are on sale now! And these are a good color match), Doen sandals (have struggled to find similar ones but these could be the closest), Cafe Leandra x Soeur collab bag (charmeuse is coming for us)

Bode crown (not no?), Soeur sweater (this one is good too and on sale), Nue Notes pants (here’s a good wide wale and flare), The Row sandals

This would have been better with these boots. Pardo Hats silk faille headband (worn throughout), Khaite jean jacket (not bad either) and suede boots, Blaze Milano jeans

Maragua Studio poncho, Michael Kors pants (good ref for shape) and Chanel embellished flats, both from TRR

Soeur shirt and skirt (would be so nice with tall boots too), Lisa Yang sweater, Giuliva Heritage pants, Grenson sandals and Savette bag

Lisa Yang sweater (really like this one as an everyday-er on sale too), Emi Mess pants, The Row moccasins (30% off) and my super cool daughter

The slightly more winter appropriate approximation of a weird thing I wore a lot last summer with checkered pants (shape reference), red tights, sandals (here’s a pair in a 7.5) and a ribbed tank. Might I suggest JW Anderson’s boa for your approximation?

But something about it wasn’t right (except for the one time that Madeline snuck into the back of a pic). Not wrong, just…beside the gut feeling. Then I thought that maybe this year it’s more simple than I think. Maybe I just want to look festive.

Unapologetic party clothes

Doen top and skirt, Toteme boots (30% off here)

Plain and simple, no style hacks, tricks or mental frills.

Coziness is allowed tho. La Ligne sweater (the Toteme one is more snug to the body, but the neckline looks great; ditto that this one from &Daughter), Simone Rocha dress (the crepe de chine black version is not sheer, but is $450), three separate belts from Khaite, The Row and Santangelo in that order, and Manolo Blahnik mules I found on the TRR while breastfeeding one time in 2018. I think the endorphins implored me to pull the trigger

Just balls to the walls festive.

Cafe Leandra x La Double J dress, Gucci sandals (a great Prada alt for $175 if you’re an 8.5, Casadei for $60 if you’re a 7.5, Manolo for $100 here if you’re a 36.5, Jimmy Choo for $110 if you’re a 10, and I think these size 9 $84 D&G cutie pies are my favorite of the look)

Absolutely no pants

Inconveniently festive.

Tory Burch jacket, Rachel Comey top (predates Khaite, but still feels Khaite-ish; I love this guy too and this could be great for the holiday season and beyond) and the shoes are Jimmy Choo. I recently saw these on TRR tho. How do you feel about these tights? Or these!

Flore Flore boat neck, Santangelo belt, some swiss dot tights can be found here, Khaite sandals (these have an eerily similar heel, but this is an overall better shape, Savette bag

Perhaps even…deceivingly festive.

Because it looks kind of chill but then you’re fully not wearing pants! Like did you forget them at home or is this on purpose? The suspense is carbonating whatever water still trails through my nervous system. Wardrobe.nyc ivory blazer (this one from Nili is on sale, but I like the shape of this from Toteme), Damernes Magasin brooch, Madeleine Thompson sweater and I truly don’t know why it seems so hard to find a good pair of metallic sandal heels

This look is my fav of the whole loot: Khaite scarf (I feel okay about recommending this one too), Christopher Esber sunglasses, Venstore sweater (try this from Uniqlo), Calzedonia tights (these are possibly even more festive)

Now, I thought, I’m getting somewhere. I can’t wear these looks on the subway per se, but they more acutely capture the spirit I’m after. They reflect the suspension!

I’m craving more fun, even fantasy, and I’m not sure how exactly that will play out but these are the closest passes so far.

Another interpretation includes this Saks Potts plaid scarf, By Malene Birger gloves, a Vince sweater (she’s on sale) and sandals from The Row

Call them a temporary lift off the ground.

Marlies Grace dress, Comme Si socks, Doen black flats (alt option here, or something like these work too). I will totally wear this dress with black pants under it next month

To the final point in the caption above, I just had this idea:

Using a smocked silver dress from Rodebjer (this one for $415 is great too), a strand of pearls, Christopher Esber mesh shoes (we will need socks, I recommend stockings) and the sample of this fringe-hem dickie I wanted to make when Man Repeller did a few product drops, but never produced

Dialed down, but still kind of dressed up

But as far as actually leaving the corner in my living room where I take pics for this newsletter, the formula I find myself turning to most includes something black and mini styled over sheer tights with metallic (or colored) sandals.

The contrast is amplified when you’re wearing all black. Loulou Studios dress (here’s another one that will make for a great but achievable challenge to style post holiday season; I also love this little thing from Khaite). If you’re looking for a personality hat, Jalil Johnson recently turned me onto Amy Downs.

Patou coat (is 30% off), Loulou Studios ‘Mora’ sweater, Annie’s Ibiza dress (for $118, I really think this one can get the job done), La Double J wedges (if you wear a size 35 or 41, they’re 75% off here, if you’re a size 6, they’re $105 here)

Same look, just without the coat and reimagined with a pair of black velvet friulanes (The Row’s version with more coverage are on sale here) and the add of a gold pendant on red thread

Unless I’m playing with longer silhouettes. I like to think of these more as suggestions for what to wear when you want to look like a holiday party host (and will not omit pants):

Heirlome dress

La Collection dress, and as for the shoes, Doen’s holiday mule loot should have you covered.

