It's The Most Metropolitan Time Of The Year!

The Upper East Side is trending. What this resurgence has to do with fashion and the holiday dressing ideas it's inspiring.

Thank you to Bloomingdale’s for underwriting today’s newsletter, making it free for everyone. There will be a few pieces sprinkled into the edit from their 59th street store (how fun and easy is that!?) All ideas and selections are of course, my own.

Pillaging the new designer dept. at Bloomingdale’s. Liberowe jackets!!! Paco lace! Toteme shearlings!

The Upper East Side of Manhattan is trending. So says the Wall Street Journal. And Town & Country. And Puck. And Cultured. And TikTok! There are a slew of new hot to trot restaurants in the neighborhood where you either have to be a member or know someone to even get close to a reservation…yes, I’m looking at you Chez Fifi! No, I haven’t managed to go yet.

The trendiest of brands are staking their claim - Toteme and Khaite opened across the street from each other earlier this year on 69th and Madison and almost daily I seem to pass a new storefront under construction. I have been getting marketing pitches from brands dubbing this the year of the “Ralph Lauren Christmas” from…NOT Ralph Lauren! Not to mention the line for coffee at Ralph’s in their 72nd street flagship wraps around the block Every! Day!

Bloomingdale’s (the sponsor of this newsletter, pinch me!?) is getting a major glow up, too. They’re bringing in brands like the aforementioned Toteme, impossibly cool party jackets by Liberowe, and their shop-in-shops seem to all be getting facelifts…Chanel opened a two-story “townhouse” within the 59th street store and Chloe is under construction just down the hall.

Honestly, thank goodness Bloomingdale’s is bringing it.

When I talked to friend of Five Things Dani S. about the institution’s plans to dig in their heels in the face of so many other department stores fizzling, she got emotional about her time spent there as a kid with her mom and grandma. My husband, who grew up blocks away, jokingly calls the store daycare - climbing under the racks a childhood rite of passage for every kid in the neighborhood…I wonder if kids do this anymore in the age of iPads!? Heck, I registered for my wedding there…still use that Bernardaud china everyday (now they even have Ginori, shoot!!)

Where else can I go to get my son new shoes, a frozen yogurt, a suitcase (our storage unit flooded, don’t ask…but the upside is Bloomingdale’s carries Rimowa in store!) and my favorite sheer socks all in one go!?! Needless to say, it deserves to be part of the fabric of the UES and so as our neighborhood gets it’s next moment in the sun, I’m thrilled Bloomingdale’s is coming along for the ride.

What does all this have to do with holiday dressing? Well! Since you asked, while the conversation around this traditionally “very fancy” neighborhood is abuzz, so are the style tropes associated with the last time extreme wealth was in the zeitgeist (hello Wall Street, Ralph Lauren, Versace!) I won’t get into the good, bad and ugly of these parallels since we are all here for a joyful Sunday morning look at fun things to wear. But I will happily dissect the fun I’m having lately with the mish-mash of 1980s yuppie staples like oversized trenches and traditional knits, “ladies” executive style (Baby Boom!): big shoulders, knee legnth skirts, sheer pantyhose! And the glam/punk/rock thing we are seeing from brands like Valentino and Saint Laurent.

A still frame from Metropolitan, the best Upper East Side holiday movie there is!

It’s all there. And there is no better time to experiment with all this volume than when you were already planning to get dressed up. So below, five style tropes making a comeback and how to wear them in a thoroughly 2025 way.

Traditional Knits

Traditional knits can kind of mean anything, but for today’s purpose, I’ll specifically be talking about the patterned weaves of knits trendy in the 80s. Fair Isle and Native American geometric patterns popularized by brands like Ralph Lauren (props to Polo for their TÓPA collaboration - more on that here). Especially in bold or pastel color combinations and slightly oversized fits, these sweaters are everywhere this winter. For the festive season, try them with a juxtaposing pattern or swap out your silk “gala” pants for a velvet version. It’s the “prep” of the style paired with something a bit more dressy that gives it it’s “vintage” edge.

Ralph Lauren x TÓPA sweater (2nd floor at Bloomingdale’s) paired with a mismatched Aflalo gingham column skirt a Stella McCartney trench in a size 42 (4th floor at Bloomingdale’s or here for ref), Valentino bow pumps and a big bow in my hair which you can’t see.

