Bite-Sized: The 3 Week Carry-On
multiple cities, climates and no shortage of outfits
From time to time, I’ll take a break from our regularly scheduled programming of recipes and entertaining tips and invite you to travel with me. Think of these as Bite-Sized guides to the places I visit, covering everything I manage to do in 48–72 hours in a city.
Travel is pure inspiration and creative expression for me—from the restaurants and wine bars I seek out to the wardrobe I finally have an excuse to wear outside of Los Angeles. Writing about these things feels less like work and more like I’ve woken up with an entirely different career for a few days, which is a rather fun exercise.
I’ve got my packing—usually in a carry-on—down to a science. Admittedly, it’s often questionable size and weight, but when you travel as frequently as I do, often changing hotels and staying with friends every few nights, hauling a large suitcase from stop to stop becomes exhausting. So I make it work and simply make sure I’m in an early boarding group.
After nearly a year of living out of a suitcase last year between a long stretch back living in New York in 2025, and frequent trips to Europe to see my man, I became far more creative with my personal style. Not because I had many options, but because I had fewer. I was forced to make things work, repeat outfits, and stop overthinking. Somewhere along the way, I learned to care less, utilize the “wrong-piece” theory which is perhaps the closest thing to a formula for that je ne sais quoi of personal style.
These days, I dedicate a surprising amount of brain space to packing well, so I don’t fret when I’m there. About a week before a trip, I pull favorite pieces onto a garment rack and let them live there for a few days. I try on everything, take photos. Then I edit. I text photos to my mom. We edit again.
My rule of thumb is simple: pack half the number of outfits as days on the trip. Two weeks away? Seven outfits. Three weeks? The same seven outfits. If it works for two weeks, it will work for three. Keep shoe and bag options to a minimum, I find its helpful to try on every outfit with the same few accessories and edit from there. The only exceptions are event-specific pieces and sport-related necessities—a cocktail dress, sport-specific gear, and the like. I always pack a few tried and true statement pieces that rotate by the season. This trip it was — my fringe suede jacket, a chunky knit, this Zara t-shirt, funky silk pants, shell necklaces, tassel belt, basket or beaded clutch. Those key pieces become workhorses next to staples like my vintage Levis, slip skirt or dress, long denim shorts…you get the idea.
For accessories in summer, I keep things equally restrained: two or three pairs of sandals, ballet or mesh flats, comfortable walking shoes (for me that’s boat shoes or lace-up flats—I’m simply not a sneaker gal), and one pair of workout sneakers, these pack surprisingly flat. One handbag and one clutch are usually enough, though every now and then I convince myself I need a second bag and inevitably use only one.
I was once a die-hard packing cube person, but I’ve found they add weight and limit how creatively things can be folded into a suitcase. Muji makes the most lightweight one. Now I use just two: one for t-shirts and delicate clothing, and another small one for lingerie, socks, and pajamas. This jewelry roll is the best I’ve found, and part of the formula to make the same suitcase feel fresh simply by swapping the accessories.
Until recently, I always traveled with an oversized canvas tote—an LL Bean Boat Tote or my Rue de Verneuil. But I’ve discovered that when you’re already pushing the limits of a carry-on, an enormous tote perched on top of my roller, it tends to attract attention at the gate. So I reluctantly embraced the backpack. Yes, I feel a bit like I’m headed back to middle school, but it’s organized, leaves my hands free, and makes navigating trains, taxis, ferries, coffee runs, and airport transfers infinitely easier. Best of all, you sail past gate agents throughout Europe without a second glance.
Rather than show you a theoretical packing list, I thought I’d share exactly what made the cut on my most recent journey. Spring travel required a fair amount of layering and creativity. Over three and a half weeks, I went from Los Angeles to the Hamptons, New York City, Madrid, Athens, Hydra, Mallorca, back to New York, and finally home.
Here’s what earned its place in the suitcase, many of the pieces are old, found on TRR, or not online, so I found as many similar pieces or things that have the same vibe. A lot of these pieces are on sale, so shop fast!
