Packing for London Broke My Brain. Here's What I Won't Do Again, And Also What I Got Right.
Yes, I had a meltdown over a three-day trip. Hopefully I am not the only one who has had this experience.
Last Sunday, I had a full-on sweaty meltdown in my closet, trying to pack for this trip that was so bad, I texted my friend Rory and begged her to meet me for an emergency walk. I can’t remember the last time I was that dysregulated and frustrated, and felt like such a fraud. How could I, the founder of a fashion website and writer of this email, be so thrown by packing for what is ultimately a low-stakes work trip?
Turns out I set myself up for dramatics by ignoring my normal rules for packing. And yes, I know it’s odd that I need rules for packing, but we cope how we cope! Also, on my endorphin-boosting walk, my friend reminded me of the universality of my closet meltdown. “If you haven’t stood in a closet full of perfectly good clothes, freaking out because you feel like you have nothing to wear and that nothing fits, you might not be human,” she said. “It’s peak girlhood.” Honestly, I’m glad she said because it snapped me out of my spiral.
So where did I go wrong to start?
First: My closet and bedroom were already messy to start, and messy room = messy feelings, at least for me. We had family in town (both my husband’s and mine) for Easter, which we vaguely celebrate—meaning: yes to egg hunts and baskets for the kids—and while I love hosting, I was behind in laundry and general organization. So my bedroom was just piles of clean clothes I hadn’t put away (I reasoned that I was going to pack lots of them, so what’s the point), and my closet looked like I’d taken an eggbeater to it.
Because things were messy, I couldn’t find my go-to travel skirt, a black below-the-knee pencil skirt with a big bow on it, which I’d bought in London over a decade ago from the brand Roksanda. I always reach for this skirt for work trips because it looks cool and polished, never wrinkles, and makes me feel like a boss.
Instead of just methodically looking for it, I then decided that what my closet really needed was a proper organization, and that I should go through all of my skirts and separate them into categories (donate, store, and keep). Then for the skirts I thought I might take, I decided to try them all on, which resulted in another mini storm, as a couple of the pieces I thought I might take didn’t fit the way I wanted. Like Goldilocks, some were too big and some were too small, and I could feel my frustration rising. My body fluctuates, which I have made semi-peace with, but as each outfit I’d already constructed in my mind—yes, I plan in my head before actually packing—fell apart, so did I.
To make it even worse, I could hear my kids playing outside and having a wonderful time with my husband, mother-in-law, and sister-in-law, while I was stuck inside confronting my own style failings. I realize this is absolutely mad on my part, because obviously I was happy they were all having fun and I’m so lucky everyone gets along so well, but the childish, bratty part of me felt lonely and left out because my lizard brain is apparently a petulant and selfish teen.
On top of all of that, I’d had such wildly varying advice on what level of cold to expect in London, which also was frustrating, as I could only pack one coat for the trip, since I’m a die-hard carry-on traveler, especially for work. Again, I just want to acknowledge how silly I was being. I was packing for a work trip that was 100% internal meetings. I didn’t have any events, my colleagues don’t work in fashion and probably wouldn’t have noticed if I’d turned up in a paper bag, so all of this stress was self-inflicted. I am truly my own worst enemy sometimes. And the reason I’m telling you all of this is because I’m embarrassed that something so minor sent me into such a tizzy. But I also think it’s important to acknowledge my own difficulties, in the hopes that it makes one person feel less alone. Or maybe it will just make you laugh at me, and honestly I’m fine with that too.
Oh and to close things out: I did find the hero skirt. It was on the last hanger I went through at the very end of my organization process. And I didn’t even end up wearing it. Of course.
PS: One more question. If you have kids, how do you discuss travel with them? My youngest gets really sad when I travel, and I have tried a bunch of ways of letting her know about an upcoming work trip, and haven’t had any success. When I tell her ahead of time, she gets quite worked up about it, when I tell her right before I go, it doesn’t go over well, and when I ghost her and leave it to my husband to explain, that seems mean to everyone. When I got home from London, she asked me not to travel for work anymore, and I don’t have the heart to tell her that I’ve got another work trip to New York coming up in early May. It breaks my heart, and I can’t figure out how to get the information out in the least painful way. Any advice would be appreciated.
