on transitional dressing and transitional fashion gossip

Early September styling notes, shopping recs, song suggestions, and scuttlebutt

On Wednesday, driving back to New York City during golden hour from an extended Labor Day weekend in the Catskills, I was struck by a deep sense of melancholy about the unofficial end of another summer as I watched the sun descend over the mountains. Our modern day bard in August wrote, “to live for the hope of it all”, which embodies the sentiment one has at the end of May: the hope of what’s to come during a time when the sun is most shining. But we should really bottle that feeling and drink from it year round. For even though we’re transitioning from light to dark, and even though the world feels quite heavy right now, we can remain hopeful and inspired. And there’s plenty to look forward to in the months ahead: the ability to go for walks - in cute, styled layers no less - without immediately breaking a sweat; having all your friends finally be in town at the same time; new releases in movies, music, books, and the arts; an utterly stacked fall concert season; weekend or longer trips to embrace or escape (depending on your needs) the cooling weather; and last, but certainly not least, all the fashion.

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SCUTTLEBUTT

• Vogue is officially in her transition era with the announcement that Chloe Malle is Anna Wintour’s successor (life *slightly* imitating art as she is the daughter of Candice Bergen, who played Vogue editor Enid Frick in “Sex and the City”). The New York Times reported that part of her vision for the future of Vogue is to have fewer print issues that are viewed as collective editions.

  • As a Vogue print subscriber, I’m totally supportive of focussing on quality over quantity. I hope that Chloe will bring a fresh perspective on cover styling - similar to what Edward Enniful did at British Vogue - and that she recognizes how critical a cover is to the collectible status of an issue. Anna’s covers in the past 5 years have been all over the place; I can’t get over how uninspiring this year’s September cover is.

Two fabulous September issues from 2022 (Serena) and 2018 (Beyoncé) that I’ve held onto and then there is the understyled, underbaked, destined for the recycling bin cover from 2025. Emma Stone deserves so much better!

• A lot of fashion houses are also in their respective transition eras with 15 designer debuts scheduled for the Spring 2026 Ready-to-Wear season. I’m particularly excited about the Proenza boys at Loewe and Louise Trotter at Bottega (and I LOVED Michael Rider’s debut collection for Celine earlier this summer.) My prediction is that Demna Gvasalia is going to make Gucci look like Balenciaga, Pierpaolo Piccoli is going to make Balenciaga look like Valentino - and Alessandro Michele is already designing Valentino to look like Gucci - and we’re all going to wonder why Kering¹ even bothered.

• Jonathan Anderson’s new vision for Dior debuted on the Venice Film Festival red carpet and I have some light concerns about what the upcoming womenswear collection will look like (see, for example, this). Like, Greta Lee looks incredible in the below Dior look but that’s because she is Greta Lee. As my friend commented, on mere mortals this would give circa 2008 going out top.

• Giorgio Armani passed away this week and the retrospectives of his red carpet work made me fully realize his enormous impact on fashion (I will admit that Armani was never up there on my list of top designers.) He designed one of Lady Gaga’s best looks of all time - I would never guess it was Armani - and dresses worn by Zendaya, Carey Mulligan, and Demi Moore are some of my favourite pieces in recent red carpet history. And I loved

  Becky Malinsky
  ’s post this week on Armani’s slouchy suit legacy.

STYLING NOTES

In light of all the transitional wardrobe online chatter, I took some time this week to examine how I can transition my most worn summer pieces to the changing season.

(1) The Tank Dress

Jackets for fall? Groundbreaking, I know. I plan to pair my McQueen tank dress - comfy as hell but also elevated - with a suede fringe jacket that I purchased off Poshmark for the Calgary Stampede (I had it altered to remove the shoulder pads that were a little aggro.) I’ll continue to wear it with the Dries sneakers that I extolled in last week’s écoute, but this look could also work with boots.

If you’re wondering, yes - this coral accent wall was a depths of COVID choice. And one day I aspire to display my shoe collection on something that isn’t a plastic shelf from Bed Bath & Beyond; in the NYC apartment tradeoff matrix, I picked location and light over closet space.

(2) The Shirt Dress

I’ll layer this Proenza cape shirt dress over wide-leg jeans to evoke the slouchy insouciance of Phoebe Philo-era Céline styling. I’ll wear this with flats or heeled boots when the weather turns nastier.

(3) The Long Short

The Leset city short - beloved by me, hated with the fire of a thousand suns by my partner - will not be stashed in storage come September with my other (albeit shorter) shorts; instead I’ll bring them into fall with a crewneck sweater and my new black knee high boots purchased on super discount in the waning days of the Net-a-Porter sale.

(4) The Matching Set

I got a ton of mileage out of this With Nothing Underneath set this summer. In addition to continue wearing it in the fall while working from home, I may pair it with a blazer and loafers for a preppy look.

SHOPPING RECS

• In lieu of shopping recs this week (boo), in this transitional period why not take a beat in the onslaught of fall arrivals and assess what’s really important to add to your wardrobe. It’s very easy to succumb to buxiety and the shoppies during this time, so I use an app like Carted to track items that interest me and build out a shopping list vs. buying everything ASAP for fear of forgetting about something I love, and otherwise I try to wait at least 24 hours if not more before adding something to my cart.

• After a few years of rebuilding my wardrobe for my 30s, I’m generally trying to be far more intentional about purchases, focussing on pieces that address true style gaps. Substackers have been helpful in putting forth frameworks for assessing wardrobe shortcomings; I like the recent post by

  Sogole Kane
  on how to stop buying the same thing (I maybe should have read it before I bought the above black boots, but I think the boot purchase holds up under her framework.)

• Items that are on my mind for fall include black trousers that can be dressed up or down, mixed metal cuff bracelets, and a quality sweater like The Row’s Ophelia but at a far lower price point so I’m not too vexed when my cat inevitably sinks her claws into it. I’m also not unsusceptible to trends so I’ve been thinking about a striped t-shirt like one from Kallmeyer. And maybe an orange pant if the shade and price are right?!

SONG SUGGESTIONS

And, finally, in lieu of a list of song suggestions this week, might I recommend this playlist of songs with an autumn vibe (think a little witchy, a little introspective folk, indie pop, and classic rock) curated by yours truly.

1. Kering owns Balenciaga and Gucci, and has a 30% stake in Valentino.