On Island Time
When your new life meets your old context
They say you can’t ever really go home again…but what about your second home? What’s it like to slip back into a lifestyle once inhabited, in your present day form? That’s exactly what I’ve found out this week, during our visit to my former island home, Bermuda.
For those new here, my husband was born & raised on the tiny subtropical island affectionately dubbed “The Rock.” I lived in Bermuda for nearly three years, from early 2017 to late 2019, before moving back to Southern California. If you’re surprised to hear this—you’re not alone. Bermuda is a very unique place to live, one that if you’re lucky enough to experience in your lifetime, is sure to change you forever.
Returning now, it would’ve been easy to slip back into the exaggerated island version of myself I once embraced here. (Any excuse to buy some Johanna Ortiz or Cala de la Cruz, honestly.) But instead of building some elaborate “resort wardrobe,” I packed the clothes I wear almost daily back at home, in a palette of mostly white, brown, and navy—nary a palm tree motif in sight. And oddly enough, that felt more natural than ever. Less like I was dressing up for a fantasy version of island life, and more like I was fully at home in my own skin—even while returning to the site of former said island life.
I tend to pack in pieces, not outfits. Meaning, I bring a set number of tees, tops, pants, etc. that I know will all coordinate with each other, and make outfits while on the trip instead of pre-packing looks. This is mainly bc I almost always end up changing my mind on the outfit I had planned in my head a week prior, so packing in this capsule format affords more flexibility.
Here’s how it all came together over the course of the week—and some findings I had along the way.
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TRAVEL DAY
Traveling with kids should be an Olympic sport. Luckily they’re the age now where they can generally tolerate a long-ish flight. Comfort is always key when I’m traveling, so I opted for some of the best Lululemon pants I own (thank you Reva), a white sweatshirt (more on this soon), and my trusty Bensimons—aka “French Keds.” I wore my gray Leset Margo tee underneath it all bc layers while traveling are clutch.
As for bags, I brought my small BV Andiamo for its ability to be worn crossbody or as a shoulder bag, as well as my The Row Margaux black inside-out bag (one here in red suede), bc I have yet to find a better carry on catch-all that looks as good as it travels.
DAY 1: NYC LAYOVER
Surprise! We snuck in one day in NYC, primarily as a long layover of sorts. We always take any excuse to see our NY-based friends, and breaking up the long trip helped the kids better acclimate.
The weather was chillier than I was expecting, so I brought along this Gucci coatigan that I scored on mega sale at Elyse Walker last season—the perfect summer jacket. (One here, similar here, and this would also get the job done). I paired with my Attersee navy linen pants and my fave white tee of the moment. I feel weird wearing flip flops in the city, so I opted for my Emme Parsons ivory sandals—the total star of my trip! They paired so beautifully with everything I packed, I’m convinced everyone needs a pair of ivory sandals. Mine are no longer, but I love these AGS, these from The Row and this from Ref.
We stayed with our dear friends in Westchester, and took the train into the city for a few hours Saturday morning to catch up with friends, show the boys landmarks like Central Park and Bergdorf Goodman (haaaaa), feed them their first-ever NY slice, and then back to the burbs we went for a BBQ at and early bedtime for our 6am Uber to JFK.
TRAVEL DAY/DAY 1 IN BERMUDA
I wore the same travel outfit to Bermuda (I was able to wash it at our friends’ house!), and upon arriving, changed into the above look for an at-home BBQ with my husband’s entire family. I am sometimes reticent to pack prints for a trip—they’re more memorable and perhaps slightly harder to rewear, but I also think at least 1-2 simple prints can add a little dimension to your vacation outfit-building process.
DAY 2
We headed to Rosewood Tuckers Point Beach Club, which is fabulous and worth a stay at the hotel to access (our family are members). It was slightly overcast upon our arrival, which is why I threw on my old Interior Bruno sweater over an Else swimsuit and Leset Niko pants. I cannot stress how valuable an open knit, lightweight ivory sweater like this can be in the summer months. If I didn’t own, I’d snap up this from Another Tomorrow, but I also love this and this from J.Crew—both more affordable. The drapey knit white sweater is the perfect summer piece: you can throw on over your swimsuit on chillier days, wear with shorts and pants, even use as a third piece around your waist or shoulders.
As for accessories, I wore my Janessa Leone Waverly hat, Hermès Chaîne d'Ancre sandals (found these for you!) and Panier de Plage red tote I scored on Poshmark a few months ago. The pop of red was necessary this trip to counteract all the neutral pieces I packed. My general rule of thumb: always pack one unexpected item (usually safe to do so in an accessory) to throw your outfits just a smidge off-base…no one needs to look like a perfectly coordinated campaign shoot while on vacation. Make it yours!
We had dinner at my in-laws that evening; they’re very casual so I opted for ease & comfort—pajama dressing at its best. I own this Toteme top & pants set, but left the pants at home and brought this pair from Leset instead; I figured a simple white pant would be more versatile than one with a motif. I was right!
DAY 3
It poured absolute buckets all day long, so we decided to visit the famous Crystal Caves. I just kept thinking to myself how chic it would be to host an intimate dinner inside the caves. Fun fact: one of my absolute favorite Real Housewives scenes of all time was filmed in a Bermuda cave, albeit at Grotto Bay: “RECEIPTS! PROOF! TIMELINE! SCREENSHOTS!”
