How I'm Packing for 36 Hours In New York
3 days of work meetings, 2 travel outfits, and 1 cocktail look in a single carry-on bag! Will I freeze my face off? Perhaps.
Greetings from me, in frantic packing mode! I’m spending my Saturday (surprise, I write this newsletter basically minutes before I hit send) packing for an incredibly quick trip to New York. I have essentially 36 hours in Manhattan, and a bonkers schedule of client meetings, seeing my Marie Claire and Who What Wear teams, plus a work dinner event, which requires cocktail attire. As always, I refuse to check bags 99 times out of 100, and this trip will be no exception. The part that’s tricky is the whole winter travel of it all—requiring bigger/heavier items, obviously—plus the cocktail attire piece. And of course, I don’t want to look like a dirtbag, so there’s that.
While I would love to say I’m so good at this, and just throw random things into a suitcase and dash off to the airport, that isn’t my reality. I’m pretty annoying about how I plan, but while it feels like a heavy lift up front, it usually makes the trip itself less stressful, which is always a good thing.
When planning, I naturally start by cataloguing all of the events that will require outfits.
Monday: Travel outfit + work dinner/drinks outfit + cozy outfit for hotel work/sleep.
Tuesday: Daytime work outfit + cocktail attire outfit + cozy outfit
Wednesday: Daytime work outfit + travel outfit
Next I look at the weather, which seems dreadfully cold, though probably moderate for anyone who doesn’t live in Southern California. The forecast means I need to bring serious outerwear, so I’m going to pick one larger coat that I can wear on the plane and that will work with all of these looks. In a perfect world, I would have a travel coat and a coat for the trip itself, but I’m trying to be less of a diva about that.
My centerpiece coat is an olive green, floor length, alpaca wool Brandon Maxwell coat that I bought on a crazy sale over a year ago, and am just getting to wear this winter. It’s double breasted, slightly oversized, and as cozy as can be. Sadly it’s sold out, but if you’d like a similar style that’s a bit shorter, Kassl Editions makes a cool option and Khaite has a more bathrobe-y style in a similar hue. Since everything I pack needs to work with this coat, I’ve decided to stick with a palette of black, navy, burgundy, and gray for the rest of my wardrobe.
Quick aside to say I’m currently testing Dr. Diamond’s Metacine Instafacial Infusion Biometric Microcollagen Matrix Serum ($325), which is no doubt going to be as good as the brand’s Plasma, which I swear by, unfortunately. Friends, I never want to like expensive skincare, but so far, I’m optimistic. You use the new Infusion morning and night on slightly damp skin, after using the Plasma, and the airy gel serum contains three types of microcollagen peptides to improve elasticity. It’s early days, but I’m into it! Now back to our regularly scheduled programming
MONDAY
Travel: My flight is at the crash of dawn, and I’m wearing the closest thing I can to fancy pajamas: A pair of satiny J.Crew pull-on pants (which are on sale right now!), a super soft Negative Whipped Long Sleeve T-Shirt ($110), which will be the theme of this trip, I have…a lot of them, a black oversized men’s cotton rollneck sweater, and my cozy Jamie Haller leopard loafers.
Work Dinner: Thankfully, this is a casual dinner with a longtime friend in the industry, so I can basically just drop my bag, change my shoes and my sweater, and go. However, I rarely do that, and have an outfit planned in case. The base is the Tibi Dominic Pinstripe Long Trouser Skirt ($525), which looks good styled lower on the hips and without a belt, or sometimes I like to smarten it up with a simple belt like J.Crew’s Double Buckle Belt in Italian Leather ($52.50 on sale now), a slouchy black cashmere sweater, and Jamie Haller The Kitty Points (aka “Bitchy Low Heels” ($595) in Maroon Suede. The color palette abides!
Cozies: My cozies are the same for Monday and Tuesday: The New Yorker x J.Crew Relaxed Hoodie ($128), which I bought the second the collab was announced, and is perfect, and my beloved The Great The Jersey Crop Pants ($145).
TUESDAY
Daytime Meetings: When I’m in New York for a short period of time, I’m rarely in the office, as it’s usually more important to meet with our commercial partners to discuss about upcoming campaigns, new editorial programs and tentpoles, and connect the business and creative sides of my work. Tuesday I have meeting all over the city, so I’m keeping it simple with my beloved Callas Milano Luca Sailor Pants ($690), which are interesting, polished, and don’t wrinkle, styled with a super soft Negative Whipped Long Sleeve T-Shirt ($110), J.Crew Cashmere Classic-Fit Crewneck Sweater ($148), and Jamie Haller The Kitty Points (aka “Bitchy Low Heels” ($595) in Maroon Suede, plus the Brandon Maxwell coat and Coach Brooklyn 39 Bag ($495), which is the perfect work bag and fits my laptop.
