072: Two Weeks in Italy
And all that she wore!
At the end of May, my husband and I headed to Italy for our last trip together before the baby arrives at the end of summer. The plan was to bookend our holiday with a few days in Milan to visit some beloved spaces new and old, and to spend a week in Sorrento, our first time there.
I resist the temptation to label this trip as a “Babymoon” because when we shared with an Italian gentleman that the purpose of our visit was our “babymoon”, he said, slightly scandalized and highly amused, he’d never heard of people traveling specifically to make a baby outside of a honeymoon. We only very narrowly survived dying from total and utter humiliation, me thrusting my belly out to indicate I was very much pregnant already, my husband over-enthusiastically patting my belly to confirm. Just below the surface, we wanted nothing more than to whither away.
A week prior to our departure, I began the holy ritual of packing for a holiday. While I do think of some practical matters, I also take into consideration slightly more frivolously glamorous affairs, like changing into an entirely different outfit for dinner, regardless of where we’ll be dining out. After the long winters weighed down by heavy knits and coats, in the summer I feel lighter, both in terms of what I wear and philosophically. A little zanier, more of that frou frou.
As we were traveling at the tail end of my second trimester, I wanted to not only make sure everything fit well but that they also generous. I tried on every last bit of summer clothing in my closet, pulling out tops and dresses out in front of my ever-growing midsection to see how far they would go, and putting away skirts and trousers that felt remotely like a little squeeze. I struck down my own inclination to pack silly little shoes, and took exactly four pairs that would accommodate my feet in their absolute peak swollen state (glamorous!), good for rain or shine: Tevas masquerading as Prada sandals; a sporty Miu Miu pair which buoyed me through two New York summers; barely-there JW Anderson flats for nice dinners; and espadrilles I bought in Barcelona a few years ago, which came to my rescue after my feet and back could no longer endure the silly little shoes I’d brought for the trip.

On our first full day in Milan, we made our mandatory pilgrimage to Fondazione Prada. After getting dressed that morning, I realized that I had worn a variation of the outfit I wore the last time I was there, about two years ago. I love my Prada but I’ve had to retire most of my pieces for the duration of my pregnancy, and this skirt from the Spring 2012 is one of the few items I can comfortably wear. It also occurred to me that every time I’ve been to the Fondazione, I’ve worn red and white, perhaps unconsciously inspired by Carsten Höller’s Upside Down Mushroom Room.
Later that afternoon, having sufficiently perspired through the above outfit, I changed into a pale mint dress by Sofie D’Hoore I bought to congratulate myself for nearly surviving my first trimester though not quite – after returning from La Garçonne with my new purchase, I was bed-ridden again for three more weeks. I wore this to visit Villa Necchi Campiglio, another of Milan’s cultural institutions I am very inspired by, and then to dinner at Al Matarel. Each time we go to Villa Necchi, my husband and I discover a new detail we hadn’t noticed before; for me it was the Marc Bohan for Christian Dior scarves, and for him, the way all the vents and radiators are elegantly and discreetly disguised. We also got to see the top floor of the Villa, which we never had before, where a selection of architect Piero Portaluppi’s sketches were being exhibited.

The following day we took the train from Milan to Naples, a little over four and a half hours, and then a car from Naples to Sorrento. Coming to the rescue for the long journey were my compression socks, which I find not enough people talk about with regard to maternity style. I would be immobile without them! I first tried Comrad socks, which I found impossible to put on with a bowling ball between me and my feet. Then I thought I’d be very chic and get two different styles from Falke; one had a seam at the top of the toes that became painful as time wore on when I test-drove them, and my thumb went through the second before I could get them on. The best compression socks for me continue to be a hideous flesh-toned pair my father bought for me from CVS several years ago for no particular reason.

