What to wear on New Year’s Eve

The thing about an outfit — any outfit — is that it’s only gonna work when you feel good in it.

And the irony of getting dressed (when you care about getting dressed) is that even though you’re aware of what you’re wearing, and it might seem like the people around you will be too, they’re often actually just picking up on your vibe — on the energy you’re emitting.

When you feel comfortable and solid, that comes through. When you feel hot and ready to rock and roll, that does too. When you wanted to nail it but in full transparency, tried too hard and lost the plot (maybe you yourself are feeling a little bit lost; this happened to me so many times this season), that also comes across.

So before anything else as far as Sunday night goes, remember: outfits work when you feel good in them.

So first you want to ask: how do I want to feel? Once you know the answer to this, you get to ask the fun question: what do I want to convey?

And then you get more technical and practical — e.g. where am I going, what’s the weather like, who am I going to be with (it has almost become taboo to consider the company you’re going to keep when you get dressed, and in a way I feel responsible for this shift because of how hard I have historically championed dressing for yourself but two things can be true at once! And there’s nothing wrong with trying to capture the spirit of what you’re doing and with whom you are doing it — with trying to level set with your environment. The key is just not prioritizing that over your feeling like yourself).

Which brings me back to the first question: how do I want to feel? Sometimes I forget that this has to come first, that everything else falls into place after it.

All this in mind, with my own desire to feel indelibly like myself, just projecting a little more thrill than I have — a soul yearning for levity when it has felt so heavy. Not necessarily in spite of what is, or as a means to escape it — more as a reminder that the sun rises each day, the looks below go like this:

Dressing for: NYE at home

La Collection dress, Calzedonia tights (the Wolford satin effect ones look like luxury), Gucci sandals (these are fun too. So are these), Gimaguas necklace (this one is cool too), Damernes Magasin rosette styled as waist belt (it comes with the red string and don’t forget, the price is listed in DK. In USD, it retails for closer to $50. Either way, here is another option)

What are you going to wear if you’re hosting? I’ve been wanting to capture the spirit of Loulou de la Falaise at her wedding but like 85% less fussy and that means more white, less other stuff.

So this is what how I landed on the dress with tights and slight red accents.

If you prefer something mini, this from Ref makes a good case. I’d size up for a shiftier fit. One more good sandal choice here. Also just saw this silver bead choker on sale from Jil Sander. Could be good with some red string.

I’m surprised by how much I like silver accent shoes against a pair of white tights — it doesn’t read dated or matronly at all anymore. Or maybe I am now just like, an actual matron. Who knows!

Dressing for: NYE at a restaurant

New Arrivals jacket (here is Blaze Milano’s for $1,385 or 10 Crosby Derek Lam for $595; also crazy about this Lady Day coat in patent leather from J. Crew for $427), Nue Notes bra (found it on sale here in gold for $403; then this is something kind of similar for $347. If you prefer feathers, hello!), Emi Mess pants, Emme Parsons loafers — and the lapis/turquoise rings are a deliberate contrast choice to the rest of the look’s sleek cohesiveness

Part of the reason I love a jacket as part of an outfit is because it gives you more flexibility to take a style risk without having to commit to it so entirely if you realize that your read on the room was off base. Putting this one together I thought: what feels comfortable enough to sit in, to respect the environment I’m stepping into but appropriate enough too if the vibe I’m going for is:

It’s never a bad time to get a good black jacket. If sequins are not your thing, maybe brushed leather with gold or silver buttons (Blaze Milano, $1,106; Khaite, $3,800) are. Or buttons the regular way (Loulou Studios, $710).

“Will Jump on Table if Opportunity Presents.”

If, alternatively, you know there will be no dancing to be had, you might go for something a little more mature, like this:

J. Crew sequined top and sweater, Vince skirt (good option in suede here from Toteme), Calzedonia socks, Bottega Veneta shoes

I call it a commitment to sustaining your interest in fashion and its trends while you honor the unspoken rules of NYE dressing. This outfit feels like the kind of thing you’d wear to a fashion week party if it overlapped with NYE.

And I think the best idea I had recently was to pin the sleeves of my sweater together with a brooch. Will keep drilling down on it until I’m too nauseous to look.

I found a nice brooch option for you here

Dressing for: NYE at the clurb

Flore Flore two-tone boat neck (there are a few on sale at SSENSE), Khaite skirt (gone now, but this from TRR is not a no, this is a good [if not more naked] alt and this one is somewhat conservative but probably the most practical). Skirt styled over sequined tap shorts (from Nue Studio, but here are some goldies from Bode), Kate Cate shoes (further discounted at Baltini here)

You can probably wear this to a restaurant too, but I like it for the clurb because the top is cotton and breathable, and the skirt is styled over a pair of sequined shorts, so if things get heated you can take that skirt right off and get up on the banquet with a sparkler in your hand and wave it around like its 2009.

