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Fashion

Americans Do Office-To-Party Dressing Better

Taylor Reed
Last updated: November 8, 2026 3:17 pm
Taylor Reed
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Today’s newsletter is underwritten by Tory Burch. All ideas my own.

I found myself nodding along when reading a newsletter that substack served to me on instagram recently. Such a great headline: Americans don’t dress badly, we just lead unsexy lives. This hit me just as I was trying to put my finger on why I enjoyed getting dressed in Paris so much this season and why I haven’t wanted to wear those exact same outfits recently in New York, when I’m doing the same things, mostly. Not that I don’t love to get dressed here, I do! But somehow I want to have more of an element of daytime-ness in my clothes, no matter what time it is. Not so done up that I stick out, because people here are generally…just less done up.

All cities have their own style undercurrents, though. Milan is extremely Milanese when you start to really look around. Full skirts, cropped pants, chunky soles. And Paris is extremely Parisian: slim jeans, slim boots, blazers and a scarf. So I started thinking, what clothing makes New York style its best self?

A pastel corduroy pant (wearing a size 6!) feels classically American sportswear to me – a little bit utilitarian, a little bit feminine. Worn with a Simone Rocha taffeta black top, they’re cocktail ready. I love the sharp black of the top with the peachy shade of the pants. Paired with brown pumps, a pastel brocade bag (stored in your laptop tote on your morning commute) and simple “diamond” drops to make this more of a full day ensemble

It wouldn’t be right to call the undercurrent preppy – that really stems from old English ideals and has also been reinterpreted by both New England and The South. Or similarly, the idea that New Yorkers just wear black feels like a silly cliche. So what is it?

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I find myself stopping for a second glance when women look super put together and super unbothered all at once, but definitely DRESSED. Similarly, I am the happiest walking down the street when I’m in some sort of nod to the classic idea of sportswear – the category that came of age, primarily, to address women entering the white collar workforce en masse. It’s the Claire McCardell —> Bill Blass —> Isaac Mizrahi of it all which evolved into the Marc Jacobs —> The Row —> Tory Burch —> Khaite of it all!! Coats and jackets that look tailored but not stiff. Dressy clothes in soft colors that take the edge off. Great looking skirts and dresses you could climb stairs in. Pockets! Clothes that could take us into a variety of situations without feeling overwrought in any.

The shapes of American sportswear have evolved over the decades, of course, like fashion on every continent. But what remains is this idea of a woman who lives many lives within the confines of a single day. And that to me, is supremely American. So it makes sense that we challenge our clothes to last us through the twilight stretches of the office holiday cocktail all the while looking perfectly at home on the morning commute and during meetings all day. And it also makes sense that we talk about this American way of dressing during one of the hardest dressing seasons to accomplish this goal: the event-heavy, holiday crunch.

A pastel sporty nylon dress all layered up like a lady. My sheer Prada overlay (38 here, 40 here) that is proving to be a very fun and dimensional purchase (look, Simone Rocha has one too! Or you could cut the lining out of this I bet.) Blazered and bowed (shoes, belt and bag by Tory Burch) and finished off with some “diamonds.” My Dorsey necklace and Bauble Bar drops are constant companions this season.

Use pastels to temper party pieces

The first thing I thought of when puzzling this weekend’s challenge together was the idea of pastels. Soft colors are inherently “sportswear” to me, much in the vein of the powder blue bathroom of my grandparents’ home. Could incorporating them make our evening elements feel more at home during the day? All signs point to yes…

You don’t NEED a dramatic, sheer, black overskirt. You could just belt your blazer instead. I bought this (my favorite) +J/Uniqlo blazer at the height of covid lockdowns and thought, but what if I never wear a blazer again!? 😆 Here and here are simple, non-eye-wateringly priced blazers that can act as your mainstay. If you’re under 5’4” you could do Theory but for you tallies it might be too shrunken.

A blazer (old oversized Row conquest), pastel button down and brogues make a sparkly skirt feel more at home in an office. This particular skirt is actually a party dress. In the evening, you could easily unbutton the collar of the shirt two buttons to relax the whole thing.

A sensible bag makes for a winning night

This pastel-hued thought was followed closely by the word SENSIBLE. Can’t you just hear your chic grandma in a little cape and ballerina flats using this word? This manifested for me in the form of a mid-sized shoulder bag. For some reason, I was (and am) extremely drawn to this bag while starting to gather both my thoughts and the clothing for today’s letter.

I kid you not I read this AFTER writing the paragraphs above and I am shook. From Clare McCardell’s What Should I Wear. I am her. She is me!

