Everything I Packed For 48 Hours of Work + A New York Wedding. I'm Actually Quite Pleased With Myself!
Plus the book you need to read, the show you need to see, and more progress on my flying issues.
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Hi everyone, and welcome back! I’m currently writing this whilst en route back to Los Angeles from New York, where I’ve been for the last couple of days for both work and my amazing colleague Nikki Ogunnaike’s wedding. To say she was an exquisite bride is the understatement of the year, in no small part because she was styled by the peerless Shiona Turini, a combination that embodied excellence on every level. While I’m not going to give you much in the way of wedding details—that’s for Nikki to share—I will say I did a pretty smart job of packing for this trip, and truly believe the secret to work travel (maybe life?) is finding dresses that don’t wrinkle. More on that, below.
Before we discuss the highs and lows of my packing, I just wanted to make the case for a couple of things I think are worth your time.
Jessica Knoll’s new book, Helpless ($25)
As a longtime fan of all things Jessica Knoll—I had the great pleasure of interviewing her for Second Life back in 2022 and think the episode is well worth your time—picking up her newest book was a no brainer. (Full disclosure: Jessica sent me an advance copy with a note that simply said, “Buckle up.” But I liked the book so much I bought two copies so I could give it to a couple of friends, FWIW.) When I tell you I inhaled this book in a single day, I’m not joking. About halfway through I had to put it down and take Snacks for a walk, just so that it would be over too quickly.
All the critics are calling it a “sexy thriller” and what happens when “Gone Girl meets 50 Shades” and I’m here to say those comments are pretty accurate, but don’t fully capture Jessica’s brillance. The story is twisty and suspenseful without being horrifying or gory, and definitely darkly horny. And yes, that felt a little awkward to write because I know many of the readers of this newsletter in my professional life, but sometimes you have to just say the true thing. Anyway! Go buy this book; it’s the best thing Jessica has written, and that’s saying something as she is a New York Times bestselling author of a lot of damn fine books.
Lucky (streaming now on Apple TV)
Loosely based on the bestselling New York Times and Reese’s Book Club Pick novel by author Marissa Stapley, co-written, produced, and created by Jonathan Tropper and (my friend!!) Cassie Pappas, and starring Anya Taylor-Joy, Drew Starkey, Annette Benning, and my favorite Timothy Olyphant, I am deeply thrilled by this show. It’s higher stakes than my usual go-to recommendations, but it’s a truly thrilling heist-gone-wrong, con-on-the-run show that I think is worth a mini binge. Three episodes are out now, with a new one coming this week!
72 Hours In New York / 8 Work Meetings + 1 Rehearsal Dinner + 1 Wedding
For this quick trip to New York, I had to figure out a way to cram two formal dresses and ensuing accessories into my suitcase, plus a travel outfit for the return flight home, something for a work dinner, and looks for two days of in-person client meetings. This isn’t so hard, but the social events add a layer of additional items, as they a) simply require more room than a standard outfit and b) need different shoes and bags than I’d normally pack. Plus New York weather is often a mystery to me, and was forecast to be hot, but inside spaces are always so damn cold (complimentary). As always, I don’t like to buy new clothes for work trips, because the last thing anyone needs in a pitch meeting is feeling fidgety in one’s clothes. Nope.
Travel Days: I wore basically the same thing for both travel days, and totally forgot to take a photo of it. Do you remember how I’ve said like a zillion times that I own two pairs of the Banana Republic Barrel Leg Pull On Pants ($84.99 on sale now)? Well that came in handy, because I wore one pair to New York, and the other on the way home. Styled both with gray t-shirts (The Great’s boxy crew there and a vintage one I stole from my husband on the way back), leopard Jamie Haller loafers, and my now beloved and very tested Alex Mill Painter Jacket ($250) in the most perfect blue known to humanity. (I sized up to a medium for the jacket, which is boxy and slouchy that way.) This jacket has four pockets, making it ideal for travel, and it’s machine washable and super soft.
Work Dinner and Meetings
After landing on Wednesday evening, I walked to a really fun dinner at The Corner Store, where I ran into a slew of delightful former colleagues and friends whilst there. FWIW, The Corner Store makes a mean French dip sandwich, which I strongly recommend. For this dinner, it was so hot out and I was walking, so I wore a black linen Reformation Birdie Dress ($298), which runs a little va-va-va-voom when you sit down, an older pair of Jamie Haller Double Buckle Sandals ($595), and my older suede Chloe Small Bracelet Bag ($2950), which is similar to this one and has been a real winner in my book. Overall this look is easy and worked, so I’m glad I packed it.
