When the weather is changing and you're not sure what to wear

There's no need to reinvent the wheel

I think I’ve been going too fast. Last week, I showed up at a studio in midtown for what I thought was going to be a podcast recording but in fact turned out to be a cable tv-programming recording. My pace occurred to me then. This symptom — of not reading emails closely enough or of responding to something before I fully understand the ask/commitment/statement — is usually a much later tell that I’ve been going too fast.

The first symptom is always disconnection from my body, but the tricky thing here is that I usually don’t know I’ve been disconnected from my body until I can reconnect to it.

One of the most salient ways that I can tell whether I’m in rhythm or not is when I’m getting dressed — when I can feel the physical sensation that emerges at the completion of making an outfit. There’s a sort of sour feeling that comes up when it’s wrong or repetitive or irreflective of my style, but when it’s good, it feels like expansion.

The clothes aren’t like armor at that point, they’re more like a huge heart-opener. I interviewed a reader named Denise with incredible style who is recently postpartum about what clothes are doing in her life right now (coming soon) and she made this distinction, which really stuck with me. Getting dressed to open up, as opposed to protect yourself.

Forgo The Plan for spontaneity

Anyway, I bring all of this up because last week, as I was getting dressed and thinking about what to make for this week’s newsletter, the expansive feeling came up. (I usually have the month planned in advance, but slowing down also means planning less, which I don’t usually like, but which also almost always serves me because without precise direction ahead, there’s so much more opportunity to touch into whatever becomes present magic.) I hadn’t felt the good feeling in a while, which didn’t mean it wasn’t there, but did indicate that I’d been somewhere else.

I was just wearing ripped jeans and sweatshirt.

Donni sweatshirt, Kule white t-shirt, Citizens of Humanity jeans (I typically wear a 25 but sized up to a 27 so they’d look more like this), By Malene Birger belt, Jamie Haller ‘camp’ loafers (but these r so next on my list)

It reminded me as I was trapped in this cycle of trying to outdo whatever I’ve already done, that I don’t have to reinvent the wheel, or even look that interesting, to feel good. And as the season is starting to change and the weather is getting kinder, it made me think: forget the clothes, look for the feeling.

I like this advice in particular because there is always a moment of destabilization at the turn of a season. For those among us who take style seriously, the length of winter or summer is spent constructing a visual identity that accurately reflects our respective natures and accommodates the practical limitations of the seasons. Fall and Spring are more volatile, or agile depending on how you see it, and somehow as such, trying less feels better.

Various forms of desert boot are interchangeable here — like these from The Row (duh) or these from Brother Vellies (these!) or, these which I saw on Laura Vidrequin from La Botte Gardiane

This outfit has been the most frequent bedroom-chair look over the course of last two weeks (because I sized up x 2, I can wear them high waist or low rise. They are really good the latter way w a peplum like this):

Liberowe peplum top, Jigsaw “clogs,” which I got last Spring and rejoiced in when these presented in The Row’s S’24 lookbook; Deszo tourmaline coconut charm and leather chord

And the interesting thing I noticed (re this being the armchair look) is that whereas when the other fickle season (Fall) is coming, I make myself look more like I have my shit together 👇🏻

…when spring is on the horizon, I tend to dress more laidback, like a teenager. I return to ripped jeans and crew neck sweatshirts and fringe jackets and in-between clothes (pajamas that you can get away with wearing to dinner, basically).

Emotional dressing formulas

The days are longer and warmer, so my yen to go out comes back too. Doesn’t matter what I’m doing, I just want to go. The template I’ve been working with most often includes capri pants (knee-cap leggings) with t-shirts, jackets, and this specific pair of pointed toe mules.

Kallmeyer jacket, two layers of t-shirts from Wardrobe.nyc and Kule, Donni ribbed knee cap leggings (I like the little slit — makes them feel more like proper pedal pushers), The Row shoes

There’s an emotional formula (different from a technical formula in that the specificities of the garments that slot into each part of the equation are less relevant than the feelings they give you) that makes this outfit work to the extent that the knee-cap leggings represent a new trend I’m eager to push forward (spring forward?) while the top is a reliable carry over from the season before. This creates a nice familiarity.

The jacket plays into the desire to embody a more laidback vibe and the shoes are a complete contrast to the rest of the look, but tie in because of the intentional elevation I am trying to strike with the rest of the accessories: pearl chain, hard shell silver clutch.

How you wear the basics of an outfit can make a huge difference. Go to yoga! Meet me at a gala! Don’t change in between.

Pearls/jacket/shoes are the work horse that make this a good night option

Limbo pieces

Something like this gets me going too:

Bode headpiece and jacket, By Malene Birger dress, Renate Jacob shoes

I’ve taken note of all the silk lingerie style dresses (none with much sex appeal) dropping all over the web, from this by Ciao Lucia to the regular range by Doen, the less slip-y iterations from Max Mara. There’s a new stickiness about them as the centerpiece of an outfit that can be transformed by shoes and jacket into whatever the occasion calls for.

Khaite leather jacket (a classic cropped moto works too), Manolo Blahnik satin mules (see also: these)

I love a limbo piece — the kind of item that can become whatever you need it to be (black tie, white tie, beach, dinner, drop off, work, wtvr) depending on what you style around it. Seems like for a garment to fall into this category, it’s got to be flexible, or amenable to different contexts, like a piece of bread that can either be finished with something sweet or savory. For the fashion item, key considerations into what makes a garment flexible: shape, color, fabric.

The ‘Audette’ dress from By Malene Birger, $400

With this dress, the shape is pretty modest and therefore could be worn into various scenarios. The color is neutral enough to pair with anything in your closet and the fabric (silk) can make for great contrast with the right casual companions or live up to its preciousness with, idk, shoes like these (and! a boa like this!) (Should I keep going here? Add these sunglasses.)

Another example of a thing I’ve been wearing — less limbo piece, more limbo look:

Loulou Studio sweater, Aligne denim shorts, Bally shoes (or you can try these)

It’s inspired specifically by a menswear look from Bally’s Spring 2024 show (last September collection season in Milan)

And carries with it an ease that doesn’t require so much thinking, but does present a solid bedrock for getting dressed, which you can either leave as is (sweater and shorts, full stop), or push further with creative accessorizing (hats, pins, impossible flatforms).

Two brooch options here

The how of underwear-as-pants

The last thing: are you really going to wear underwear as pants? If the answer is yes, I salute you for taking the risk, appreciate your camaraderie and want to highlight a few considerations to make it easier.