Outfit formulas for the holiday season

Welcome to the Thanksgiving-through-Christmas dressing extravaganza

The most intimate holiday parties take place in one of three places during the holiday season: at your place, at someone you know’s place, or out, but with a small group — “out” could mean at a restaurant or some other kind of venue that probably has carpets.

I specify “intimate” in relation to these parties because they seem like the most important ones to dress for — the ones where you actually care to, or straight up want to take off your armor (without physically undressing, unless, live naked!) and connect to the conversation that is under the convo — in the joviality of the season’s spirit, with people whose company you enjoy.

How you dress will not inform whether it is possible at all to unclench and open up in this way, but it can help get you into the right frame of mind. When you’re dressed like an honest version of you that you can both admire and feel pretty proud of, it’s like you become a container that is bigger than you were, open and ready to let new stuff (feelings) in.

There are 3-4 formulas I abide by when dressing for an event that calls for a dress code.

The formulas go like this:

1. Base outfit (e.g. top/bottom) rendered in the dress code in question (so in this instance, it’s “holiday season attire”), extremities (so like, accessories) rendered in contrast (the contrast here would be toned down basics/neutrals):

The sausage making: sequined jacket and sequined skirt at the base, with the plain sneaker boots and oatmeal colored crew neck sweater around my shoulders as the contrasting “extremities” — the socks don’t have to be shiny but why not? Venstore sweater, New Arrivals jacket, Art dealer skirt, APC x Charlotte Chesnais collaboration socks (the Falke ones are just as good), The Row boots

2. Contrasting base (so, neutral outfit), dress code extremities (so holiday party accessories)

Here’s the reverse! A plain sweater (Venstore) and plain pants (these are good khakis! For the fall/winter I suggest a quasi-tapered pair as they pair well with knee-high boots) with holiday season dress code extremities: a velvet hair bow, tons of pearls, a sequined bag, gold boots

3. 2:1, dress code to contrast

Two parts dress code (sheer sequined top — a different vibe, but I kind of love this one? Would look really cool with a basic turtleneck under, tucked into true blue jeans. The one I’m wearing is a vintage Gianfranco Ferre consignment find, but this one from Junya Watanabe is actually pretty close) to overwhelm 1 part contrast (nude ballet flats with sparkle, grey socks)

4. 2:1, contrast to dress code

Two parts neutral extremities (white tee, white jeans, and I threw in a summery leather rope necklace too) to one part holiday party season wear (the velvet hair tie). Then the combo of the black blazer with gold button plus shiny burgundy brogues can really go either way (e.g. mean nothing or everything in relation to the dress code) but in the context of this outfit, bc of the bow and the time of year, embody ~tHe SpIrIt.~ Vivenne Westwood t-shirt, Re/done jeans (I also LOVE these from Jeanerica), Martin Martin blazer, Old Celine brogues (you can find a bunch on this page; it’s this style).

5. And then there is the equal dose of both.

Toteme sweater (I am telling you, it’s the best 1 ever), New Arrivals skirt (here’s a good one too), plus tights that are similar to the ones pictured (here they are in more sheer form) and Louboutin kitten heels (I maintain that these look pretty good). The sweater and shoes are the contrast, with the skirt and tights as the party wear.

Next, you’re going to want to apply your choice ratio to the event you’re dressing for.

For parties at home, my favorite formula is 2:1 in the favor of the dress code — it’s easy to take a risk within the comfort of my own place, and dressing for parties and being home is an entertaining challenge to rise to. Here’s what I wore last Fri night:

Leset tank, LV pants (if you’re looking for good black trousers, I say get these corduroy ones from Toteme), Valentino ballet flats (a v good, v recent Real Real find, but the Loeffler Randalls are good too) and a very big black velvet hairbow from Pardo hats

Another good option:

La Veste flannel jacket, The Row pants, Pearl River slippers

For parties at someone else’s place, one thing is of particular importance to me, which is how the outfit will look with no shoes on, so I dress according to that assumed bar and find coming up with two options — one for pants and one for short things often serves me best.

You get a two-for-one deal by just buying tights instead of socks because you can wear them with short things and with pants. Here’s the link to the lacey tights

And here’s one to some $10 Lurex beauties

For parties out, the stakes are diff. It’s almost easier to consider what you will wear because you’re on neutral territory. It’s easier but doesn’t always yield as poignant a result. The options are many more, and because of this, you might that its easier for decision paralysis to water down what you set out to accomplish. If you’re in the mood to feel good in your clothes, just pretend you’re going to a friend’s house. If you kind of don’t care about what you’re wearing for whatever the reason, you’re in luck! Ppl prob won’t notice much anyway.

Some other recent outfit ideas I’ve had:

I’ve worn this outfit every holiday season at least 1x since 2018 (w the exception of the jacket, which is new and the specific hair bow, which is this giant one) since 2018. The rest of it is: a Peter Som top (out of business now, here’s as close a comp as I could find — a skirt or two for you to pair with, idk, a wool polo? Also, this 3.1 Phillip Lim peplum top seems somehow related and is on sale for $202), Balenciaga’s “knife point” mules.

Not exactly festive for the holidays re the colors, but festive nonetheless? This is the kind of thing you might wear in, idk, Miami? Maria McManus blue button-down shirt (here’s a good, more casual comp), New Arrivals sequined top, Paul & Joe pants (La Double J’s cut is good), Khaite belt, Gucci slingbacks

Polo Ralph Lauren mens flannel shirt (here’s one from J. Crew), a similar pair of velvet trousers (also from J. Crew — but tbh, get the Toteme corduroys if you can, Saks Potts tights and two pairs of shoe options — a gold Old Celine sandal (but any skinny heel pair with an ankle strap and relatively narrow toe should do — I love these from Emme Parsons) and Saint Laurent slingbacks , or these are a bit lower in heel height (…and again, these patent leather guys look pretty decent…)

After putting this together and then running through it one last time before publication, the last thing I’ll say (which is probably also kind of the only thing I’m actually saying) on this topic is that it seems like you can basically make any outfit a holiday party outfit by adding a black velvet bow.

Isn’t that a load off?

Ok! If this is where I leave you, happy Thanksgiving! And also…thank you, so much, for choosing to be here, in these emails, making the weekly, anchoring ritual of putting them together seem to me so worth it.

I have gotten to know a number of you and am blown away by how natural it has been to connect — on the clothes, absolutely, but also on books and recipes and the spiritual matter that seems to be exploding, in one way or another, out of many of us these days.

It all feels a bit like the beginning of Man Repeller in that the promise of a shared sense of humanity — of a lovely relationship — among virtual strangers is reinforced with every comment or e-mail reply that is sent. I love doing this so much and that is 10/10 because of your trust.

No Letter of Rec this Fri, but here’s the gift guide from last week in case you missed it, and I will see you back here next week for adventures in, probably, sweater/pant combos and some thoughts on belts. Thank you, thank you, thank you again.

Signing off yours,

Leandra

And now, your cheatsheet*

*The important takeaways from this post:

1. It is very, very okay to recycle complete holiday looks on a per-annum basis.