Evening Event: I have a work dinner that’s cocktail attire, and thankfully have time to stop at my hotel to change. I’m packing two skirts, just in case, as I sometimes like to have an option in these situations. Since I don’t feel like going all out for color, I’m going to bring interest to my outfit with texture, specifically: Sequins. Packing a Brandon Maxwell black sequinned midi skirt with a zipper I bought via the sample sale last year. (My skirt is sold out, but La Ligne makes a black midi sequin skirt that’s on the more affordable side, and 16Arlington has one with larger paillettes that’s also cool.) I’m going to style it with a slimmer cashmere sweater, like Co’s long-sleeve crewneck, which tucks in nicely, or a slightly thicker one from J.Crew if it’s really cold. For the classic-fit cashmere, I size down, and wear an extra small. Heels are my favorite workhorse shoe, Gianvito Rossi’s 70mm Suede Pumps ($795), which I’ve had for a thousand years and have worn ten thousand times. They’re timeless, comfortable, and elegant, and I can wear them literally all day long. My bag is a little black velvet Doen bag that is part of the Doen x RMS Soiree Set ($128) and also comes with the most amazing products, so is definitely a must buy.
WEDNESDAY
Daytime Meetings: Is it wild that I’m planning on wearing a skirt without boots or tights? Sure, but most of my meetings are close to my hotel, and I don’t have to walk very far. So I’m packing my favorite black leather midi skirt from Ulla Johnson (if you read this newsletter regularly, you know I bought it by accident on my last trip to New York). As you might have guessed, my exact skirt is sold out, but Madewell has a leather midi skirt that’s quite similar on sale now, and Frame makes one in croc-effect leather that is dreamy. Same as yesterday, I’m layering with a super soft Negative Whipped Long Sleeve T-Shirt ($110) and my brand new, limited-edition The New Yorker x J.Crew Cashmere Crewneck Sweater ($168) in an extra small and the same Jamie Haller The Kitty Points (aka “Bitchy Low Heels” ($595) in Maroon Suede. Also wearing my go-to Khaite jean jacket, which I am somehow not sick of, though I’m sure you are by now. The Brandon Maxwell coat is big enough to go over the whole look, which is great!
Travel: The best part of my daytime outfit is that it easily transforms into something that works for travel. I’m heading straight to the airport from my meetings, but will stop to change out of my skirt and into some cozier pants. Lately, I have been hyper fixated on a newer pair of pants which are Jamie Haller’s The Big Pleat Trousers ($598) in Black. They’re so slouchy and soft and comfortable, but still elevated! I have worn them four of the last seven or eight days; that’s how much I love them.
I’m wearing them with another new-to-me piece that is hyper versatile and excellent for everything from school pickup to travel: The Only Jane The Josie Jacket ($350), which is so dang good. I have it in a medium, because I wanted it to be a smidge oversized, and it is the nicest Italian denim I think I have ever felt. And it has an excellent amount of pockets! My friend Jane makes the line—we met as assistants at ELLE back in the early aughts, and I have now known her half my life!—and she is insanely thoughtful and intentional with every product she makes. Very much recommend checking out her line, and this jacket in particular is a revelation.
Okay friends, that’s it for now. If you want to follow me on @hillarykerr, I’d love it. And if you have anything to say or ask (preferably nothing terribly mean), please drop me a note either via DM or in the comments below.
As always, thank you for taking the time to read this post. I’m truly so glad you’re here. If you like what you’re reading, please consider sharing this newsletter. (And if you have the time to like it, that would mean a lot to me!) All products mentioned are independently chosen, and some may be affiliate links. Your support is appreciated.
Hi Hillary! Do you have suggestions/have you written a newsletter before about office dressing? I am starting a new job in a law office that is ‘business casual’ (what is that even?!) but will sometimes require suits for client meetings. I’m basically starting from 0. My schedule is hybrid, so I’ll be dressing for 3 days in office. What are some key pieces you would suggest in investing in to start a work capsule wardrobe? THANK YOU SO MUCH I LOVE YOUR NEWSLETTER 🫶
I wish I hadn’t learned about the frame croc leather skirt… now to wait for a sale! Or just save up. As always thank you for the inspiration with all the outfits.