7 Things I Packed (For Our First Major Family Vacation) That Exceeded My Picky Expectations
Including a drugstore mascara that shocked me it's so good.
Hi everyone! Skipped last week’s installment due to spring break—thank you for the kind messages; I’m glad you missed this newsletter, or at least noticed it wasn’t in your inbox—and I’m just getting back into the swing of things, so this is going to be a short (for me, anyway) one. [Editor’s note: It’s not short, actually.]
Historically, I haven’t taken a ton of time off, and I’m trying to work on that. For the first sixteen years of being an entrepreneur, I never felt like I could relax, aside from when we gave the whole company time off at the end of the year. (Plus for the first eight years, I was too broke to go anywhere.) After selling the company two years ago, it took me a minute to adjust to my new, expanded role. That huge shift, plus having two small kids and a husband with his own wild work schedule, meant I have become vacationally rusty, if you will.
Very rusty.
At the same time, whenever I find myself in a (lightly or otherwise) challenging situation, the second it’s over, I immediately feel a compulsive need to run the experiment again. Is this a Virgo thing? A founder thing? Unclear. For the record, I don’t mind this compulsion; it’s partially the reason I have two kids, and definitely the reason I wanted three. So while I’m not heading out on another amazing holiday any time soon, I figured writing this newsletter might do the trick? If nothing else, it’s a reminder of what worked and what didn’t, and hopefully you all will share some of your favorite travel/packing tips and tricks too?
#1 lesson from this trip: Half the joy is the planning, which wasn’t expected! There’s a 2010 study that gets quoted quite often, that found that happiness is often highest before a vacation. Anticipating and planning a trip sparks joy for many people, and I’m happy to learn I am one of those weirdos. Historically, I rarely plan ahead, as I worried I’d feel let down by the actual event. I’m not sure when this changed for me, but I spent much more time thinking about this trip, and that gave me months of joy.
(This trip was also a particularly special one, as we were celebrating my parents’ 50th wedding anniversary. Rather than a party, my mom wanted to take a family trip to Hawaii, which is her favorite place in the world and holds special meaning for us all.)
Another thing that worked out well for me? Packing ahead of time. We left for Hawaii on a Friday, and I knew that week leading up to departure was crazy with a board meeting, major upcoming project, and lots of podcast stuff to record. So while it felt annoying, I spent the weekend before our trip packing, and I was really glad to have that time. We were still racing against the clock to get everything done, but I can’t imagine how stressed I would have been if I had waited to pack.
As for packing: This may come as a surprise, but I’ve never been a fan of buying new things for warm-weather trips. Most of my vacation clothes are well-loved staples I’ve had for years, like this linen dress from Reformation, which I own in black and a floral print. (It’s available in sizes 0-24 and holds up really well; I bought my black one ages ago, and it still looks and fits like it’s brand new.)
The other reason I don’t want to “go big” in terms of holiday clothes is weird, but true: I don’t want to be perceived on vacation. I don’t want to take outfit pics. I don’t want to do my hair. I don’t want to be “on” in any way. I just want to be off my phone and with my family, with a side of reading in the sun. (No judgment though! I love seeing other people’s outfit pics! I love vacation content! Truly.) That said, I found a couple of new things that worked really well (drugstore mascara!), and am happy to share them today. Hope you enjoy!
As always, if there’s an item you’re shopping for or you need help sorting through the zillions of options out there, please don’t hesitate to drop me a comment and I will add it to my to-do list. (And why am I prompting you to comment? Because while I love DMs and always try to answer you there, my inbox is messy, and comments here are much easier for me to find and use as source material as I’m working on new things. Also, I love comments; they make me feel seen.)
VACATION WINS
The pieces that I can recommend 100% without reservations.
Left On Friday Sunday Top ($95) and High Tide Bottoms ($95)
I knew I liked this suit (as discussed two weeks ago) simply from trying it on, but I didn’t fully realize how amazing it was until I took it to Hawaii. My four-word review? This suit is perfect. Yes, it’s great as an actual swimsuit, but it’s also weirdly versatile. I wore the top as a sports bra with my go-to inexpensive workout leggings when I went for a long beach walk and it was so supportive. I also wore the suit under a relatively sheer Doen dress, and it worked beautifully there too. The suit is 100% a hero piece for me, and I think it’s actually my new YCOHO swimsuit. Actually, I know it is. This suit is truly it.
