Everything I Wore On A 72-Hour New York Trip (+Two Extra Outfits), Which All Fit In My Insane Carry-On Bag.
It was a HOT 61 not a COLD 61 and honestly all the weather apps lied to me.
Hi everyone, and happy Mother’s Day, if that’s your thing! (Especially HMD to my mom!) I’m in a mild haze after another whirlwind 72-hour work trip, but want to start by thanking everyone who reached out after I wrote about my kids having a hard time with my recent uptick in work travel. Thanks to tips from you all, I tried some new tricks, including telling them approximately 24 hours ahead of the trip, but not before a separation like bedtime or leaving for school. They knew it was happening soon, but didn’t have too much time to ruminate. Also, my husband made them a chart to color in the days to understand when I would be back, and that seemed to be helpful. My daughter really doesn’t love it when I’m gone, and these two things seemed to help.
A few years ago, I had the pleasure of interviewing fashion and beauty exec Daria Burke for Second Life, and fell in love. Her career is fascinating—she worked for major brands like L’Oreal, Estee Lauder, and Rent The Runway, and led fashion and beauty partnerships at Facebook before working as JustFab’s CMO—and she’s just so funny, kind, and brilliant. So when she wrote her memoir, Of My Own Making, I was excited to read it, and then floored by her personal story of triumph over trauma, and how she shaped her life’s journey.
Needless to say, I’m honored to share that I’m interviewing Daria at Godmothers in Montecito on Thursday, May 22nd at 6 p.m. and hope to see some of you there! If you’re in the Santa Barbara (or adjacent) area and can join us, please RSVP via Godmothers, as this is a ticketed event. All details are on the store’s website, and I’m linking here. Trust me when I say that Daria is truly a phenomenal individual, and deserves all of our support.
And now, with no further ado, let’s get into the story that resulted in more astonished DMs than anything I’ve posted as of late: My recent packing job!
As I’ve written about extensively, my hand luggage is more utilitarian than aesthetic, and I’ve had my main carry-on bag for over 17 years. It still looks brand new and fits a shocking amount of stuff, which you all noticed. So every trip starts with a Briggs & Riley Baseline Essential 22-Inch Expandable 2-Wheel Carry-On Bag ($659).
Also, ahead of arriving at the hotel, I request a rolling rack and a handheld steamer in my room. The second I get in, I immediately unpack all my clothes, hang them up, and steam them. I’m not saying you should do this or that this is normal; I’m saying this is my weird process. And when I posted a photo of just that, everyone lost their minds. Specifically wondering: How could I have possibly gotten so much stuff in one bag? Well let’s break it down.
The Schedule: Early Tuesday departure, dinner with a friend that night, meetings with our advertisers all day Wednesday, Marie Claire’s first ever Power Moms dinner that night, meetings with clients all day Thursday, hosting a styling and shopping event with the incredible stylist and consultant Tiffany Reid at Emporio Armani on Thursday night, and then early flight back on Friday morning.
The Packing: This schedule meant I needed two travel outfits, two event outfits, two daytime meeting outfits, and one dinner outfit. Plus casual clothes for working in my room and having hair and makeup done. Essentially eight or nine looks, total, plus one backup event look and one backup daytime look. So realistically I was packing approximately 10 to 12 looks. Oh wait, I forgot; I was kindly given an Emporio Armani look for the event, and that was waiting at my hotel, so let’s call it 10 looks even.
Day One: Travel + Dinner
I didn’t take pictures of my travel look, because it consisted of pieces I often wear: Nili Lotan Shon Pants ($375) in Carbon, which are absolutely incredible and a trick I picked up from Marie Claire’s editor-in-chief Nikki Ogunnaike. They are so soft, they feel like pajama pants, but are tailored enough that you look polished. They run on the shorter side; I’m 5’5” and wear a size 6, and didn’t have to have them tailored.
