Why does dressing this time of year feel so good?

Outfit ideas for when it’s no longer summer in spirit, or quite yet fall in climate

It felt like a revelation when I realized a few weeks ago that the reason we, uh, professional dressers get so excited to dress for the fall, like more than at the turn of any other season, is because it comes after a two-month break from actually getting dressed.

The cues of summer are always fluid and easy with all the in-between clothes and that’s not even taking into consideration the quality of nudity and lounginess that’s been specifically pervasive in the last two years, so when the parade of new-ins comes dancing through, there is a potent and intoxicating freshness about them. You just want to get in on it, you know? Kind of like having a martini, or a cup of coffee, or going for a run after a long time off. The high of any endorphin-releasing return just hits different.

But then there’s also the thing of pre-fall dressing, which takes place now — during the peak of “Pretend it’s an Editorial” weather (that’s a riff on the Fran Lebowitz doc, "Pretend it’s a City”), when it’s not summer (in spirit) or quite yet fall (in weather). When you can wear an amalgam of summer hits with the fall features you’re most looking forward to (riding boots, no tights and recreational track shorts for example or flip flops with corduroy pants).

Zip and fly will not close, but that’s no prob thanks to my waist scarf. Prada sunglasses, The Garment jacket (this is the same cut), Le Scarf leopard scarf, Emi Mess pants (debated styling with these for a more casual fit) , Flowze sandals, Rabanne chain bag

An alt way to imagine the above look with the scarf tied around my head, a jacket from Kallmeyer, a Marchen skirt, lace ups from The Row (from a prev season, but here they are with a gold stud) and a Nannacay bag. The sunglasses are from my collab with Delarge, the ring is from Pamela Zamore

The correlation with postpartum dressing

It’s not so different, actually, from postpartum dressing to the extent that the principal dressing rule is: take your best hits from the season that just ended (in the instance of my pregnancy, that was: silk button downs, summer “coats,” lingerie tanks, elastic waist knit/silk/jersey pants; in the instance of summer, that’s: whatever you wore and loved most/had on repeat) and update them with complements you could not wear during that season (in pregnancy that was: defined waist lines/belts, all the other stuff that didn’t fit; in summer that’s: cooler weather stuff, like lightweight jackets or sweaters or anything that would make you stickier).

Peress silk tank (here is Doen’s, here’s a teddy that would make tucking in very easy), The Row corduroys, Christopher Esber flip flops and maybe the best clutch I’ve recently encountered — the right size, stiffness and shiny finish to polish off a look that is more relaxed

It can be kind of overwhelming in my opinion to actually get the looks right because so much more of your wardrobe’s terrain is eligible for wearing during the pre-season. You’re working with some of winter, some of summer and all the in-between stuff you probably have that is more fall/spring. Not to mention your outerwear option is often lightweight coat or sweater but no need for both which opens up its whole own world of ways to style yourself. (What a sweater does for an outfit is v dif from what a jacket does bc the footwear chemistry completely changes.)

Not summer, not fall, the looks:

I’m going to try to break this down by garment to work around in the following sequence of not summer or fall looks.

Here’s one employing two pregnancy hits (pants, jacket) I’ve been wearing a shit ton since Joelle arrived:

Kallmeyer trench coat, Flore Flore v-neck, pants that my friend literally bought from the back of a truck in France (you get a similar vibe with these from the Australian brand, Luuda) and The Row’s saran wrap sandals (do you see how these can accomplish the same look?)

Adjustable waistband but can wear higher up now.

And here’s one I’ve been thinking about since way before she arrived, when I saw a woman walking out of a yoga class on 85th street in something similar last May:

The shape and weight of this button down has been feeling so exactly right and fluid the past few months — from the imminently launching All Three. The tube top is Aritzia, the bike shorts are Maria McManus; these also work or here’s an exact pair from Poshmark, the satin mary janes are Chanel; if you’re looking for a pair of MJs, get these.

This tube top has actually been a real key man in both my fantasies about things to wear

Aritzia tube top, Cos skirt, The Row sandals, Khaite bag (or go with her from Savette)

Same look with a khaki jacket, also from Cos

And the de facto circumstances of it:

And here again we have the tube top with the H&M cargo shorts that got me through summer, plus Emme Parsons loafers and a belt from Tresse (kind of reminds me of a vintage Lacroix belt a la A, B, C); the sunglasses are still The Row (get Raybans!)