WHAT I PACKED + WHY
Travel: I didn’t take a photo of it because I was fussed and rushed (it’s like booked and busy, but less glam), but I stuck to my current travel uniform of J.Crew’s Stratus Pants in Textured Satin ($89.50 on sale now, normally $148) in black/medium, the world’s hardest working piece a.k.a. Negative’s Whipped Long Sleeve Shirt ($110) in black/medium, J.Crew’s Relaxed Cashmere Crewneck Sweater ($188) in black/medium (sensing a theme here?), Jamie Haller Leopard Loafers ($455 on sale now, normally $650) in a 38, and my vintage black and white herringbone Burberry coat that I wrote about for another London trip in 2022. I packed an identical set of trousers, shirt, and sweater for the flight home because if it ain’t broke, why fix it?
Office Day 1: I landed at LHR at 11 a.m. and had meetings starting at 12:30 p.m., which meant not a lot of time to get to my hotel, drop my bag, change my clothes, and walk to my office. In my head, I’d planned on wearing my aforementioned black Roksanda skirt with a bow—which I can’t find online anymore, but I did spy a light olive iteration on eBay that I’m seriously contemplating!—but because I had planned to have a couple of walking meetings, realized that skirt is better suited to sitting, and changed everything up.
Instead, I wore my other favorite travel piece: A long-sleeve silk floral Rodarte dress that weirdly never wrinkles. I found one on The Real Real, if you’re interested. Looking back on my many travel stories, I realize I take this dress a solid 75% of the time I travel because it’s comfortable, appropriate for everything, looks good with tights and boots or a kitten heel, and serves as a good base for most weather.
I styled it with a Toteme Glossed Leather Belt ($410) that wraps around one’s waist twice, my lowest heels, Jamie Haller’s The Kitty Points ($595) in maroon suede, and my Burberry coat, which was the right choice for this trip! Lots of folks said it wasn’t cold enough for a lightweight wool coat, but it was quite windy, so a trench wouldn’t have been enough for me and my weak Southern California blood. The work bag is the same as ever, a Mansur Gavriel Large Leather Tote ($655) that I’ve owned for well over a decade.
Office Day 2: This was my favorite look of the week, mostly because I’m madly in love with the Guest In Residence sweater I wore. I’ve talked about this a lot, but wanted to call it out again, because I think it's a good note. Pack outfits you already know, love, and have wear-tested when you’re going on a work trip. There’s nothing worse than feeling fidgety in a meeting because you’ve got an itchy new skirt on, or trousers that look great when you’re standing, but feel uncomfy when you’re sitting.
So on that note, I pulled a few of my favorite pieces: A black leather Ulla Johnson skirt (sold out, but a similar version here) that feels like butter, a vintage Carven blue-and-white button-down skirt I got from the expertly curated NYBRED LATHREADS ecommerce store, my go-to Dior J’Adior Pointy Slingbacks ($1090), which have the dream 2.5-inch heel for work, and my current most beloved item: a Guest In Residence Shrunken Pointelle Crew Sweater ($265) in Lemon.
Friends, when I tell you this is an excellent sweater, I am not kidding. It’s truly the softest sweater I’ve ever touched, and wearing it feels like a hug from your best friend. It’s on the thinner side, and has the most adorable pointelle detail, that screams spring, plus the color is an acidy yellow that feels like it has a hint of chartreuse in it. The whole thing feels elevated as hell, and I cannot recommend it strongly enough.
Office Day 3: By Thursday, I was feeling a bit worn down. Day one had been mostly 1:1 meetings with my UK-based leadership team, which was quite exciting and fun, as we could talk about the brands that are under my umbrella, like Wallpaper*, Who What Wear UK, Marie Claire UK, and Country Life, as well as Homes & Gardens, Livingetc, Guitar World, Louder, and more. I have phenomenally talented colleagues, and love getting face time with them.
Days two and three were really interesting in very different ways, as they were dedicated to our executive leadership team summit. It’s an honor to be a part of this group and tackle the larger company strategy, but summit days are also a bit like drinking from a firehose. There’s so much information to absorb and process, whilst also fighting jetlag, and it made my brain spin, to put it mildly.
So for day three, I just needed to feel cozy, and that meant comfort pieces, specifically my go-to AE77 Premium Barrel Trousers ($41.40 on sale now; normally $138) that I have in black/size 6. To be quite honest, I never expected to like a pair of American Eagle trousers so much, but I ended up buying several pairs because I love them. They’re very slightly bow-legged, so I think they’ll age well with any trend cycle, and are a wool blend, so they’re lightweight and don’t wrinkle. I wrote about them in the beginning of March, when they were on sale for $55, and I’m shocked to see the price is even lower. I think they’re an insane value for the price.