Thursday: The next day I had back-to-back in-person meetings with clients, and not knowing if the heat was going to be as bad as it sounded. Spoiler alert: 80 degrees in New York is not the same as in LA. It’s so much better and lighter. I love a midi length, sleeved, print dress for work, especially in a non-wrinkley fabric, and so this Rixo Meg Leopard Polka Dot Dress ($415) was ideal. I didn’t need a sweater, the print combo is so fun, and it works for my work, so that’s a 10/10. Wore it with my “walking slingbacks,” which are Amina Muaddi Holli Slingbacks ($760), which are a treat, and my Jamie Haller tote, which is sadly sold out. Side note, I really love her new The Ledger Bag ($1395) in Olive, and have a feeling it’s going to be my next splurge.
That night, we had the first event for Nikki Ogunnaike’s wedding, which was a cocktail party in Brooklyn. I wore an older Rebecca Vallance strapless dress that has a corseted bodice and a full skirt, with the same Chloe bag and an old pair of black suede Paul Andrew peep-toe mules, that I wish were part of the permanent collection. (Staud makes a similar style at a better price, iif you’re interested.) I made an amateur mistake and didn’t ask about the party’s ground covering, and I wish I had! If I’d known, I’d have worn the Amina Muaddi’s instead, because they’re much easier for navigating grass. Learn from my mistake! Also, the Rebecca Vallance dress no longer is on the market, but I also have the Narcissa Dress ($815) and love it, which is the same material, though a different cut.
Friday: The final stretch! I had more in-person meetings on Friday, and I’m pleased to say my formula worked again: Print dress with sleeves and a midi length, in a non-wrinkle-forward fabric. On this day, I wore a very old Rodarte dress because it’s perfect for any weather and occasion, doesn’t require steaming, and you can change it up with accessories. I added my Khaite studded belt to play off the sweetness of the floral print, and stuck with my previous day’s accessories.
And that night, I got all dressed up because my husband (who flew in late Thursday night and back to LA with me early Saturday morning, and is a real hero) and I had Nikki’s wedding in Brooklyn that night. I won’t spoil the details of her amazing wedding, but trust me when I say it was magical. (Also, I will say this: That was one of the most stylish, delightful, love-filled weddings I have ever been to in my life. It was an honor to witness and be in the company of such a brilliant couple, who have the most phenomenal friends.)
After much debate, I ended up in a dark teal and lilac one-shoulder dress, specifically Roksanda’s Maite Cocktail Dress ($1720), which is lightly outside my style zone in terms of silhouette. As you might have picked up by now, I feel most comfortable in a strapless evening gown, and have never done something with a single shoulder, let alone a cape accent, but my friend Katie and my husband both approved, which gave me the push I needed. I first started buying Roksanda after I went to one of the brand’s shows during London Fashion Week, and I think her stuff is really well done. The fit is always for real, actual women, the colors are painterly, and the fabrics are great. It’s not expensive, but I have Roksanda pieces for well over a decade that I wear often a still look brand new.
Last thing on packing: I recently purchased this Open Story 7-Piece Packing Cube Set ($35) and honestly, it’s a real winner. They have a compression aspect to them, so they really allow you to maximize your suitcase space!
Flying: And before I go, a quick update on my fear of flying progression. I’ve now had roughly four sessions with my therapist, who specializes in phobias of all kinds, and I am really impressed with how much better my anxiety is already. As I mentioned last week, before flying to New Hampshire with the kids, I was extremely uncomfortable that whole week, and the flight itself wasn’t ideal. However, I was able to enjoy myself whilst there, which was new for me, as my anticipatory anxiety has made it impossible to enjoy a trip, knowing that a return flight awaits me at the end.
Traveling to New York this time was even better, which I assume is because a) the flights were less turbulent and b) I wasn’t flying with my kids, so it fundamentally felt easier, as I didn’t have to mask my concerns. Also the simple act of examining my fear feels like it’s slowly deflating it, and starting to unpack my control issues!
I’m also using the Headspace app and listening to their fear of flying episode for 10 minutes before taking off and then during take off, which is nice and soothing. Additionally, I have some backup lorazepam in my bag, which I used extremely conservatively when traveling to New Hampshire, and not at all on this trip to New York. I think knowing that I have something if my panic starts to spiral really helps me feel equipped, psychologically, even if I’m barely/not using it. I guess this is a longwinded way of saying: I’m glad I’m geting help, and I hope anyone else going through this gets help too. It’s amazing, truly.
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.
One of my favorite ways to start my Sunday morning!! The leopard x polka dot combo is a dream!! HK, you looked 11/10 in all of your outfits. Thank you for sharing with us! 🖤
Could not at a TRR saved search fast enough for that STUNNING one shoulder dress. Also I know it gets mentioned but I love how the through line in so many of your outfits are items you’ve talked about and worn for years! Truly! It’s so good to see wardrobe staples and rewears.