When it rains on a subtropical island, it’s still pretty warm, so I paired my vintage white pull-on shorts (similar here) with my slinky Khaite button-down and Bensimons, given the weather.
DAY 4
Boat day! We rented a pontoon boat to give the kids the full Bermuda experience. We left very early in the AM so it was chilly; I paired my Attersee linen pants with my Polo sweatshirt. Underneath it all: my new Else swimsuit*…yes, the same style as the red one I wore to Tuckers, but in black. If it ain’t broke…
So much of my “courtship” (lol) with my husband consisted of us cruising around and having fun on boats—our wedding officiant (my husband’s best friend) even joked during our ceremony that we fell in love on the water. He’s not wrong!
Every Wednesday night in the summer, Bermuda hosts Harbor Nights, a street fair featuring local artisans, food stalls, and cultural performers—including the iconic Gombeys. It was a little chilly and possibly due to rain, so I reached for the only dress I had packed—my Maria McManus shirt dress (similar here, but also swooning over this)—along with a Toteme shawl/sarong I had brought as an extra layer for the plane and the best summer sandals in the biz. (Sadly she no longer makes the gold ones I own, but any of these colors would do the trick.)
Added these new CompletedWorks earrings* and out the door we went! Obsessed with the mismatch.
DAY 5
Another rainy day…gah! Since I lived in Bermuda for three years, I’m used to these bouts of tropical weather—but it was a bummer for the kids, who just want to be outdoors. I leaned into stripes with the Gucci coatigan, my gray Leset Margo tee and Lou Lou de Saison shorts.
No matter, we made the best of the day. We had lunch at 1609 (the year Bermuda was settled!) at the Hamilton Princess, which boasts one of the most impressive art collections on the island. Our friends are the owners, and they’ve been collecting art both personally and for the hotel for year—it’s always a treat to see what works they’ve added.
After lunch, the rain let up and we strolled Front Street, making our way into one of my favorite stores on the island: The English Sports Shop. It’s so old-school Bermuda-meets-UK preppy (they don’t even have a website!), and I always snag one of their men’s crewneck sweaters when I stop in. This time: the white.
Speaking of menswear! My husband lives and dies by two brands these days: Peter Millar and Collars & Co*. He packed nearly exclusively the latter for this trip and it served him well. If you’re ever on the lookout for great resortwear for your husband/bf/partner/dad—check them out. It packs easy, features wicking materials and they have tons of vacation-friendly colors & patterns.
We had a quiet dinner at home, and a few old friends stopped by to say hi, which was lovely. The rain finally stopped, and I changed into my Attersee sheer button down and Niko pants with the Emme gold sandals.
DAY 6
Our last day! It was sunny and ‘Bermudaful’ weather, as the locals say, so we headed to the Princess Beach Club, where I wore my Eres swimsuit (comp), Leset Niko shirt, and Sézane pareo* (sold out, but dreamy comp), all paired with my Chaîne d’Ancre sandals. One funny thing about packing in a tight color palette is that you end up making combinations you might not at home—like a navy shoe with an outfit featuring zero navy. But that’s part of the fun. Without the full reign of my closet, things get a little less coordinated and a lot more interesting.
Before I go—a couple key learnings from this trip (refining our packing strategy is a lifelong journey!):
I wore every single article of clothing I packed—a VERY rare feat for me! There were a couple of moments I wished I had one extra pair of shorts or top, but on the whole, I made it work. Proof that we can do just as much with less.
I forgot how casual life on the island is. I packed a gorgeous beaded clutch for a sunset cruise that sadly got cancelled due to rain. Otherwise, I didn’t touch it; you really don’t need ‘fancy’ things on tropical vacations.
This trip made me realize I’m in desperate need of a solid brown swimsuit in my repetoire…after all, I’m all about brown this summer. I have my eye on this deep espresso brown, this one piece* (love the chain strap detail), this 90s-coded square neckline maillot, or this classic tank style*.
I’m going to say this as gently as I can: I adore my kids, but traveling with kids is not a vacation. Still, I love making memories with them, and seeing how much they enjoyed the many new experiences this week makes it all worthwhile.
As you read this, I’m on a flight back home to California, exhausted, ready for my own bed, excited about the several packages awaiting my arrival, and very proud of myself for not morphing into some ‘boho chic’ version of my former life just bc I was transported back to an island. I felt like me this week…just looser, easier, and more relaxed. It reminded me of a quote from Irene Kim (김애린)’s letter yesterday:
If you feel like yourself wearing an outfit at home, chances are you’ll feel good about it on vacation, too!
Bermuda may have been the setting, but for the first time in a long time, it didn't dictate the character. And that's probably the best souvenir I could've brought home.
Thank you for reading…until next week!
PS: If you’re headed to Bermuda this summer and need any additional recommendations, my DMs are open! I would be more than happy to answer any questions or offer advice on where to stay, what to do, etc.
AFN discount codes for brands linked above: Goldie (SOGOLE15)
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*Occasionally brands send me gifts or incentivize sharing links for a nominal fee. I will always note these with an asterisk, but I would also never feature anything I don’t love and wear on the regular.
“Bermudaful” really is the only word for all of this 🤍🌞
I love love love a white or cream sweatshirt. I just received the mother sweatshirt. It is so soft and cozy.