Tomorrow I leave for a Mediterranean cruise with my husband, plus about 400 of his co-workers. His company hosts an annual trip for top sales performers and executives, and though he’s neither, his boss offered him her spot at the last minute. Everyone can bring a guest, so lucky me.
I’ve always opted for slow travel, preferring to soak in a single destination over days or weeks. Recently I’ve even become obsessed with home exchange. I spent my early 20s backpacking solo around South America and Europe, and while these days I lug around nice luggage and car seats, that experience still influences how I approach trips.
The idea of spending only a few hours at a series of dream destinations (in this case, Rome, Naples, Dubrovnik, Zadar, and Venice) sort of kills me.
But it turns out when someone offers an all-expenses-paid vacation to Italy and Croatia, I will emphatically accept. I’ll also contribute to cajoling my in-laws to let us fly them in from Buffalo for the week to watch the kids, who are thrilled about the situation.
While travel is basically part of my personality, I still find packing an overwhelming chore. Historically, I’ve thrown in a set number of tops and bottoms and hoped for the best. But lately I’ve started paying attention to the advice of online fashion folks. Namely: actually planning full outfits beforehand and even trying them on and taking photos. This extra effort (and it’s EFFORT — I have a fresh respect for all the stylish people in the world) has dramatically boosted my confidence and mood when I’m out of town. Turns out I’m just an all-around more pleasant person when I love my outfit.
The cruise itinerary is particularly intimidating, with nightly sit-down dinners, various receptions, and group excursions, so I decided this was a good time to bring in help. I booked a packing session with the brilliant style educator and fellow travel enthusiast Conni Jespersen of Art in the Find, who came over for 90 minutes to get me out of my head. I see it as an investment, since the skills and tricks she imparted will serve me for a lifetime of trips, plus I can reuse the outfit formulas in my daily life.
It was inspiring to see her at work, quickly curating a tight selection of versatile pieces (we both refuse to check a bag) from my closet. She created outfits for each of the activities on the agenda, an exercise that hurts my brain just thinking about it.
Here are all the outfits we came up with for my whirlwind seven days in Europe.
We’re flying from San Diego to Atlanta, where we’ll catch a red-eye to Rome. Conni and I agree on the importance of looking put together when we travel, especially internationally. We came up with a combo of my beloved cotton-linen white trousers, a cozy cashmere cardigan (I’ve started a collection — they’re so versatile!), my favorite little white tee, and a fun shoe.
Stylist Tip: For the long-haul flight, Conni suggested that I change into tapered (for obvious reasons) sweatpants in the plane bathroom. I’ll be using a five-year-old pair of Outdoor Voices sweats that I’ve relegated to pajamas and will put my “real pants” back on before landing.
We’ll arrive around 1pm and check in to our assigned hotel near the airport. I’m hoping our energy levels are decent at this point so we can drop our bags and take the 30-minute train into the city center to stroll around (I’m dreaming of a Trevi Fountain at dusk moment) before sitting down at a restaurant.
Conni suggested this sophisticated get-up using the same pants from my travel day, along with an alternative look featuring heels, in case we don’t end up having time for walking.
It looks like mornings will be chilly, so each outfit must work well both with and without a layer. Conni suggested a leather jacket over a denim vest or a cardigan over the shoulders, depending on the temperature, for another transitional day.
The result is a polished but practical look for the van transfer and first impressions (and maybe a quick cappuccino and cornetto back in the heart of Rome before we set off — I can dream).
Dinner on the Ship: I’ll wear the same pants but switch out everything else.
I’m so excited to return to Naples, a thrilling and chaotic metropolis that I explored on my own for a single, memorable day at age 23. I’m hoping that we can wander the gritty backstreets of the Centro Storico after our guided walking tour and pizza lunch, so I wanted a conservative outfit that wouldn’t draw too much attention (hence the neutral palette).
Dinner on the Ship: I’ll add a jacket and heels
Conni assured me this combo making use of my new pull-on cotton pants is a safe, versatile bet.
Rain Plan: It looks like we might get precipitation at some point, so here’s an option with a hat and sneakers.
We’ll explore the Croatian city on our own before joining an excursion to the seaside town of Cavtat. This will be my first time in Croatia!
I have a couple of variations of the same outfit idea in mind for this day, depending on the specific weather and mood.
Dinner on the Ship: I’ll add the leather jacket and black bag.
I’ve planned a sporty outfit for the morning hike: trail sneakers, tee, baseball cap, sweater tied around the waist, and leggings.
If all goes well, I can carry along a change of clothes for exploring back in town before we have to return to the boat: minimal sandals, a vest, and the black pull-on trouser.
Farewell Reception and Dinner on the Ship: Sub in heels and a red bag.
I’ll recycle my original airport outfit, subbing in a fresh white tee. Our return flight departs at 1pm, but I hope we can steal a few minutes in Venice before jetting off. Maybe a kiss on the Ponte di Rialto or a quick espresso in Piazza San Marco? (Taking me back to a beautiful yet melancholy week I spent alone in Venice many years ago.)
Here’s the full packing list for reference:
Bottoms
2 trousers (white and green)
2 pull-on pants (off-white and black)
Bright A-line skirt
Tops
4 tanks (white and black)
2 white tees
2 button-front vests
Layers
3 cashmere cardigans (yellow, tan, brown)
Leather jacket
Shoes
2 minimal sandals
2 sneakers (casual and trail runners)
1 heeled sandal
Summery flat
Accessories
4 small crossbody bags (red, black, leopard, green)
Baseball cap
Black belt
Now I know how the pros pack. My key takeaways were the ultra-methodical approach and the strategic and creative reuse of a limited number of pieces. I’m looking forward to trying it on my own for our family trip in June — stay tuned!
Are you all planning your outfits when you pack?
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