&Daughter fairisle sweater (size small it runs huge!) with Emporio Armani velvet flouncy pants (4th Floor at Bloomingdale’s) and The Row pointy pumps. Something about a heel with these pieces feels so old school and yet totally new?? A clash of ideas that somehow come together. And just as cute when you take off your shoes at a house party.

Two outfit ideas that feel both a time warp and perfectly right for today, tomorrow and next Saturday: Joes oversized navy trench, this black one from my favorite Korean brand is on super sale, High Sport pink sweater, Alessandra Rich tweed column skirt (on sale!) and Le Monde Beryl boots. Outfit two: Apiece Apart coat, &Daughter sweater, Matteau shirt layered underneath, Toteme extra pointy pumps and Cos velvet pj pants

Big Shoulders, Little Waists

The proportions of the eighties are coming for us. Dramatically on the runways…and as grand or toned down as you’d like IRL.

On a collarless jacket, I like just a little drama in the shoulders, but not so much so that I feel like I’m in a costume. In fact, I’ve been buying up vintage Bill Blass on TRR lately and taking the shoulder pads out while NOT taking the actual shoulder seams in - the slightly wider frame reading slouchy and just slightly boxy without them. I recommend it!

With a blazer, on the other hand, we can go a bit bigger (I’m looking at you Alex Eagle!), tamed by a slim jean and boot on the bottom. The thing to keep in mind for all of these jackets, is to not lose your waist all together. It’s what makes this whole silhouette elongating! Also…a heel won’t hurt.

My new obsession, Maria McManus’s magenta wool jacket with a teensy shoulder pad. Wearing it here with my vintage YSL corduroy pencil skirt (what about this or this?), The Row pumps, sheer tights and a very 80s white sequin chain bag from Chanel (4th floor at Bloomingdale’s.)

Another pencil with a very different jacket that accomplishes the same proportions. Tory Burch crushed velvet floral skirt with a red and white tweed bomber jacket from Giuliva Heritage on top. You can blouse the bottom of the jacket to get that same big on top, narrow on the bottom framework. And of course, sheer tights and slingbacks. This jacket is quilted on the inside and I happily wore this with no outer layer on a recent 48 degree night. Would also look great under one of those oversized trench coats.

Three more ideas in this vein. Left: Rony Kobo jacket (2nd floor at Bloomingdale’s), Aflalo jeans, Valentino pumps. Middle: Alex Eagle blazer (here is her J.Crew version), Christopher Esber skirt and Cabana woven clutch. Right: Maria McManus jacket (so nice I put her in here twice!), Donni taffeta pants and Valentino bow pumps (on super sale! FYI they run big)

WHAT WOULD AN 80S THEMED NEWSLETTER BE WITHOUT AN ARMANI MOMENT!? I beelined to this jacket on the 3rd floor at Bloomingdale’s when I went to pull ideas for this letter. Swoon! This one is also AMAZING and on sale if you are looking for something a little less…loud. The pants are old Kallmeyer (here and here for great alternatives) Repetto jazz shoes and a vintage Judith Leiber bag

The Girlishness of It All

My son has started calling pink things girlish. “Yuck, that’s girlish!” He’ll say. I LOVE the term and use it as much as humanly possible. Pink…girlish! Polka dots? Girlish! Lace! Girlish!! All of these flirty elements mixed with a little bit of prep (blazers, loafers!) make for a very festive party getup. In fact, after all is said and done, I think this is my favorite category!

A textured silk power suit from Giuliva Heritage paired with off the shoulder lace!!!!! This Paco Rabanne top is going to be my holiday piece de resistance. This particular one is from the 4th Floor at Bloomingdale’s. Its also on their website here. And here if the studs are too much for you. Back to sheer tights and slingbacks (are we sensing a theme yet?) a HUGE belt from Streets Ahead and Ray-Bans (Breakfast Club forever!)

The dress that launched this newsletter! I saw this Delphine dress in the window (on Madison, naturally) and then had the tab bookmarked for over a month itching for an excuse to try it. Quick someone invite me to a party!! I layered it here with Khaite’s sheer pink top from this newsletter and it could use some pearls too, now that I think about it.