Scarf life hasn’t ceded either, but I can cut it up a few more ways now

Like, for example, styled as a halter top with a skirt from Alfie, oatmeal cardigan around my waist and Marie Adam-Leenaerdt wedge mules

You know the drill re sunglasses

The deep-V way is still my favorite way to do it though. It’s practical in that it can both conceal a bottom’s waistline or create a new one all together.

Leset’s lightweight cotton trench from the Kyoto collection, Serenity pants - these or these are good too, Khaite sandals that may as well be Tevas and a blue silk scarf to electrify the various buttery fabrics on tap (would you get a Pucci one?)

And it works without pants too — see:

This is also a good way to repurpose a lightweight trench and bring it into the next season. Nackiye trench, Loulou Studios bag, Jimmy Choo sandals (I keep a search for Tamara Mellon-era Jimmy Choo sandals with the fluted heels on TRR, they’re usually very reasonably priced)

Trick is to make sure your coats lightweight enough to appease the pinning and tucking.

Sheer clothes are still very much in rotation but lately I’m thinking about ways to layer.

Flore Flore boat neck, the Heirlome sheer dress, The Row mary janes

And briefs from Kallmeyer

Flore Flore red boatneck, Frances des Lourdes blue tank, Kapsul skirt, The Row sandals (the closest comp; the shape makes for a good winter sandal). When I do this again, I’ll add an oatmeal knit tied over my shoulders

Per the skirt above, it’s great with a structured top too — a theme that started to burst around the spring 2024 shows (last September, see: Tory Burch) and is exploding in a more pronounced way now.

Delarge x Cafe Leandra sunglasses, Solid and Striped top, the same skirt, Gabriela Hearst boots (the wood sole softens them up a bit)

Back to the idea of summer hits, but now — two ways to slice it with a dress:

Heirlome coat, Miu Miu dress, The Row sandals

I love these dresses from Araks too

A. Emery cardigan, Shtor sheer dress, Row comb necklace (but you can get one from Shtor!), Prada sunglasses

This one above reminds me layering’s important because the days start cool but progressively warm up. You want the layers to be convertible enough to tie around waist or stuff in a bag and you want them to be light. This way you’re not stuck in a suede jacket in 85 degree weather (unless you’re wearing it with something tiny underneath it, see: chemise, see: cotton nightgown).

Soeur jacket, Cos sweater, Doen dress (sold out, so try this), Rabanne bag, The Row’s canal slip-on — but I think it’s the color more than anything else that makes this good 

So a sweater or v light jacket should do it. The former does make for a good waist accouterment:

Liberowe peplum top, Alex Mill cargo pants (hands down my favorite pants of the last few weeks) and this is the sweater, also from Alex Mill

Or an accessory to hang over your forearm:

Aligne khaki top, Tory Burch skirt, Khaite boots, Blooming Dreamer necklace

In the flesh last Sat night

Last thing is an uncategorized plain black silk dress styled with a belt notched low on my hips and Chloe’s new clog mules.

Serenity dress, By Malene Birger belt, Chloe shoes

A great dress alt: this one from Ciao Lucia

It’s an extremely practical dress to the extent that you can wear it out-out, is great for like, a parent function at your kids school (if this applies), probably works in the context of a job that has a relatively stringent dress code (give it a sweater, give it a jacket) and falls in the right spot on your legs — about 2.5 inches above knee. (Also makes it good with riding boots, leaving only the small of your legs exposed.) Ciao Lucia has a great one (dress) on tap rn for fall.

Ok, that’s all I have today, except for the combo of this purple shirt and satin coat,

Tory Burch coat, EENK button down shirt, Alex Mill khaki cargos, Flowze sandals

And this brown one styled with white shorts and black wedges.

Sessei button down, CDLP white bra, Dice Kayek shorts, Marie Adams-Leenaerdt mules

Two surprisingly good breastfeeding outfits if you can believe it.

Have a great week,

Leandra