Item A. What to wear when you want to feel like your clothes are hugging you. This first credit is actually not a credit, but what a shoe! Would you wear them with tights. The tank is from a brand called Chance that doesn’t exist anymore; here is a darker blue striped thing in its place, Beaufille belt, Maria McManus pants (another such hero of the season, right next to these yellow shorts, on account of fit and lightweightiness), Cayumas x Cafe Leandra mary janes

“I’m going to the farmer’s market, but just to walk around.” La Double J x Cafe Leandra top, Live the Process white bike shorts, Cayumas x Cafe Leandra mary janes (I matched the headscarf to the shoes by choosing tones of pale pink and brown that complimented them), Blooming Dreamer straw bag

Caro Editions tank (it is Caroline Brasch’s brand), Sea New York cargo pants (I think the Totemes are the best alt for these; these from Matteau might work too) Havaianas flip flops, and a black Edie Parker clutch with a lighter attached. For some reason, every time I have put this outfit on this summer I have felt most honest. Unimpressionable, laid back, kind of feminine, but also cool and ideal to loiter on street corners while waiting for a camp bus full of my kids to return to the city

Caro Editions tank is the bridge, Prada skort from last year which you may remember because I went through a phase of advising you to wear bike shorts under mini skirts and dresses. Did you ever do it? I did. Grenson sandals

This is what I look like while I’m grinding my teeth. The vibe is: teenager meets middle-aged divorcee wearing the earnings from the split. (But the pictured “earnings” are mostly from Dorsey)

Oh, it’s the same look! I’m not the best editor, but this bag alternative required its own caption. The rest of the look is a rigid white t-shirt (Cos and Uniqlo make the best ones), Levi’s shorts and Doen sandals.

The Doen sandals are the bridge between the one above and this, with an Attersee top and skirt. Wear it to your kids’ graduation next year

Kind of fudged this one huh, more like a bridge color palette than anything else with a fancy white single-breast jacket in ivory (not bad) and more Attersee in the shape of silk pants. I’m compelled to suggest these cornflower ones from Vince as their alternative to match a blue button down you probably already own and to contrast your suede fishermans

…The key man of this transition! Styled for a day out, clocking in around 83 degrees F with a Tory Burch skirt and vintage t-shirt

Here it is again, with a vintage Chanel jacket, Caro Editions pants (the companion piece to my tank) and Cariuma sneakers

“Plays soccer once.” +1 for the canvas sneakers with an Abitu top this time and Suzie Kondi shorts (unsolicited 5-star rec for the open hem sweatpants too — size up x 1 for maximum comfortability).

Abitu top, Soeur x Cafe L shorts (saw them styled on @Courtneygrow with a paprika-red sweater, which I’m going to copy), Renate Jacob wedges

Nafsika Skourti tank (still a big fan of this), Doen shorts (this is the shape in a dif color; I like these too) and the bridge to walk over and in: Renate Jacobs wedges

Same top (comes like this too), Matteau pants, Jamie Haller sandals

So the “baby hairs” you inherit postpartum never go away, huh? Caro Editions tank, Matteau green pants, Christopher Esber shoes, Savette bag

If you live in a quiet, conservative neighborhood, this is a great outfit to wear if you want to both blend in and gives your neighbors something more interesting to look at. Sessei button-down shirt (dropping in a 5-star rec here too) Caro Editions tank top, Miu Miu underwear and it’s never too hot, too cold, too anything, I guess for a pair of socks with sandals.

Miu Miu underwear as the Queensboro bride (Area’s do make a spicy case for comp) with a Cos boat neck and Shiloh Heritage boots. I’m so invested in their revival.

Timed nicely with the fringe jacket’s foray into front-of-closet, no? But for this time they’re styled with a bra top (maybe?) and a skirt from Azi.land which I cannot wait to wear with a cropped black jacket, sheer tights, and boots. I’m kind of craving a pair snug to the calf

Khaite bra is the bridge in this one, styled under a vintage sequined top from The Real Real (one of us needs this leopard Dior polo for $168 but here r two potentially more practical alternatives) with Caro Editions shorts, Wolford socks and Jigsaw suede clogs. Raw footage of an actual outfit I wore to have dinner with my father-in-law.