I styled them with a J.Crew Featherweight Cashmere Cardigan ($158) in Citron Green—clearly I like a strange green/yellow color—which I have in a small and love, as well as my trusty Khaite Ross Jacket ($588 on final sale) in a small, the aforementioned Jamie Haller heels, and my standard Valentino Vain Bag ($4490), which was the only bag I brought and fits nicely in my work tote.
That evening, I changed into a J.Crew x The New Yorker gray cashmere sweater and my Jamie Haller loafers, as I went to meet up with my former boss, who is now the Chief Commercial Officer for The Royal Ballet and Opera. I met her at The Royal Opera House and she generously took me on a backstage tour of the entire building ahead of that night’s opera, and it was so incredible to see the phenomenal sets, costumes, and see how these world-class teams make artistic magic happen every single day. Friends, I might have cried, I was so moved. What else is new?
WHAT I GOT RIGHT / WRONG
Let’s start with the wrong! As always, I packed more stuff than needed, including an additional pair of black leather Jamie Haller heels (two sets of black heels for three days is peak brain fart), some vintage t-shirts that just sat in my bag, and the aforementioned Roksanda skirt that was unnecessarily formal for internal meetings. Better for when I have to present to our board or have external meetings. Hopefully I remember for next time.
As for what I got right, those Jamie Haller loafers are absolutely the move if you have a lot of walking. (Also, they’re on sale at Shopbop, which rarely happens). They’re dreamy for domestic and international flights, as they’re so soft they fit your feet when they swell and contract, and are comfortable for city walks too. Once again, they’re absolutely a 12/10 purchase. Also I truly love my Guest In Residence sweater; the color is so fashion, the fabric is so insanely soft, and it just makes anything you wear look better.
Also, I’ve written about it before, but I used my Timeshifter app again for this trip, and unlike in previous trips, I actually followed it perfectly, against my natural instincts. That meant getting on the plane in LA at 3:30 p.m. and immediately going to sleep (with a little prescription help, ahem). I ate a big lunch right before leaving for the airport, brushed and flossed my teeth, and had a clean face, so I didn’t have to eat or get ready on the plane, and friends, it was amazing. I woke up at 9:30 a.m. London time, drank a boatload of tea when I got to the hotel, and did walking meetings in Hyde Park, so I got tons of sunlight, all per the app. I found it easy to wind down at night, and got a full eight hours all three nights I was there.
Coming back, my flight left at 10 a.m., and once again Timeshifter told me to go to sleep basically the second I got on the plane, which I didn’t find problematic, as I hadn’t had any caffeine that morning. I slept for a solid seven hours on the flight, got home by 2 p.m., and managed to stay awake until 8 p.m. on Friday night. Slept for over ten hours that night, and I’m feeling cautiously good. Long story long: It works!
(Normally I take a 1 p.m. flight out of LHR, which means a shorter time of having to be awake in LA, and I think that probably works a little better for me, but this was nice because I was home by the time my kids got back from school.)
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.
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As someone who has had many a fashion meltdown, I feel so seen, down to the absurdity of it all. But there’s something to be said about feeling prepared and feeling your best and that often starts with how we present ourselves to the world. Also now thinking about how a bitchy little heel and a cunty little bob when paired with a power shoulder is basically Katherine O’Hara in Home Alone.
I’ve had a full time WFH job since 2010 interspersed with 3-5day trips usually 6 times a year. Some years more travel, some years less. I have always told my kid the day before a trip (less time to build up angst) and promised a fun souvenir when I’m back. My kid melted down HARD when I called from the road before age 8 so I ghosted or called only after bedtime. We were pretty matter of fact over work travel and treated it like any other thing my kid didn’t like but still had to do and had a similar script. ‘Mom travels for work because it’s part of her job, and she likes her job. Mom’s job also lets her work from home so she can drop you at school/get you off the bus. I know you don’t like when I go away but I always come back and I will always spend lots of time with you when I do. Do you want to plan something special for when I come home?’
My husband works full time in an office so my kid also realized he still got a lot more facetime with me when I was home.
At the end of the day, I like working, I like work trips, and the salary benefits my family so I try to let go of the guilt as much as I can. Plus when they get older you can (sometimes) bring them along which is very cool! I also brought my family on a work trip where I knew I’d be working insane hours. They had fun while I worked from 7am-midnight which proved to my kid that yes, I really was working long hours and not just going to fun places and having adventures alone.