For those of you wintering in warmer climates…how about this cotton polka dot set from Posse? I will definitely be bringing her on vacation in Jan. In the meantime, I’ll pair her with a black turtleneck, opaque tights and likely boots instead of these loafers. Oh, and a chain belt!

More girly details that feel fun without going too TOO overboard. Clockwise from left: Delphine dress, a string of graduated pearls, Paco Rabanne top, Giuliva Heritage skirt, Co pleated top, Sophie Buhai hair bow, Chloe polka dot pencil, ALC polka dot blouse, Alessandra Rich lace gown (on sale!) Valentino cocktail dress (🙃WOW!), Valentino beaded needlepoint bag, Streets Ahead belt, Roger Vivier pumps (5th floor at Bloomingdale’s)

Desperately Seeking Susan?

Just to take us off the UES for a hot minute here, there is an over-the-top, rock and roll undercurrent in a lot of what is out there right now, when you put it all together. Ruffles and studs and lace and animal prints all layered with leather and chunky metal hardware. It’s a downtown vibe for sure, but still inherently 80s. And while it would be impossible for me to encapsulate all of this in one measly little section one letter, I’m going to do my best to pull of the concepts that feel doable for today without going too time warp. Some December evening ideas (from most to least dramatic) that incorporate this general idea below.

Versace’s orange studded jacket as top (4th floor at Bloomingdale’s) with my old Khaite zebra pants. These or these work! Gold strappy sandals and a gold chain bag. Yowza!

A slew of pieces that if put together do this right, for right now! Clockwise from left: Caro Editions polkadot dress, Isabel Marant studded jacket, Simon Miller zebra pants, Maria McManus silk dress, Valentino brown chevron crossbody (and on the 1st floor at Bloomingdale’s!), Swedish Stockings lace tights, J.Crew flouncy plaid mini dress, Versace studded jacket and skirt, Khaite cowboy boots

More Crossing Delancey than DSS but heck…we’re below 14th street at least with this outfit! Maria McManus silk dress under a TWP beaded cardigan, Dehanche belt and Khaite boots

And lest this entire newsletter get way too out there for you…how to do victorian-punk with jeans and a long sleeve t-shirt!! Consider it Adam Ant lite. The jeans are a new purchase from Aflalo, I still need to get them hemmed but in the meantime, I don’t mind the cuff. (I sized up to a 27 and very content with my decision.) Colleen Allen long sleeve tee and Khaite boots.

A BIG BALL SKIRT as defined by the jacket you pair it with

This category is pretty much self explanatory, and if you have my Holiday Things skirt from last winter, you already know the ten thousand lives a puff skirt can live. But it never gets old and its still on theme, so we’re bringing her back out! Plus, there are a few new good options (if you happened to miss out on last years. :))

Three jackets that change the occasion with my old red taffeta skirt. From left: Liberowe (4th floor at Bloomingdale’s), Polo (2nd floor at Bloomingdale’s, and here), and Sportmax

Five fantastic jackets that pair perfectly with a puff. From left: Alex Mill, Arma (also late add but this amazing bomber, turned on to me by Jeana Sohn herself, is on sale!), Khaite (on sale!), Liberowe (4th floor) and Polo (2nd floor)

From left: Simkhai strapless dress (the long sleeve version in black below!), Suzie Kondi taffeta skirt, Talbots (our favorite plaid ball skirt lives!), Toteme, which I included for the fantastic waistline and a Carolina Herrera dress I couldn’t resist

This Simkhai knit dress is so comfortable, so malleable and so fun I think it will get a lot of wear this season. I wore it once already when my 5 year old wanted to play restaurant at the dining room table and told me to “Wear something fancy.” It felt like PJs! Here with my favorite red heels, white tights and a bit silk bow. At left with an old Tory Burch velvet jacket (here’s a great alt from J.Crew…honestly, maybe even like the sea glass green better!!)

Here she is in the wild.

Bring it on December, we are READY! Meet me at 40 Carrots. I’ll be waiting.

Yours TRULY,

Becky

And big love to Bloomingdales! <3