Birkenstock Arizona Suede Sandals ($140) in Mink
I own lots of Birks, but after years of testing, I think the version I can recommend most wholeheartedly (for vacation and real life) is the suede Arizona in this warm brownish color. It’s a nothingburger of a hue, so it really goes with just about everything. I wore mine 98% of the time I was in Hawaii, as they work equally well for the pool, beach, dinner, and beyond. If you want a pair with a little more personality, The Great makes a paint-splattered version that I own and love.
J.Crew Cotton Voile Beach Shirt ($79.50) in Black Dot
I’m a longtime fan of the brand’s oversized beach shirts, and couldn’t resist picking up this polka-dot print version in a super airy cotton voile. To contradict my earlier statement, I also bought the Side-Tie Cotton Voile Skirt ($79.50) and am equally fond of it. Someone somewhere on the internet said this skirt would also work off the beach, and I don’t know if that’s exactly true. It’s relatively sheer, and I personally wouldn’t wear it to work, for example. One way to make it functional for non-pool situations is to wear the shirt over the skirt; it’s a voluminous silhouette, but I loved how the two look together, and it’s also a bit more opaque that way. I felt like a Kusama queen in these pieces, and hope you do too.
L’Oreal Paris Voluminous Panorama Volumizing and Lengthening Mascara ($13)
Y’all yell at me for never including drugstore picks in this newsletter, but I have one for you today! I stopped by Target to buy more of these mess-free coloring books for the kids for the plane (big fan!) and randomly picked up this mascara while I was there. Holy moly it’s good! The wand is tapered, so you can really get all of your baby lashes and into the corners, and the formula is truly impressive. Voluminous lashes, a long-wear, smudge-resistant formula, and it is deeply pigmented (I have it in Blackest Black). I was truly delighted and very much recommend it.
Veken 8-Set Packing Cubes ($20)
I bought two sets of these packing cubes (blue and pink, per their request) for the kids, and honestly that might have been one of my smartest purchases. Packing two kids for a week-long trip involved more gear than I imagined, and these cubes kept things very organized and make my life much easier.
BabyGap Print Rash Guard Two-Piece Swimsuit ($26)
I love a UPF 50 swimsuit with sleeves, as it means I can apply sunscreen to my kids slightly less often. Historically I’ve always bought my daughter long-sleeve one-piece suits (she’s obsessed with the floral print on this one), but it makes her frequent bathroom breaks kind of a hassle. This time around, I bought her a rainbow long-sleeve rash guard two-piece suit, and it was a total game changer for both of us. Easy to get on, easy to get off, and it’s also cute. I’m forever converted.
La Coqueta Kids Sofia Leather Sandals ($78) in Gold
Finding shoes for my daughter isn’t a breeze, so when she decided she liked these soft leather gold sandals from La Coqueta, I was thrilled. She’s been wearing them to school—usually styled with thin pink socks, per her request—and we decided to take them on this trip, and I’m so glad we did. She wore them everywhere, as they’re so soft and comfortable.
VACATION MEH
Honestly, I felt so unbelievably lucky to go on this trip, and wouldn’t change a thing. That said, I wouldn’t recommend flying Hawaiian Airlines out of LAX. This is not a knock on Hawaiian, for the record. The flights were great and the crew was lovely. However, right now you have to check in for the trip in the international terminal, but then your flight gate is actually in another terminal, so you have to walk one million miles to get there. If you’re traveling with two little kids and two grandparents (one of whom has a heel spur), it’s not ideal.
It’s more frustrating on the way home, especially since we got in pretty late. It was a serious hike to get from the gate to baggage claim, and took us the better part of 45 minutes. Again, this is fine for me and honestly I didn’t mind getting so many steps in, but something to consider if you’re traveling with small kids and grandparents.
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.
Another great newsletter! TY. For the record, I missed your newsletter last week. How can I find a grownup version of Wilder’s sandals?! They are adorable.
I love your remark around not being ‘perceived’ on vacation- I’m the same way! I always feel weird that I just don’t care enough about how I look or what I pack when I’m away. I care a lot about how I look and how I’m perceived in my day to day life in NYC and at my job; vacation is a needed break from that mindset!