Surprise surprise I wore them with a Negative Whipped Long Sleeve T-Shirt ($110) in medium/black, which I had slept in the night before, a J.Crew oversized Cashmere Sweater ($188) in medium/black, and my trusty Jamie Haller leopard loafers, which have sold out since I last wrote about them, but often come back if you sign up for the waitlist. Plus my go-to oversized camel A.L.C. coat (which I found on The RealReal for less than $250!) that is a comfort blanket for me at this point. Very standard look.
My dinner date ditched me for a last-minute work obligation, and I got in 1.5 hours after I was meant to, from a flight into JFK that was so bumpy the fasten seatbelt sign was on the entire trip, which meant I was exhausted. So I ordered a kale salad and the chicken kabob with peri peri sauce from Jack’s Wife Freda, and started watching the new Tina Fey/Steve Carell/Colman Domingo show The Four Seasons on Netflix and honestly, it was a dream evening. I wore The Great’s The Jersey Crop Pants ($145), which I have in most colors and sizes, it really doesn’t matter they’re all great, because these are the best lounge pants on earth, and I will keep shouting that until the day Emily and Meritt stop making them. May that never happen.
Day Two: Meetings + Marie Claire Power Moms
When I’m traveling for work, I’m usually in meetings with my incredible colleagues who work on the sales side of our business, and we call on our partners to talk about what they’re working on, upcoming launches and initiatives, and then also what we are working on from an editorial perspective. I love these meetings because I end up walking away with a thousand new ideas about stories and opportunities we can create, but also because I get to celebrate the phenomenal work that our editorial teams are doing.
As per usual, I had a whole look planned for this day—a mid-calf colorful print Marni skirt I bought a decade ago with a simple sweater—but the forecast was highs of 61, which made me think I was going to be cold. Tricked again! But with that in mind, I wore my trusty black leather Ulla Johnson skirt, a now vintage J.Crew Tippi sweater in black, Dior slingbacks, my A.L.C. coat, and my standard Valentino bag, which I also brought to London with me.
For the Marie Claire Power Moms event that night, I was deciding between a floral silk Marni Dress ($1795) and a black silk and linen Zimmerman dress that I’d purchased a number of years ago, but had never really had a spotlight moment. (There are some versions of my dress on Poshmark and eBay, and this shorter version too; I take a 1 or 2.) I was worried I’d wrinkle the Marni one too much before the event, so I ended up wearing the Zimmerman dress with an older pair of black suede Paul Andrew mules (sold out, but the Staud Brigitte Suede Mules ($295) are similar at a better price point) and a Cartier clutch that is no longer available. So again, yes, I often wear expensive things, but I wear them for literally decades!
Also, I just have to say, the event was truly a delight on every level. Along with Moms First, we celebrated Marie Claire’s first ever Power Moms list, including Gabrielle Union, Kali Uchis, Deepika Padukone, Bobbie founders Laura Modi and Sarah Hardy, Cherelle Griner, and J.Crew’s Olympia Gayot.
Day Three: Meetings + Emporio Armani Event
I had exactly one martini at the event, which is all I needed, as I had amazing seatmates including my dear friends Dr. Shereene Idris (you know I am obsessed with her skincare), the founder and CEO of Argent, Sali Christeson, who is my Virgo sister, and fine jewelry designer Stephanie Gottlieb, who was wearing the most divine martini olive ring I have ever seen. (And since the olives are made from peridots, which is my birthstone, I feel like I need it, no?)
But while I was moderate in my drinking, I was pretty tired the next day and had a breakfast meeting, so decided to let a colorful sweater perk me up. I wore a gray J.Crew Cashmere Shrunken Crewneck Sweater ($148), my gray accordion pleated Jamie Haller skirt (sold on on her site, but I found one here), my beloved Guest In Residence Shrunken Pointelle Crew Sweater ($265) in Lemon in a medium, and my go-to Dior heels. Again, as I mentioned in my London packing story, this sweater is 10000% perfect; so soft, light, and airy, it’s crazy. This outfit made a lot more sense for the weather!