The Dresses, Skirts & Fancy Things
This Banana Republic knit dress was by far the most worn piece in my suitcase. It’s from last summer, but similar versions can be found here and here. The Chan Luu skirt and matching top also got plenty of mileage. I packed a vintage Celine shift dress alt here expecting it to be a hero piece, but Madrid was freezing and I only wore it once. A vanilla-colored The Row slip skirt alt here proved far more versatile, dressing up or down with a simple change of accessories. I also packed an Argent slip dress that works equally well for day or night.
The Heirloom silk top, however, never made it out of the suitcase.
Jackets, Sweaters & Statement Bags
My tan-yellow suede Nili Lotan suede jacket was one of the best investments, this and this do the same but without fringe. Another steep investment this Suzie Kondi sweater takes up a lot of real-estate but is just so fun and works with everything, similar vintage here and here. I love a basket bag in summer, this one is carry-on size. I also love this beaded bag.
Pants, Shorts & Everyday Staples
I never travel without a pair of vintage Levi’s jeans, these fit similar. When I don’t want to wear denim, my old High Sport pants are always the answer to an outfit. If you’re looking for something similar, these are a close second.
A patterned silk pant is one of my favorite travel pieces. Mine are from La Prestic Ouiston and are admittedly difficult to track down, but worth the hunt. I also love these and these. And long live the long short mine are Agolde—these shorts are perfect. I always feel cool in them, and they easily transition from day to night with a change of shoes and accessories.
For basics, I packed a rotation of T-shirts from Leset, Buck Mason, and Re/Done, along with an oversized surfer-girl long-sleeve. Mine is from Renggli, but Ref is making a great version right now. I typically bring a tank top or two as well, but skipped them this trip since it wasn’t quite high summer. My favorites remain Buck Mason and Re/Done.
Beach & Workout and Lounge Essentials
With beaches on the itinerary, I packed a pareo, poplin boxer shorts (not essential, but nice to have), one bikini, and one one-piece.
For some people, workouts don’t exist while traveling. For me, they’re essential. I always pack my ON sneakers because they collapse surprisingly flat, along with a Splits59 stirrup legging, Vuori shorts. I often pack Buck Mason sweats, and a Negative Whipped long-sleeve tee for lounging in my tote or back-pack. It’s what I change into on overnight flights when I’m attempting to sleep—though I always switch back before landing.
I love having a lightweight layer to throw on in the morning with coffee or after a shower, so I pack a breezy cotton robe, the Greek Islands are overflowing with shops I found one to be my travel companion this summer, and it takes up almost no room in a suitcase.
What I Didn’t Need
I recently scrolled past this from a stylist on Substack, she said something that stuck with me: don’t pack for every version of yourself. I am absolutely guilty of doing this.
The pieces that were worn once—or not at all—were mostly casualties of Madrid’s weather. It rained nearly the entire time and was unseasonably cold, so many of the spring outfits I had planned never had a chance. Instead, I found myself borrowing weather-appropriate layers from a girlfriend just to get through that stretch of the trip.
The least-worn pieces were a Nili Lotan fringe shawl, Attersee tassel belt, vintage Celine shift dress, Chloé whipstitch cropped jacket.
That said, if I were packing again tomorrow, I’d still bring the Attersee belt. They take up virtually no space and statement pieces that transform a simple jeans-and-tee combination into something eclectic and stylish.
The Shoes
I knowingly overpacked on shoes this trip, but with spring weather and so many destinations they really all came in frquent rotation. Miu Miu boat shoes, alts here and here, these Ref white flats. I could have done with one of these, but got good use of both—Chanel ballet flats in black and white which feel less classic and more graphic and Roger Vivier and scored on TRR and plenty more to be found if you’re patient. One slide sandal, old Manolo Blahnik, one strappy sandal from Emme Parsons, closest match, and Miu Miu beach sandal alt here.
The Souvenirs
No matter how heavy and maxed out on space, I always seem to come home with something. This trip it was a funky brocade jacket and a batik cotton robe, and plenty of salts and spices for my other closet—the pantry.
x Olivia
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