This was the original bridge, before the in-law look, and connects to the next look through the cotton Doen shorts. Connects above too with the socks and bra, huh. The loafers are Jamie Haller

I was trying to get some light from out the window on my face but in the end, I just look like I have a stiff neck. LMND top, The Row belt (I saw this one in the window of an Alice and Olivia store last week and thought it made a good case) and shoes, Doen shorts

This is the look I made to remain consistent in the toss-off (with the pink LMND shirt styled under the brown one the Bottega way), but the real one that got me, as a former Yeshiva day school student, excited about interpreting this skirt a new way was:

This basic pairing. I call it: Rosh Hashana lite. (With Valentino heels I bought from this weird Groupon-esque designer shoe site at least 6-7 years ago (here, if you’re a size 5, and here if you prefer to tango), a Loulou Studio skirt (this one is a nice wash and I like how this one is styled) and Soeur button down — it is the best one for more formal occasions when you want something less fluid than LMND’s Chiara) but if you’re good on a white button down, this khaki number caught my eye while doing this market

This was supposed to connect to the look with the pink shirt and black shorts on account of the shoes but the denim skirt interrupted our flow. Other artifacts include: Gabriel Forsach halter top/sarong, Soeur pants. The little black clutch and choice of “mature” jewelry (speaking of which…) were meant to offset the playfulness of the outfit.

Creative license taken with the toss-off garment as more like a toss-off print. Soeur mini dress, By Malene Birger wine bag. Jamie Haller ballet flats

Any black tube top/bodysuit/swimsuit will do; Emi Mess trousers, French Sole ballet flats, Nili Lotan wallet clutch thing. A good bet for a leather cord to wear around your neck.

Here’s a great comp for the bag — I’m wearing a plain black swimsuit and A.W.A.K.E Mode skirt from a few years ago (this is nice; the current stocked-on-the-big-platforms version of it is this but if you’re going the way of a straight skirt, maybe this Prada number from Resee is more appealing to you) with Jamie Haller ballet flats. They are pretty in this new shade of gold too

Maison Cleo dress, Ancient Greek Sandals. Our bridge is the necklace! A great look for date night. The shirt-around-waist doubles as a belt for the kind of occasion when you’ve been constipated for days but can’t not wear the dress

In the realm of things I’d wear this to the office (if I went to) one on my morning after (if I still had morning-afters): Leset tank top, Max Mara nepeta trousers (o! They come in red), Ancient Greek Sandals, and here is a good belt

Dries floral choker (hold on what’s this?) — it seems so impractical and is annoying to store, but I actually wear it pretty often, Leset tank top, Giuliva Heritage jeans, Manolo Blahnik sandals

Part 2 from the series I’m Going to the Farmer’s Market but Just for A Walk. Etnodium dress, Giuliva Heritage jeans, Havaianas flip flops, Blooming Dreamer bag. Think I mentioned this last week in post but it turns out the ideal-sized bag is about 1/4th narrower than a classic LL Bean tote and maybe an inch or two longer.

Not pictured: the bridge tote. Styled with a Siedres top (might be better as a t-neck! Has a matching skirt!), Jamie Haller loafers

And with the right change of shoes, this one could be a wedding guest look. …Anyone? Siedres sequins, 🤝 we meet again, St. John jacket, Attersee pants (has anyone tried these?), flip flops

St. Agni knit (looks better with a bra), Sable World belt (an alt), Dries mens shorts (these could be good; and suddenly these raw denim shorts seem like the best ideal for fall with that khaki Soeur shirt I linked above and those snug-to-the-calf boots I mentioned), The Row sandals

Another plot break: one unsung hero of second-half summer dressing has been the pairing of things that hit right above or fall right below knee length with lace-up sandals. LMND shirt, Khaite skirt (dropping in the vintage Prada one once more), The Row lace-ups (I still love these)

The tie-in’s in the tie-ups. Should I test them with socks, or too far? The tank is from Caro Editions (the pink one is darling too, huh), the skirt is Saint Laurent (here is a longer mesh version from Good American for $75), the bag is from my collab with Soeur.