The headband

But the elephant owning this room is definitely the tight-to-the-forehead black headband, which, in the last two weeks, has turned everything I wear into a holiday look in its own right.

Splendid t-neck (have been wearing this guy since I was pregnant with Madelaur), Rodebjer macrame sweater (mine’s a medium, and speaking of Splendid…but maybe this one from JW Anderson’s better? Or sleeveless from Tanya Taylor here? Or not to change the subject completely, but), Kallmeyer pants, The Row sneakers. These exist too, for a just-as-good vibe

With supporting cast members, like 👆🏻 a long necklace or waist belt.

There is a broader 70s thing going on for sure — you can smell it in the air with all the untreated suede and brown pants/sweaters/coats. The undercurrent of this macro shift must be inclining me towards this one cue pulled from the Bardot playbook.

It’s like instant holiday cool with the simplest looks. I’m talking sweater and trousers,

Loulou Studios sweater (I finally found her! She’s also here in navy or white, or here in red), Khaite belt, Emi Mess pants, The Row sandals (these pony hair fishermans are something too) and Calzedonia white tights (I’m also wearing two pairs of pearl earrings clipped into each ear)

Close up of the double pearls. Kind of like the idea of a black/black and white pair too

T-neck and mini,

I’d actually prefer this look with underwear, but for the sake of acknowledging that we probably won’t actually go out for sustained periods of time dressed like that, here’s a skirt. The sweater is from The Row (I like to call it the anti-touch screen t-neck) and the flats are Doen.

A tunic and nothing else.

Tove Studio tunic

Except red tights and shoes !or pants!

Sir black dress (I also like this from Kiki de Montparnasse for $276), High Sport pants, old Balenciaga sandals (extremely uncomfortable, but what a vibe! Am myself considering these for an alt)

That match. Pants that might the tights. Which is def the other thing.

Tights

If you got a pair last year when we broke them down, it’s a good time to bring them out. They’ve been a good work horse this month, and will prob continue to pull their weight into the winter (though recently, I’m craving other colors).

With yellow and purple in particular. These two pair are Falke, but I sure do like these from Memoi too. And for a different, but fun vibe: there are these from Calzeonia

They’re good styled under non-clingy things too, like corduroys (as seen earlier this week), jeans,

Bode crown, Attersee top, some jeans that are similar and Manolo Blahnik mules

or your overalls:

La Veste jacket (this from TRR is for shape, but actually works as an alt), Carhartt overalls (here in black), some pearls for you too and a great red bag with a lighter attached.

Nice with something sheer over too, which actually brings me to other carryover workhorse — white tights. They work the same way: styled under pants, or with metallic sandals

Calzedonia tights, Flore Flore tank, Khaite belt (does the job) and skirt (I like this from Margiela for $275 in white)

But I have to say, I’m most intrigued by how they look with dressy flats like those grosgrain Row bow ones in the headband series or these satin ones below —

Liberowe jacket styled over the overlay of a Camilla and Marc dress that is over a black Toteme bathing suit. The shoes are pre-pandemic Balenciaga

With bonus points for something sheer things styled over them. (Most of my sheer dresses are actually the overlays of other dresses — if you have any, you should try this!)

Alternatively, you can match white shoes to your white tights.

The same Liberowe jacket is photographed here, with velvet shorts, The Row’s comb, and Prada shoes

Remember when it used to be a thing to not wear white shoes after Labor Day? Lol.

As far as proper socks (as opposed to tights) go, I’m thinking: if The Row’s Spring 24 lookbook had a baby with Chanel’s Metiers d’Art 2017 show

It could be the deranged look of Dec. 2023.

Hello she said in her St. John jacket (merry xmas!) with a black t-shirt styled under it and a silk top under that. The leggings are Lulu Lemon (but I like Alo Yoga’s more; have lately been thinking red — for a brown sweater or camel jkt) and the heels are from Sezane

…Nope, not good. I defer back to pantslessness.

St. John jacket, Rotate sequined halter top, Splendid turtleneck, Jamie Haller loafers

This time with two layers of sequins.

Halter top styled under sequined jacket over black tissue turtleneck

Lately find myself craving an electric pink knit, too. This one from J. Crew is on my mind and so is this one, by Lisa Yang. But maybe that’s more of a coping with January thing.

It’s looking more like all black all the time for these days. But no effort exerted for this exercise has yielded more satisfying an outcome than after I realized I could style a pair of flare leggings under a knee-length straight skirt and call it Alaia.

New Arrivals jacket — it’s the dropped and wide shoulder that makes it so good, but sizing up in something like this or this will yield similar effect; if you don’t want to do jacket/have your top do the work for you, here’s a fun guy from Junya Watanabe, pearls not withstanding! Khaite skirt (works too), Alo Yoga flare leggings, Amina Muaddi platforms (lots of colors here, but for some reason they are like $200 less here)

Save for the moment on Wednesday of earlier this week when I remembered that the easiest and most satisfying holiday dressing recipe is still no more or less complicated than your regular clothes with some dramatic jewelry over it.

Completed Works earrings (not the same, but similar), and here is a one-and-done to capture the neck effect, lest you prefer this more dramatic one from Vivienne Westwood, or with less glitz, this from Coconut Love. If you want to approximate similarly, this is a great strand of vintage pearls, and here’s a lab-grown approximation of the diamantes.

Happy December,

Leandra