Big change dressing

A lookbook of outfits underscored by the desire for a new path towards originality

These lookbook posts usually take like, 2 weeks to make because there’s a lot of stewing. I’ll either have a thought on a dressing concept I want to explore (how to wear black without looking boring, is a khaki anorak the ultimate spring coat), or come nose to nose with a dressing challenge I want to tackle, or find myself toiling at the turn of a new season as I figure out what clothes feel right. In the final instance, which often I realize while I’m actually in my closet trying to dress for real life: dinner out, kids hang, school pick-up, a meeting or — I’m not kidding — my 20-block walk to the kosher middle eastern supermarket on 68th street, I’ll usually start a post then take notes in it.

What is the central challenge, how am I encountering it, what am I pulling for, turning against, can I follow the thoughts that actually get me dressed? How many times do elements of the outfit change before I deem myself ready to go? How do I know when I’m ready? What conditions are contributing to the toil?

Re/done sweater, Area shorts (mine are a sz 26; these are a good alt), red Row sandals (these would be good w socks too), Eldon Portobello scarf, black sunglasses. The pin is vintage (Jean Cocteau), and the necklace is from Alexei Hay. I put this on to wear for an Instagram partner story, wanted the outfit to spark an emotional response (from me); also felt like wearing basic clothes (sweater, casual shoes and socks) so combined these two variables with new touches. Scarf was chosen for color; pin chosen to toughen the sweater’s softness. Couldn’t decide on bottom, was craving flare trousers, put them on, but felt a bit stuffy for what I was after. Remembered these shorts, initially styled them with beige suede mary-janes, but needed something to pick up the red so went to these sandals. They required socks to even out the weight at top. The watch/sunglasses choice is deliberate too. They are present to catch each other (black) and anchor the rest of the look.

Writing this stuff out usually helps me organize my thoughts and almost always also leads me somewhere a bit deeper.

Or I’ll notice a pattern like that every year at this time, I feel the same way. I feel disjointed, clothes are off, something just isn’t clicking. It’s always relieving to note the pattern because it indicates that whatever transition I’m in, it’s not personal. Of course with this early fall in particular, I just had a baby. So maybe a new desire towards different kinds of outfits is a pure function of the change.

But what does that mean? What do I want to look and what is the formula that gets me there?

One part fringe, with a flare arm (By Malene Birger blazer (here she is long); this is something else completely, but so worth consideration and I’ll be damned if this vintage Alaia stays avail) that catches the flare leg (Callas pants — they are as good as I told you they would be!), argyle sweater cinching waist as belt (&Daughter), plus cross sandals from The Row (see here for great $100 alt), Delarge x Cafe Leandra sunglasses. The vibe is: I’m almost 40 but still feel young

Bode jacket, Khaite halter top (gone by now, consider this?), Daily Blue raw denim jeans, Emme Parsons sandals, Rue de Verneuil tote. Here’s one I wore a few weeks ago for the first time and have returned to a dozen times since; hits all the right notes with its subtle contradictions, element of familiarity and the risk factor. The contradictions: a dose of paradox (sandals/heavy jacket; refined jeans, casual coat; going out top, tote). Familiarity: The suede fringe jacket feels signature for me by now so this element just feels like home while the necklaces serve as a bit of sparkle and color and the halter top feels like a new choice, so there’s the risk, (a risk often registers as freshness. It can be unilateral). I keep this outfit in my back pocket when I’m in a pinch but know I want to feel good)

For one of the errant 78-degree days we will get at least once before the chill settles. Ruadh denim jacket, Levi’s 505 jeans, cut into shorts, Khaite boots (w my eyes on these), Rue de Verneuil cruise line tote — the exact one here

Putting in a little more effort and paying attention when I am getting dressed to live the humdrum of my regular days or clocking it when I get excited to see what I encounter on one of my walks,

usually helps me to find out.

Most recently, one thing that comes up is that the right accessories really can go a long way.

You can keep the looks really simple this way — spend virtually no thought on them but still create unique enough dynamics that you feel special in whatever you’re wearing.

Loro Piana hat, red button down here, Wardrobe.nyc ivory blazer, Emi Mess pants, Roxanne Assoulin necklace styled as chain belt, K. Jacques sandals (but as it gets colder, will wear with a pair of gold jazz shoes)

No Name is Needed scarf, Dice Kayek jacket, Gap x Cult Gaia pants, Khaite boots

Loulou Studios coat, Khaite scarf as belt (gone but this is not that diff; the fringe is key, but thats about it), Toteme flare pants, Polo sneakers

Alex Mill sweater around waist, Lido swim suit-as-top (these from Dries, currently on sale, make such a good case), Emi Mess pants, Emme Parsons loafers

Khaite belt, Loewe belt, Mana by Ezgi shell necklace-as-belt; the malachite bracelet is by Vertigo

By Malene Birger top and pants, Le Scarf scarf (around waist)

But the main event is the parade of bracelets — the gold and silver are from Rabanne while the wood is from a forthcoming collab (!); the rings are from At Present (x Jalil Johnson) and Lara Somnez

Dries van Noten necklace scarf, Lisa Yang sweater, Kallmeyer pants, a good alt to the shoes here + a red pouch

Once more with an &Daughter cardigan and ripped jeans

Maybe too subtle, but feels good. Inspired by styling on the Aflalo site, wearing a, what do you know, Aflalo knit with Callas pants, Soeur sandals, Prada sunglasses and some blue opal beads (the orange and blue serve as the fun factor)

This rule is true of a statement coat too.

