Everything I Packed For A 3-Day Work Trip To New York, Including My Mistakes
72 Hours, 12 Meetings, 2 Planes + 1 Event
As per usual, greetings from 30,000 feet! Currently en route back from a quick work trip to New York and the in-flight wifi is spotty, which means I’m writing this newsletter slightly ahead of time, and not at 9 p.m. on a Friday night.
After a handful of years when I didn’t travel tons for work—apparently when one accidentally has one’s first baby approximately 2700 miles from home, it dampens the desire to get on a plane?—my job now requires more work trips, and I’m still figuring out how to pack for them. Prior to having kids and pre-pandemic, I was always on a plane, and had the art down to what felt like a science. It’s crazy how quickly that skill gets rusty though, and it certainly doesn’t help that my “before times” uniform for both work and travel has also changed. Ah, the joy of having an ever-evolving body, career, and personal style.
But no complaints—really!—because I feel like I’m starting to nail what I need to pack, and correctly ascertain what I can leave home. And I thought I’d share the highs and lows of this latest trip, so that hopefully it can help you pack more wisely too?
The Trip: LA → NY → LA
The Requirements: 3 days of proper meeting outfits, 2 travel outfits, 1 casual meeting outfit, and 1 event look
The Constraints: Must fit into 1 carry-on bag and 1 piece of personal luggage. I wrote about my go-to bags last October, and stand by that reporting.
Travel Outfits: As I’ve mentioned recently, thanks to Marie Claire’s amazing editor-in-chief, Nikki Ogunnaike, and her phenomenal newsletter Self-Checkout (which has over 100k subscribers just a few months after she launched it and is free; you should sign up!) I am now obsessed with “hard pants” for travel. Except they’re the softest pants you can imagine.
So how did that happen? Well, Nikki’s a fan of Nili Lotan’s Shon Pants ($375), which I bought and love love love. I’ve written about them before, and will continue to because they’re that damn good. So soft, so comfy, so relaxed. Again, I’m 5’5” and didn’t size down because I wanted them extra slouchy; if you want them more modestly slouchy, go down one or two sizes.
A lightweight jacket with lots of pockets is key for travel for me, so I took my new, really soft, really lovely J.Crew Denim Barn Jacket ($168), which sadly isn’t a part of the 30% off sale on new items, but still a very good price for a very well-made piece. Mine is a small (again, I didn’t size down because I wanted the slouch for layering and just the overall look), and yes, I know I have an admittedly bonkers number of denim jackets, but this one is very practical for travel because it has four pockets and a super soft collar.
As per usual, my t-shirt is The Great’s The Slim Tee ($95), which is the best t-shirt on the market IMHO, and the shoes are my always standard black chucks. I packed an extra t-shirt for the trip home, and a relaxed sweatshirt that I wore as a scarf-slash-pillow.
Proper Meetings: Trips to New York usually fall into one of three buckets, with some overlap. Sometimes I’m there for strictly editorial purposes, and go to fashion shows or events, other times I’m there for internal strategy meetings with my boss, colleagues, and/or the executive leadership team, and then some trips (like this one) are primarily focused on meetings with our advertising partners. Don’t tell anyone, but the latter is usually my favorite kind of trip, because I really enjoy talking to the phenomenal people who run the world’s most important brands. It’s a complete rush. Plus, I get to share all of the exciting things that I’m doing with my amazing editorial teams, and ideate on ways that we can work together, a combination that delights my brain to no end.
Since I have limited space in my suitcase, I usually stick to a black-and-white color palette for these trips, and try to bring no more than two pairs of work shoes. I also try to only wear pieces that I’ve worn before, because there’s nothing worse than breaking in an uncomfortable pair of heels when you’re trying to be on your A-game. Or wearing a skirt that looks great when you’re standing, but attempts to ride up to your collarbone when you sit down. Or spend 20 minutes steaming a new dress, only to have it turn into a wrinkled, impotent mess the second you step out into Manhattan humidity.
I packed three main looks for these meetings, and then broke most of my rules because I also did a last-minute, same-day delivery shopping session at Net-A-Porter on the plane.
The final outfits were as follows.
Day 1: Black-and-white polka dot silk skirt from Tove (also comes in gold, and is on sale in red or black), a black puff-sleeve cardi from Doen, that’s also available in gray or burgundy (it’s short sleeved, which is perfect for transitional weather), my trusty Khaite oversized denim jacket, and my most comfortable Dior kitten heels, which I REGRET TO TELL YOU now come in leopard, ugh so cute, and leather, which I feel will be even more comfortable?!? (Also, there are lots of options on The RealReal, if you’re so inclined.)