Sensible bag, cute outfit, sardine packed on the subway on my way to dinner.

I THINK it comes back to this idea of a sensible bag being the balancing act for wearing party-appropriate clothes during the day. A mid-size bag that fits comfortably over my shoulder all of a sudden makes a feathered skirt feel workaday (in a good way!)

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But sensible doesn’t mean basic. This roomy bag is covered in little metal knots (that I’m told were inspired by a cushion from Bunny Mellon’s Antiqua home – HELLO SPORTSWEAR ICON!!! I KNEW I WAS ONTO SOMETHING!) that give it charm.
**Editor’s note: Obviously this spurred a deep dive and THIS is the house that Tory bought, restored and found said cushion, OMG.

Three more I adore! From left: Khaite (you gotta click this one and see how thin and supple it is at all angles, I’m telling you. A smaller version in grey is also good.) Cos’s great take on eel skin and Kallmeyer’s magazine bag which feels like a blast from the past in a wonderfully new york vintage kind of way.

Use texture to dress up black and white separates

But back to the outfits. With zee fun+functional bag securely in the forefront of my work-to-party-wardrobe, it’s time to get back to layering. Let’s start with some black on black layering (a comfort zone for many of you) and how to snazz it up. Might I suggest your favorite black skirt (maybe one with some flair), a black cardigan and a white button down and then mess around with how it’s all layered. Can you unbutton here or there? Intentionally untuck? Add some texture or shine in one of the elements? This lurex cardi could be great with a white silk tee for example!

A slightly bigger bag makes this party skirt feel less overdressed. Plus a waist cinching, slinky cardigan, (or just a simple one unbuttoned at the bottom or this one that I would really only ever button the top button but interesting!) a white button down shirt or silky tee, sheer tights and pumps make this a go anywhere, anytime ensemble.

With a sharp coat. YA!!!!

The Knee Length Personality Coat, A Sportswear Icon

It wouldn’t be holiday dressing if I didn’t offer up a coat. And man did I find a dream coat when doing my Tory edit. It’s got sportswear written all over it with its velvet details (we discussed the inescapability of velvet last weekend) taking it easily into evening. The little shawl collar is neatly tucked into a more tailored construction. Covered buttons!!!!!

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All my favorite things. A perfect coat. White chinos. My favorite walkable pumps. Diamante earrings, a bow in my hair and now this silver bow-covered bag.

The sharp lined look of a straight, mid-legnth coat in a fabulous fabric is a key feature of (my personal interpretation of) American sportswear. It’s such a New York thing to make coats your full personality – the season being filled with events that you’re popping into, and never even removing your outer layer. So while the black one above is my pride and joy, I am also here for all the brocade and satin and tweed we’ve been talking about already this year.

From left: Prada’s CBK tribute that is the last thing I see at night before I go to sleep. Callas’s white/black cheetah is SO New York to me. It’s cotton so might not make it all the way to December (but maybe? El Nino!) but I own this and have been wearing quite a bit lately. Prabal Gurung’s unique empire seam on pastel floral brocade is a yes! St. Agni’s white floral (similar to Kallmeyer’s below) and Frances Valentine’s cheetah in “pony” for the best price in town. I might hem it slightly.

If you’re not going to take off your coat at said soiree you could just do your favorite black pants and crewneck sweater for the office (toteme and aether respectively) and throw on your hero coat as you head out the door!

Swap your jeans for chinos

Now I’m going to say something controversial so make sure you’re sitting down. I do not think jeans should be considered sportswear. I think of sportswear as having the air of being quite dressed, and to me, that means no denim. As old fashioned as that sounds. But I consider this is actually a blessing in disguise. Because look how much more dynamic this outfit looks with white chinos!!!

Our Maria McManus velvet blouse is the perfect topper for these crisp, cotton Tory Burch chinos (I had to hem them like 8 inches, no joke, so don’t freak out when they arrive :)). You could also try a Yali velvet jacket if you wanted more color. OOOO or what about something really decadent from Colleen Allen…if you’re NOT coming from the office.

Sure you could wear a red fringed halter top with jeans. But with white chinos, it’s a whole look!

A black blazer office-ifys (making up new words everyday here!) this red fringy halter top (if your size is gone I love this green Sea fringe top. Or this red crochet Heirlome. OOOrrrrr for more coverage, this from Ashlyn!), white chinos and pointy pumps.

Blazer comes off for a real party! Tory Burch’s fish necklace (to be discussed further below) adds another kooky element to take the pressure off the very statement-y halter.

