What to wear out when you're not getting dressed up, but want to look put together

Plus: thoughts on reconnecting to your creativity

Going out for dinner is one of my favorite categories to dress for because you’re not specifically getting dressed up or staying dressed down so it hits that sweet spot overlap on the Venn diagram of exciting clothes (which tend to be inconvenient) and boring clothes (more often dependable and chronically useful, unflinchingly practical even though they’re boring).

But because the options can seem like they’re endless (infinite pairings abound), its easy to get overwhelmed when getting dressed and turn back to the last outfit you wore that worked.

Which can be great when you don’t want to think, or when you don’t care about what you’re wearing but do want to know that you look/feel good.

But lately I have been feeling like I’m trying to walk through molasses and starved for something different. A reconnection or something to my own sense of humor, my own sense of youthful desire. Which is maybe a metaphor for creativity: the fluid, childlike energy I long for when I’ve been in the goo long enough to start to believe it’s all taxes and dentist appointments from here. In reality, it’s not even close.

I have known for a long time that when this happens (i.e. when I feel uninspired) is when I work with clothes most effectively as a tool to find my way back to creativity — to the parts I like most in myself. But more and more lately, I’m starting to wonder why I keep shutting down less familiar parts, casting them off as Need to Avoid or Fix or just Make Go Away. There’s a wisdom about them I think I am missing.

Though yesterday I had the small thought, while I was running in the park and thinking to myself that it was amazing my legs could go so fast when just minutes earlier I did not believe I could get them up out of the goo — when my I expanded my aperture and started to see all the people around me as possibly doing the same thing as they ran or walked or just stretched through the park looking for their own will to reconnect that maybe the likable and unlikeable parts are exactly the same thing. Two sides of a coin that is constantly turning, sometimes with our awareness and sometimes without. With that one side at times looking voraciously for the other side, unaware that it can’t see it for the simple reason that it is it.

But the reason you’re here today really is to look at the overlap on that venn diagram of exciting and boring. The very sweet spot between belly laughter (youthful desire) and teeth cleanings.

So when you’re going out and you don’t have to look fancy but you also don’t want to look like you’ve been at work/running around/swimming through heavy syrup, what is the ideal dressing formula?

Venstore sweater, if you can believe it (I’m also into the new “confetti crew” from Everlane) Giuliva Heritage — the unsung wardrobe hero of the season! — jeans, Amina Muaddi platforms or if you’re feeling irresponsible and indulgent, these look like the greatest escape

The most reliable one seems to be: two parts trusted garment to one part unlikely inclusion. Keep in mind your two parts comfort clothes could look vastly different from mine. Jeans are an easy one for this because they’re informal and young. I can’t believe how much this matters to me lately — the extent to which what I wear could keep me young. By which I mean youthful, to be clear. Like can get down and dirty.

I wonder if actually every thought/dressing experiment I’ve conducted lately, which has related to replacing jeans or reimagining the things I wear around jeans has actually been a plea to look more alive — as in full of life.

Here is a good grey ribbed turtleneck — will layer under things nicely, but holds it own well too, Jeanerica jeans (I size up in the winter so things tuck in more easily), Refine belt, Emme Parsons sandals

What you’ll notice with these two looks is that both employ the almost same exact recipe — comfortable knit, reliable jeans, and unlikely shoes. In the first instance, it’s the style of shoe that captures the gaze while in the second, it’s more about the whole ecosystem. With the belt styled over the fitted t-neck especially.

Imagined without heels:

Vince turtleneck, which is a good thing to get for $84 — is kind of chic in the summer with a tank and jean shorts or khaki bermudas too, Chanel pearls (these will do the trick), Brock jeans (these seem to be the best comp), The Row derbies

Courreges sweater tank, Saks Potts belt (I rec this if you’re into the white stitching and this if the buckle is what you like ), Emi Mess pants, Bougeotte loafers

You might opt for a cotton tank top (or t-shirt) with black trousers and suede boots or loafers. In this pairing, I’d say the shoes and pants are your tried and true basics, with the tank as the subtly unexpected pairing. Particularly when it’s colder out and as a contrast to socks and shoes or boots.

While we’re in/close to the realm of flat shoes, here’s a more nuanced formula that works, in particular for day-to-night dressing:

Martin Martin blazer, Venstore sweater, Re/Done jeans, Chanel boots (I’ve always really liked these from Saint Laurent, if you’re a 38…)

Wildcard accessories x basic outfit plus one piece that could go either way.

The big black hairbow and gold boots are the wildcard accessories and the interior look is the basic outfit, with the jacket which can go either way. What I mean is that it can make sense of various different environments — like would work well as a coat over a black tie outfit or this dinner get-up I wore last week.

This one below does the same thing, and I shot it mostly for in the event you’re not an avid pants-wearer:

Khaite leather jacket (this one from Theory gets the job done — just rope a necklace through the collar), Emi Mess vest, old Celine dress, Toteme flats

The leather jacket and interior vest (styled over the knit dress) are what give it some edge (I honestly actually wish I’d styled it with a boxy t-shirt or sweater). And the knit skirt and high socks/flat shoes are the pretty soft addendums that keep it nestled into the day-to-night realm.

Another look with nonpants:

Azi land jacket (something like this is really nice too — and hooded; ditto that this, with FRINGE!), Cecile Bahnsen skirt (maybe this is more practical?), The Row derbies and Khaite red suede bag

The other ratio that works is 2:1 dressy to very casual. Examples:

Khaite jean jacket, 2015 Valentino skirt (this is the shape I’m after right now; fun in khaki to contrast with tights and kooky shoes), La Double J wedges — the light of the season!

Carlota Cahis sweater, here are some checker pants and Valentino heels I found on Yoox like 6 years ago, from this collection. They have a Prada thing going on

And the last look from me for this edish:

By Malene Birger leather jacket, Ines Aquino button down shirt (is particularly ideal for layering under a knit), Mango skirt, Calzedonia tights and Saint Laurent slingbacks

A tribute to my investment in white tights for the season. This is actually also another good work-to-out look because the basics here are pretty basic — a charcoal grey wool skirt with a white collared shirt under a black sweater. It’s really the patent leather sandal/leather jacket combo that gives it a little spice — so maybe if you’re inclined you can try this with commuter shoes and go from there.

That’s it from me this week,

Leandra