La Veste jacket, Alex Mill grey sweater, Khaite shorts (or try these!), Dior shoes (or the shape of these is great)

Aflalo coat, Donni white t-shirt styled over black t-shirt with white mens jeans (sz 29) from Jeanerica and “clogs” from Jigsaw

Tory Burch gold coat, with an underlying all black ensemble (these are the pants), red socks, Tom Ford sandals

Another Tory coat — this one still avail, with a grey Donni tee, Nili Lotan pants and Renate Jacob’s silver jazz shoes. Here is a sequined bag that will show you a good time

Once the concept is down and I have ascertained whether I’m breaking down and turning around and somersaulting over a trend or trying to solve a problem, I let the ideas stew. Then as inspiration comes to me — whether just by getting dressed and feeling good or walking down the street and admiring what someone crossing me is wearing, or getting excited about the way an outfit is made on say, an ecomm site…or coming across a look Miuccia Prada wore to take a post show bow, I open the post and jot down the idea. “White poplin shorts with sheer tights and fancy jacket,” for example.

Vintage St. John jacket, Bode shorts, Bally cross-flats

These looks often inspire new looks, or different stories all their own. “Is white cotton/linen styled unconventionally the key to transitional fall dressing?” was the idea that came to me when originally I saw a cotton poplin playsuit styled with sheer tights on Bode’s site.

Skall Studio sweater, Doen cotton onesie, black satin mary janes

Before the recent leopard print post ran, I noticed how many pairs of leopard print pants I was seeing on the upper east side. It wasn’t pure objective acknowledgement that got me to the point of making the post though, there was an emotional spark and curiosity about the encounters. I trust it when impulse tells me to follow a feeling.

Doen dress (or for the forthcoming holiday season, maybe it’s about this), Saks Potts belt, Gucci sandals (alt, alt, alt)

And I trust it, too, when in the end, impulse says, “Eh, let’s leave this one here.”

La Veste jacket, Alfie skirt, The Row’s black suede pumps

In the end re: white cotton and linen/transitional fall dressing — they’re good outfits (I wore 2 of them) but that’s the extent of it.

When I have time (and the desire) to go to my closet while I’m in the process of making these posts — actually try things on for the fun of it, I’m usually looking for a window that makes it feel like I have boundless time. It’s similar to the condition I crave the most when I’m ready to write something big.

When I can make the time is also when these lookbooks, now a list of hypothetical outfits, actually start to collapse into order.

Alex Mill field jacket with an Attersee gold button down polo styled under but over a Cashmere in Love red polo — and there’s a white tee under that. Plus Kalmanovich shorts and Tory Burch shoes

The majority of the hypotheticals end up changing once in practice (this is the part that feels like a moving meditation), and something about shooting and publishing the look will often turn it into mental canon for me, a template to fall back on the next time I can’t think of what to wear.

Same field jacket, white tee and shoes — diff pants (Argent) and the add of a scarf (Eldon) and a belt (Sable)

But no process is more worth clocking than when I’m getting dressed to leave home.

These looks are always the most practical (realistic) because I put them on to live.

Me last Fri: No Name is Needed scarf, Alex Mill v-neck sweater, Brock Collection jeans (try these), Polo socks, Ancient Greek Sandals jellies. Loulou Studio bag, Delarge x Cafe L sunglasses

Lisa Yang sweater styled over Frances de Lourdes shirt, Max Mara corduroy pants (they’re 20% off w the code FALL20, and a newfangled seasonal hero; the color on these if you’re not after black is divine). These are the shoes. Sunglasses are also Delarge! Bag’s an old Khaite, named after Lillith who apparently preceded Eve (of Garden of Eden fame)

What I notice most saliently these days is how straightforward the outfits that feel most right to wear are looking. Pants, shirts, shoes, full stop. Lest I add a coat, or trade in the shirt for a shift dress.

Green Rain jacket (the collar zips on, which means you can wear a tiger print one at your will if that is of interest), Aflalo sheer dress, Callas pants, Ancient Greek Sandals gold slippers

I still go rogue sometimes! Worn to school pick up on Monday. It was a weird choice — same jacket, Sir the Label dress, Gabriela Hearst riding boots (I found them on TRR, eye on these rn)

I’m after a new dressing paradox: interesting but uncomplicated,

Heirlome jacket, Old Stone Trade brooch, Toteme trousers, The Row shoes, Roger Vivier clutch (but this one from TRR is everything)

digestible but original,

Did I up above say that clutch was “everything?” Sometimes I don’t even know what comes off my fingertips. Sezane trench, Cos khaki jacket, Cashmere in Love skort, Khaite boots

comfortable but maybe a little confusing. Mature…

Re/done sweater with pin clipped in, Flore Flore tank, Giuliva Heritage ‘Laura’ pants, and the alt cross sandal once more

with a sense of humor, you know?

Aflalo ‘Fenn’ belt

Maybe these clothes are precisely the result of a big life change, like moving cities or jobs, or losing a loved one or gaining a new one or facing bodily fluctuations. These kinds of shifts occupy so much mental real estate and that really does change what authentic self-expression looks like, or how much time you’re willing to give to second/third-order pastimes, precisely like self-expression.

Then it takes a minute for your confidence to catch up. To encourage you to start exploring bigger risks on that new terrain.

Margiela sequined cap, Lingua Franca polo sweater, Giuliva Heritage pants, Soeur sandals

Or perhaps, really, I’m dressing like this as a response to how literally we’ve approached the pervading cultural flatness of our time — the reactionary “good weirdness” and maximalism that at least as far as fashion goes, I helped grow and mature.

Maybe what I’m yearning actually reflects a less personal big shift and touches on what many of us want, whether we know it or not, as it relates to fashion/getting dressed or not, whether it’s deeper, more shallow, or simply just here: a different path towards creative aliveness.