I never know what to wear out at night. It’s different from being out during the day — the vibe of night is always a bit more mysterious, flirty. It asks for a sort of style crank up that could open you up to the unknown.
The thing about this crank up is that it is totally in the eye of the beholder because ultimately, in a city like New York, anything goes, at any time. There is no truly assumed dress code save for just the one: wear what you want.

Mostly I go out to dinner. It’s the pre-eminent way New Yorkers connect and especially during this stretch of real cold, when it’s hard to get feedback from the streets because no one is out on them (see: “city walks,” any of the street reports), these nights out become crucial for me.
The outfits get me in the right frame of mind, they rinse the day off and invite me to appeal to a different, unilateral even slightly unhinged sense of inherent self-ness, where it’s just me and my friends or me and my partner or me. Just me. I love going out alone too.


I do it for the energetic feedback, to take in what the people around me are doing, saying, feeling, thinking.
The thing is, I’m less inspired during the winter months. So I don’t make the time to go through the meditation of getting dressed in the same way. I don’t have the same appetite. Usually what happens is I’ll start in one look and peel back layers from there, adding on new ones until I arrive at the internal place of eager and clear.
Do you know this feeling? Sometimes while I’m getting dressed I’ll start to think: I don’t even want to go! Until I get the outfit right and realize that I just wasn’t ready yet.


If I still don’t want to go is usually a good litmus test on the company and the nature of the plans. But back to the first point: I never really know what to wear out at night.
There are various kinds of dinners that could demarcate your style choices. Let’s break them down to:
chill date night
fancy date night
dinner out during the week
dinner out on the weekend
girls only
solo eating
and work dinners (could be a big dinner or a small dinner, like a catch up with whoever, and somehow the intimacy does impact the look)
I guess the thing that makes you want to look different for these occasions has less to do with where you’re going and is more about who you’ll be with. Who you’ll be with and the different parts of your personality that you would like to appeal to.
When you consider the who and the where, I think you land on this perfect enmeshment of atmosphere and audience to mix into the cocktail of your own personality, and that might make the dressing process easier. Some ideas for me (and maybe you?) based on this principle, to return to the next time I (we!) can’t figure out what to wear.
Chill date night vs. fancy date night
In either instance, you probably want to be wearing comfortable shoes (there may be walking). This principle is further accentuated when its cold out, because a pair of heels cuts off the circulation to your toes, so for a chill night out, I’m going with something like:


I heard somewhere that the further your feet are from the ground (while still level), the warmer they’ll feel.
On a fancier date night, the vibe might be more like:


Dinner out during the week vs the weekend:
The key difference between the two is that on the weekend, you get dressed specifically to go out at night, you know? The assumption is that you’re heading out from home whereas during the week, it is much more likely that you’re going to dinner from a meeting or the office or just a long day that has not afforded you enough space to whip yourself into a look.
On the weekend, the vibe is more…



…Open to appealing to the whims your closet is asking you to. I find that when things scream out to me from the wardrobe it’s because they want to get worn. No better time to play with this than on the weekend when you’ve been home and now it’s time to get dressed to go out.
During the week, idk, do you even want to whip yourself into a look? Me, personally, I find there to be something nice about taking something you wore all day — maybe a blazer, t-shirt and jeans, maybe wooly pants, and making it feel more relevant at night. You can do this so many ways.
Take off the tee that’s under your jacket (and add a skinny scarf), swap out your boots for heels, slap a feather to your jacket. The options are simple and endless (and you’ll see more at the bottom in the work dinner category).



Girls dinner vs. solo dinner
I guess you could conceivably wear the same things to both, although I do think a girls dinner affords you a sense of confidence to try something different or new or even to follow a “sexier” impulse that is unlike what any other context asks for. This is your chance to bathe in the most subtle and extreme qualities of your you-ness. Those that might find you pairing raffia with corduroy or layering fringe or suiting up and jellyfishing down.





The thing about a girls night look is that the dress code basically demands that you ignore the context of where you are and really bask in the freewheeling weirdness of whatever it is that is drawing you lately. This is the best place to take a style risk. The ones I take are often silhouette-based. Less classic shapes like a polo sweater and straight leg pants, more short things, sleeveless things, wild things overall.

Whereas when you’re eating alone, maybe the vibe is actually more akin to when you’re going out for dinner during the week, or on the weekend — whatever. But you’re already indexing in the vulnerability department elsewhere, by taking the risk of exposing yourself in a table-for-one setting and doing it with shoulders broad.



So the outfits, pending your own desire to really feel like you’re leaving home with the kind of excitement that comes through the possibility of the unexpected, are more straightforward with little tweaks: the layers of fringe, an unexpected shawl, shoes that take you out of yourself.
Maybe you do want to go for it, idk, something is drawing me to the simplicity of this combo lately — so here it is for your viewing interest:

Work dinners
The last category. These are outfits you are most likely wearing after the work day, lest you work from home in which case you’re getting dressed to go out with the full range of your closet in front of you. Some include a piece of jewelry (gold choker) or pair of shoes (red heels) you’ll want to swap in, others might be as simple to nail as taking your sweater off to reveal a tank top. (And maybe you’re changing from boots to heels in this instance too; it’s not fully necessary. All contingent on your preference).




I’m personally hot on the tie, and love the idea of pairing a formal one with jeans. The above rendering is more of a “we’re negotiating something at this dinner” look, while the below is more, “I can’t believe you used to be my boss and I’m your boss now. let’s celebrate!”

A good place to land. Enjoy your dinner!,
Leandra
This is one of my favorite outfits edit! and a special love for the Cocteau fish pin :) I would love to see a vintage focus series. Always inspiring. Thank you!
Not going out to dinner these days.