Day 2: This was not the plan. I brought a long sleeve black silk Zimmermann dress that has kind of a witchy shoulder for this day, but in my aforementioned Net-A-Porter shopping panic (more on that) I bought an incredible Ulla Johnson paneled leather midi skirt, and ended up wearing that with a James Perse classic v-neck t-shirt, which reminded me anew that it’s just a really great brand. Shoes are older Jimmy Choos, specifically the 65mm Fetto, which is a d’orsay slingback and I think the best shoe in the world maybe? I dream every day that the brand will bring this exact style back. Until then, JC makes a shorter style that I also have and like, but a girl will still dream. Side note: I think J.Crew’s faux leather seamed circle skirt has really great vibes too, and would have packed it, but it didn’t arrive in time! And that’s on me.
Day 3: As I’ve mentioned before, I can’t really walk away from a fitted black midi skirt with some sort of dramatic detail, and this season it’s Shushu/Tong’s draped wool and silk skirt, which is beautifully done. Since the skirt is a bit of a statement IRL (it reads quieter in photos), I let it hog the spotlight and just wore a simple black wool sweater on top, like Gap’s merino wool sweater, which is currently on sale! Technically I’m wearing an old J.Crew Tippi sweater here, but it’s no longer available and I thought I’d grabbed the Gap one, hence the link.
Casual Meeting: Did I need to pack for casual meetings? No way, but they tend to pop up unexpectedly, so I always throw in a couple of easy things for last-minute moments. For me, that meant packing my new favorite Doen dress style, the Rhodia, which is super lightweight, but fun to wear, and I already own another version. And yes, I know it’s funny that I buy multiples, but for $248 it’s absolutely worth it to me, as I feel like the best version of myself in it. Also brought my great, incredibly soft Jamie Haller black loafers, which are also on Shopbop now!
Note: I wouldn’t say it was a total mistake to pack these pieces, but I did not wear the shoes and didn’t need to bring them. Sneakers and two pairs of work heels that are walkable was truly enough; I should have skipped the loafers. In retrospect, knowing I was going to buy shoes for the event (see below), I would have definitely not brought the loafers, as I always end up shopping a little in New York, and I absolutely should know that about myself by now.
Event: One of the other major reasons I went to New York was to celebrate Marie Claire’s 30th anniversary, which we did in collaboration with Bloomingdale’s From Italy With Love amazing collection. For the event, I wore a silk top and maxi skirt by La DoubleJ, and a last-minute purchase (do as I say, not as I do!): Gianvito Rossi slingback sandals.
While buying party shoes at the last second is literally a terrible idea, I will say that I was pleasantly surprised by how comfortable this style was, and I hope they make it in suede or non-patent leather, as I would totally buy another color. They have a 55mm heel, which I’m now realizing is in the range of my ideal heel height. (In a perfect world, all shoes would have 65mm heels, which makes me laugh even to type, as I wouldn’t leave the house in under 100mm when I was in my 20s and most of my 30s. My, how the times do change.)
Before I sign off, a question for you: Do you have a go-to outfit for work travel? Mine is always evolving. For a long time, it was a stretchy black cropped jean and an oversized striped shirt, usually with a camo utility jacket, though last year with a slouchy camel A.L.C. coat, always. I also used to wear a stretchy black maxi slip dress with non-itchy Commando opaque tights, plus moto boots and an oversized vintage concert t-shirt. For overnight flights, I like a soft Anine Bing t-shirt and Vuori joggers, plus a soft double-breasted coat. Anyway, if you have a combo that you really like, let me know. I’m always interested in your ideas!
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.
This may be too specific, but I too LOVE a midi skirt and would love a roundup of some of your favorite styles at different price points!
I love reading your recommendations but they’re aspirational for me other than the jcrew recs! Here’s my lower budget version - I’ve been wearing Vince platform sneakers as my work travel shoes; they’re comfortable but I feel like the platform is slimming (could be making that up) and they can be dressed up or down. I’ll usually wear with a pair of black jeans (Levi’s ribcage, frame le Jane crop, Hudson Barbara - I know skinny isn’t in but idc because the stretch of this pair is so nice for travel) or the anthro collete wide-leg cropped pants and a nice tshirt and then a sweater, jacket, blazer, or sweater-jacket hybrid. I typically bring a tote in my carry on and use the everlane renew transit backpack which I love; I just can’t get behind a personal item bag that doesn’t zip! I use a Ganni nylon leopard crossbody for my essentials and then stuff it into my backpack before boarding.