My travel outfit to and from Sorrento and back to New York was this Comme des Garçons skirt I bought as a pat on the back for actually surviving my first trimester (I’ve been through a lot, okay!?), a blue Tekla button-down, and a Flore Flore tank top. Paired with the compression socks, I got a glimpse of the eccentric elderly woman I hope to be soon. Comme des Garçons cotton skirts with elastic waistbands and clever drawstrings have been the heroes of my pregnancy wardrobe – they inflect that perfect dash of strangeness I do enjoy when getting dressed.
From morning till swim on most days, I wore a loose navy Loretta Caponi dress with a smocked neckline and cutwork hem. When I first bought this dress a few years ago, there was something about the dress that at times I was unsure of. Even though it was beautiful, it wasn’t the sexiest item, maybe a bit mature. Now, I love the way it falls on my pregnant form. I feel this way about several other items of clothing I own, that they look better now than they once did, which, if anything, makes me wonder whether what has actually changed is how I see myself.
One afternoon we ventured out to have lunch at L’Agrumeto at La Cocumella, where Mary Shelley is know to have stayed, and to wander its beautiful garden. I wore a psychedelic-printed Dries Van Noten dress from the designer’s Spring 2022 collection, ideal for concealing pasta splatters and expansive enough to house my food baby and my baby baby. Another outfit I enjoyed was a silk and crochet lace from Péro with a decade-old skirt. I’ve owned both pieces for the longest time, but it only occurred to me as I was packing to put the two together.
Following a late afternoon shower and nap, I took great pleasure in getting dressed for the evening for nothing in particular. We ate sizable lunches, and spent most of our nights lounging on the hotel terrace watching the sun set, Vesuvius in the distance, snacking on olives and treats while I sipped on my gargantuan virgin Piña Colada (heartburn be damned!).
My embarrassing number of Dries Van Noten dresses have served me incredibly well during my pregnancy, now into my third trimester. I fell madly in love with the black and white dress when I saw it on the runway for Julian Klausner’s first spring undertaking for the brand – very 60s Marimekko – and look forward to wearing it to bits. The pink dress is from the Spring 2018 collection; I had searched for it for several years until I finally found one that was a few sizes up from what I usually wear. When I took it to my usual place for alterations, they weren’t able to take it in all that much and before I could embark on alternative options, fertility treatments took over while my alternations pile grew bigger, and here we are today. Fortuitous timing, really.
Back in Milan, I wore a skirt from the Milanese brand Labo.Art – they make crisp, paper-thin cotton pieces perfect for sweltering summers – and an old Marni top with a fussy ruffle down the front to see my lovely friend Giulia, who incidentally works at Marni. At the store, I bought a bitchy pair of sunglasses I’ve wanted for years, and encountered two elderly women who were quietly but audibly trying to determine whether I was pregnant or wearing a fabulously puffy ensemble. When I decided to no longer keep them guessing, they lavished me with compliments. I think the measure of a great outfit is when our elders are either totally obsessed or totally befuddled by it, or both. I told my husband in a few short years that would be my best friend and I. He agreed.
Another daytime look: a chlorine-blue Super Yaya skirt and Prada frankenshirt. Worn with the slippers, I look a bit like a stoner uncle, in the best possible way. A little less than a year ago, the wonderful Katie, who pens one of my favorite newsletters and who also owns the same skirt, invited me to collaborate with her on the ways we styled our respective pieces for a special dispatch, which included this exact outfit. I was feeling so terribly low that summer, and looking back, it takes my breath away to think how much my life has changed since.
A great joy of mine when putting together an outfit is often dressing for other women, particularly those I know more intimately. How will it appeal to their interests, their moods, their own histories? To see my friend Alessia, owner of the beloved secondhand Mecca Shop the Story, I put together a sleeveless 70s top by way of Miu Miu’s Resort 2015 collection with a white cotton Comme des Garçons skirt. The last time I saw Alessia, I wore a long black Yohji Yamamoto dress – her mother was a former avid collector of Comme and Yohji, and these brands served as a jumping off point for Alessia’s shop. After a long gossip session, she mentioned she had the exact same skirt in blue, but not before chastising me for perusing her racks – stop shopping for yourself, you need to buy things for the baby! She was wearing a pair of very comfortable cream-yellow Jil Sander sandals we both own. Talk about symbiosis!

On our last night in Milan, we had dinner at Da Panciroli, the recently-opened sister of Rovello. We ate beyond our limits and I still insisted on dessert. All in all, it was the perfect final meal. I wore a black and red floral Simone Rocha summer goth set with more than enough room for multiple meals. To dial down any seriousness – because my belly hanging out is so serious – I wore a pair of mismatched shell earrings I bought at a market in Formentera nearly eight years ago. I don’t buy much jewelry, traumatized by my youthful habit of putting on far too much jewelry, but I like to buy a piece when I’m on holiday, nothing flashy or expensive, but something that will remind me of a special moment in my life each time I wear it.
PS Did anyone else cry while the Knicks received their keys to the greatest city in the world?









Stunning looks. And thank you for the compression stockings note! I just had to wear one for a few weeks after a medical procedure, and the beating my poor toes took from it was horrible. I still can't wear closed toed shoes if I'm walking any kind of distance.
I'm so glad you had such a beautiful trip <3