Dressing for: NYE at your friends place upstate

Khaite jacket (I love this one from Polo too), Partow dress, Alo Yoga leggings, The Row pumps

My actual plan for NYE is to spend the night at my friends house near Hudson and I don’t suspect we’re going to do much other than get cozy and love each other but this friend in particular loves nothing more than getting dressed for a theme (there are often mood boards that accompany her invitations) and the combining elements of life upstate and a sparkly night is a fun challenge to rise to.

Would be cool to test the look with a satin slip skirt like this or this with the jacket worn as a top (as evidenced here). For bag, this is a primo alt from La Double J for $270

I suspect she’ll call for “the rhinestone cowboy.” Leggings under dress for warmth, fringe jacket over for flair, sequins to convey spirit, hold phone (and chubby wool socks) and classic suede heels because they look the best. Probably going to come off anyway. Good thing there r socks in my bag!

The other outfit idea on the docket for this particular trip is:

Bode cropped swing coat, here’s a good grey tissue turtleneck, the Nue Studio tap shorts strike again (and the options are plenty across the commercial web — here’s a pair from Free People, another from Mango and still one more by Maje), this time with Emme Parsons’ perfect black suede wedges

Sequined tap shorts, wool turtleneck, cropped swing coat, sheer tights and barely there but still crazy comfortable (and walkable) wedge sandals. So easy to hang around in this one, and the shoe/sock replacement move might actually look/work better. A good choice overall if I want the vibe to feel more…

“Let loose and shimmy” than “Stay close and smile.”

Dressing for: the trend of no pants

If you want to go the pantyhose route, there’s never been a better time, and the risk is definitely lowest stakes when you’re dressing to be in private — whether that means at your own home or someone else’s. Or maybe a private room at a restaurant or something. So maybe you’ll try something more like this:

Liberowe jacket, Flore Flore grey crew neck, Gimaguas knit bloomers styled over a pair of high waist white cotton ribbed underwear (Hanro) and lurex tights from years ago. These are the best I could find as a comp (and they kind of do the work for you, huh), but actually think I prefer these overall. These shoes are also from Emme Parsons

Which as evidenced by the background, I did not wear to stay home. But I’ll say it again: home is a good place to test a new trend you’re inching towards, to get to know whether you can get (as in feel) comfortable (like yourself) with (in) it (the trend).

Shoes aren’t necessary if you’re staying home, but they do add something fun.

Veronica de Piante jacket (less formal, but this makes a good case), Flore Flore black sleeveless cotton top, Gimaguas knit shorts (I like that they have belt loops) styled over the same pair of white cotton high waist underwear from the look above and Loewe flat lace ups (here’s a pair in size 35 from TRR if that’s you). The sheerness of these tights (from Swedish Stockings) is 30 denier.

I keep styling these shorts with a jacket because it’s kind of like a security blanket — the bridge between complete surrender to trend and still tiptoeing around whether I actually believe I can pull it off.

Another way to get your toes wet if your undies-as-pants curious is to try something sheer (like a long dress or skirt) over your underwear to see how that fares. Think:

The Row hat (here in white, but you know what? I think I figured out a way to make one! Which will present in a send later this month), Heirlome jacket and sheer dress, Hanro white underwear, Chanel shoes (these could work with sheer socks or tights; it’s going to burn if TRR really does file bankruptcy, huh)

Negligee and, again jacket if that security mechanism appeals to you. Styled here is a collarless belted jacket from Heirlome (also does really well with a button down under because of the neckline, and has a wide sleeve, which makes knitwear easier to layer in too) and a slip dress from the same brand, which I think the designer is re-cutting soon. An alternative option is this. Or can even try something like this. (Or for a bit more whimsy, this.)

But I’d recommend a plain dress so you can have more fun with how you accessorize without going too far overboard. Wearing a Marisa Klass pearl and shell necklace here, with a vintage Cocteau fish pin and the infamous knot hat. Amy Downs’ would work too!

Finally, if you just want to wear jeans on NYE:

Flore Flore white tank, Brock jeans (have had my eye on these from The Row, but more approachably speaking, a similar pair can be found here, also dropping in the carpenter style from Nili Lotan), old Celine gold sandals (these are elegantay bobantay) styled with sheer knee high socks.

Easiest, peasiest, lemon squeeziest, most feel-like-yourself-with-the-base-of-your-look-give-you-a-chance-to-make-space-to-get-creative-with-how-you-style-around-it choice.

And the brooch is actually two brooches pinned together; they’re from Kobi Halperin.

No shame in that!

Just make sure to have fun. Happy new year,

Leandra