Same same but different. Red jacket, white pants. A little razzle dazzle. It would be hard to wear a fully sequined jacket/cardigan/thingy all day with a black skirt or jeans. Just too statement-y. But with white chinos, it’s casual! I’ll rest my case now.

Add something winky

Sportswear evolves with the decades, as I said earlier. It obviously meant something different to Halston than it did to Ms. McCardell. Today’s sportswear takes elements from these eras and is loosening them up even further and mashing them together. In the end, it’s all comfortable, just a new way of using standard elements like a polo, a straight skirt, a cotton dress. Proportions are a bit more extreme now. Huge shoulders. Sheer skirts. Layered knits. Pooling hems. But if you stick with the classic general categories, you can weave in some of these elements successfully. And then…add something cheeky like a fun belt. A statement necklace. An animal printed shoe to bring it all back to that whole confident lady look we are going for.

SANTA!! But make it business casual. 🤣 My red wool trousers and a black sweater can pass for holiday dressing with a North Pole themed belt. LOL! Our Versace belt lives on. This Tory black belt/gold buckle is so great too if the Versace is too too for you. (Shoes are also Tory.)

An “indoor leather jacket” is good for something like this. As is a any black blazer or shorter wool coat really. Anyone else dying over this? Should we vintage Armani it?

I can’t wait to wear this outfit to a weeknight holiday party coming up. It has all the classic elements that I love: a striped polo or cardi, a knee length skirt – Leset slip skirt under my sheer!), a weird shoe, a braided belt. The worky bag and the “diamond” jewelry (Dorsey neckace, Bauble Bar earrings for the holiday WIN!) tie it all up in a nice, ladylike bow.

And then of course, everything looks better with this coat over it.

Speaking of shiny tops (yes that yellow striped top above is sparkly), there might not be a more straightforward way to scream holiday party than a top with a little shine. The trick of course, is to make these tops work for your workday. I love this mermaid blouse from Margiela (below) which I layered with a black silk cami underneath and threw a leather jacket over to tone it down.

A recurring theme that I’m realizing as I write this is that brown helps temper fancy clothes for daytime. So a brown leather jacket instead of a black one. A brown belt to break up the sparkly top (alts here and here!) and the shiny pants. You get it.

You could also swap your leather for a black blazer which might be easier to keep on indoors during the day. If you do so, though, keep the brown belt and maybe swap this black heel for a brown one to keep that brown theme going?

This is the vibe, no?!!?!

Tie closures – an American Sportswear micro-trend

Tie closures cannot actually be credited to American sportswear. Heck, they can be traced to people dressing themselves from the beginning of well…documented history. But something about an asymmetrical tie feels very of the American sportswear golden age to me. A little retro. A little louche when undone, communicating a relaxed feel. And a simple extra flair when all the way done up, conservative but not boring. This sweater easily does the trick. As does this dress which I ordered already lest you all gobble them all up. And finally so does the “housecoat below.” Fun over a black skirt or with our pastel pants!

And in the spirit of our fashion forefathers (mothers) this dressy take on a housecoat, complete with asymmetrical ties worn on top of our pastel trousers! Who said your office was in midtown after all!? Tory bag and shoes.

And if all else fails!!! Nothing quite like a your favorite black power dress with cheeky accessories to start a conversation at the bar.

This is an office to party newsletter after all. So I would not leave you high and dry without dreamy black work dresses. From left: Rus, which has those “sportswear” ties that I love, Prada nylon in a perfect shape, though I’d definitely replace the belt with something non-logo’ed like this, Me + Em black tweed – hem to the knee!, The Row on final sale, but totally worth the risk IMO, Emilia Wickstead’s black/white tweed. Yes, I know it’s not black but it does the same thing and it’s just GORGEOUS no!? This Givenchy is incredible. Most powerful woman in the room energy (though you might need to tack that slit slightly.) And the Cos at right is most similarly shaped to the Bally I’m wearing below that is no longer shoppable sadly.

My favorite old LBD from Bally. I wear this dress infrequently, but when I need it, I NEED it. So this is your call to action to procure the best LBD your budget can take and keep it in reserve. Tory shoes and necklace. Do you think their FW26 accessories were inspired by my anchovy newsletter!?! And my dream pouch by Sophie Buhai.

I could keep going, but then what would we talk about next week??? Happy schedule to the MAX season! See you back here next Sunday.

Yours TRULY,

Becky

5 Things You Should Buy is my favorite way to make your day easier. Please consider upgrading to paid to support this work so I can keep bringing it to you every Sunday. I love you!

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