That night, I hosted a shopping event, and got to pick out a look for the evening. I chose an Emporio Armani Midi Skirt with Rouging Motif ($495) which is so insanely comfortable and can be easily dressed up for cocktails, but will also look great with loafers or sandals and a t-shirt this summer. For the event, I paired it with the brand’s Linen-Blend Blazer with Belt ($1195) and the unbelievably comfortable Satin T-Bar Sandals with Rhinestones ($695) that I cannot recommend enough. Insanely elegant on the foot, with a surprisingly roomy toe box, so you can stand in them for hours (l literally did) and your feel will feel grand. I didn’t know the brand’s shoes were so good, but now I do!
In addition to getting to co-host with the incredible stylist and consultant Tiffany Reid, it was such a pleasure getting to meet so many Who What Wear readers, many of whom also read this newsletter! I never get tired of hearing that, and was so touched to hear these stories. I was also knocked over with delight to see one of my former colleagues, Faith Xue, who is the new editor-in-chief of The Coveteur. Faith led our former beauty brand, Byrdie, and I loved every moment of working with her. We’ve stayed in touch, and I was thrilled to see her rise to become the executive beauty director of Bustle Digital Group before taking her current role. Faith is one of the best humans in the business, and I think you can tell how thrilled Tiffany and I are to see her. I hope to work with both of them again soon!
Day Four: Travel Day
You’re never going to guess this, but I wore the same thing back to LA that I normally do: J.Crew Stratus Pants in Textured Satin ($89.50) in medium/black, plus a Negative Whipped Long Sleeve T-Shirt ($110) in medium/black, which I had slept in the night before, a J.Crew oversized Cashmere Sweater ($188) in medium/black, and my trusty Jamie Haller leopard loafers. I LIKE ROUTINE, PEOPLE. It makes me feel safer in situations where I’m not in control, like flying.
As for the packing itself, I do use packing cubes from Paravel—(the Packing Cube Quad ($70), to be exact—but I also have some really inexpensive ones from Target that work fine enough for me, too. One note: I have darker cubes and more colorful ones, and I think the colorful route is the way to go, otherwise they get visually lost in your bag. I also have different colors for me and each kid, so that I can just glance at the cube and know to whom it belongs. Personally, I just take one packing cube and use it for my undies, sleep shirts, and bras.
Otherwise, I don’t have a ton of tricks for getting all this stuff in my bag, other than I try to be very strict about the number of shoes and bags. If you were keeping count, I wore one pair of shoes on the plane, and packed two others; the Emporio Armani ones were at my hotel, and I ended up mailing that whole look to myself because I couldn’t add it to my suitcase. So I guess that’s a diva trick. Also, I brought one bag in my personal item, and then packed the evening clutch, which is very flat. Sweaters and cotton items get folded up and back first, along with shoes, and the cube of undies.
The rest of my clothes I literally just fold in half and lay on top of all the sturdier stuff. My main carry-on bag is really pushing the limit of what you can take, and I’ve mentioned before that when flying domestic and connecting, it sometimes is too big and a hypervigilant staffer has insisted I check it before, so that’s a risk, but I haven’t had too many problems on LAX to JFK or LHR, which is my main route. I’m going to Atlanta next week for Marie Claire’s Power Play event, so will try a smaller carry-on bag and see how that goes!
Oh, and my last trick is that Net-A-Porter has multiple categories of same-day delivery when you’re in New York, so I always remind myself that if I forget something, I can literally have options to my hotel in hours. In fact, I bought a Zimmermann Crush Striped Stretch-Knit Top ($495) and matching Striped Stretch Knit Midi Skirt ($525) from the app after boarding my flight to JFK, and it was waiting in my hotel room when I checked in. Yes, I am ridiculous.
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.
I look forward to reading your posts every Sunday!!! So friendly, approachable and still fashion!! I love that you don’t gate keep things and celebrate the people/brands you love. It’s a slice of joy!!!
I think we need to see How you pack the bag. lol.