Sprezzatura
What twenty years of travel taught me about packing less, dressing better, and becoming more available to whatever happens next.
Fictional Style Icon: Dickie Greenleafe
Every start of summer I rewatch The Talented Mr. Ripley.
It is just so hot.
I love Dickie Greenleaf’s linen shirts and perfectly short-enough shorts.
I love the Wayfarers.
I love the Italian Riviera and the tiny espresso cups and the smoky clubs and the feeling that everyone is having a fabulously chic life (minus the bit about the sociopath).
Mostly, though, I love how effortless Dickie looks.
Which is funny because if you stop and really look at him, there is quite a lot going on.
Sometimes it’s a blazer, a tie and a fedora with brim that should be too short but isn’t.
Sometimes it’s a camp shirt and perfectly baggy trousers.
Sometimes it’s just a white t-shirt. (In fairness, Jude Law could wear a potato sack in that film and look good.)
The clothes change from scene to scene. The ease doesn’t.
Meanwhile Tom Ripley (ewwww) spends the entire movie trying to become someone.
Dickie never seems to be trying at all.
The internet has spent years trying to solve this mystery. Entire corners of Instagram are devoted to helping us dress like we're spending the summer somewhere along the Mediterranean. There are packing lists, capsule wardrobes, mood boards, and enough striped shirts to outfit a small French navy.
I understand the appeal.
My first trip to Europe was with my mom and my sister to celebrate my mother's sixtieth birthday.
Daytime Chic Tourist Shannon.
Elegant Dinner Shannon.
Possibly-Yacht-Adjacent Shannon.
Nightclub wing-woman to my sister Shannon.
I had shoes for scenarios that never occurred and outfits for events nobody had invited me to.
At some point I became convinced I needed ten pairs of shoes from the Prada outlet, including a set of stilettos despite absolutely no evidence that my itinerary required stilettos.
Then I found myself dragging all of it across the cobblestones of Venice. I remember trying to wrestle that suitcase onto a rocking gondola while Italians floated around me looking impossibly relaxed.
My mother was carrying arugula in her purse because we had run out of room.
My sister looked wicked cool, which was particularly irritating because she’d been the family fashion icon since the eighties, when she somehow managed to make electric blue swap-meet eyeliner work.
I looked ridiculous.
Somewhere between St. Mark's Square and that gondola, I started to suspect that being chic might require fewer moving parts.
More accurately, I had confused options with preparedness.
I’ve thought about that trip often over the years.
Partly because in my memory it was perfect.
Mostly because I miss my Mamma terribly and laugh every time I think about the purse arugula.
A few months ago, while helping my smoke-show husband upgrade his wardrobe, I came across the Italian word sprezzatura.
The term dates back to the Renaissance. Baldassare Castiglione used it to describe the ideal courtier: someone who could dance beautifully, speak intelligently, and navigate complicated social situations while making it all appear effortless.
The most admired form of style was effort that had become invisible.
Five hundred years later, the word has become attached to clothing.
A rolled sleeve that shows just a hint of cuff. A perfectly draped linen shirt. A scarf tied just so.
The clothes get most of the attention. What interests me is the ease.
When I think about the most stylish travelers I know, I rarely think about labels.
I think about the woman who spends her afternoon in a museum instead of hunting for blister plasters at a farmacia.
The family that has been lost, sunburned, overfed, under-hydrated, and somehow still manages to look like they did not sleep in the airport.
The person who stays for another drink, wanders another neighborhood, and never seems burdened by the logistics of getting there.
The less energy I spend managing my clothes, my luggage, and whether I packed the right thing, the more available I become to whatever happens next.
That realization arrived one blister at a time.
The first time I traveled to New York for Apple, I found myself sprinting through Times Square late for the meeting in pouring rain in a pair of gray suede Calvin Klein shoes that I was absolutely certain represented the height of sophistication.
By the time I arrived, I was soaked, breathless, and my heels were hemorrhaging into the back of those shoes.
The shoes eclipsed every other thought.
Not the meeting.
Not the people.
Not the work.
The freaking shoes.
Years later, traveling home from Greece through Istanbul with Wilson, we nearly missed our connection to Los Angeles.
The airline assured us someone would escort us to the gate.
Instead they pointed down a hallway and yelled “Koş!” Run.
Everyone started running. Families were scrambling, kids were being dragged, a woman slipped and slid across the floor.
Most of us looked like we’d just stepped off a Greek island because we had.
I happened to be wearing super cool high-tops, unlike the slippery leather gladiator sandals many people had just purchased in Greece and now were attempting an impromptu track meet in.
Even as a self-proclaimed packing pro though, I often find a fashion item I mentally start making into origami to fit into my carry-on.
A couple of years ago, one of my closest and most stylish friends Ruk and I found ourselves in Santa Fe.
Within twenty-four hours we had become convinced we needed considerably more turquoise in our lives.
Travel does this. Every destination offers a version of itself you can take home.
Sometimes it’s a leather bag from Lucca, or a Liberty of London scarf from a Oxfam shop or a Greek coin medallion on a dainty chain perfect against a tan décolletage.
And, sometimes it’s a vintage coat so aggressively Santa Fe that it works beautifully within a three-mile radius of the Plaza and becomes increasingly difficult to explain anywhere else.
One of the most useful questions I’ve learned to ask while traveling is whether I’m buying something because I love it or because I love where I’m standing—how I feel, who I am with, what adventure I am memorializing.
After enough trips, enough airports, enough blisters, and one truly absurd amount of Prada footwear, I've found myself returning to the same handful of ideas.
These Zara flats have stories. (Paris).
Pack For The Person Who Bought The Ticket
The woman packing for vacation believes she will change multiple times a day to match an outfit to each stop of the itinerary.
The woman on vacation has walked nine miles, jumped in the sea with her kid, had a second Hugo Spritz she wasn’t planning on, and is now wondering whether the restaurant with the three-month wait list takes walk-ins.
I pack for the second woman.
She’s much more fun.
One Thing Should Be Slightly Unexpected
For me, this is usually a shoe.
Leopard Sambas that make any outfit fabulous (shout out to Brooke Baldwin for the pro tip).
Liberty x Adidas sneakers that strangers stop me to ask about.
A massive sheer scarf that can be worn a dozen different ways.
Something that feels like a pop without feeling like a costume.
Build For The Whole Day, Not Outfit Changes
One of the most useful things I’ve learned is to build outfits that can survive multiple versions of a day.
A museum. A longer-than-expected train ride. A detour. A lingering lunch. A hotel bar snack that moves on to dinner.
Clothes that don’t require an intermission.
Clothes that can handle spontaneity.
Clothes that can go from sandy and salty to, “Sure, let’s head straight to dinner.”
Those are the pieces that earn a return ticket.
Pack You’ve Learned to Trust
Over the years I've amassed a handful of pieces that work almost anywhere.
A black linen Gap vest with the deep V that works whether there’s a tank underneath it in broad daylight or absolutely nothing underneath it at midnight.
The Zara jeans with the giant cuff that work with a white button down and preppy loafers or heels and a vintage-inspired rock t-shirt.
The Frank & Eileen linen romper I refused to pay full price for but found several colors on Ebay. (size up)
Cute flats or trainers that don’t scream “I am practical!”
None of these pieces are particularly trendy or aspirational. They’ve simply earned my trust.
Bandanna again FTW. (Croatia)
Field Notes
A few things I stand by:
Black. Mostly black.
Black. Mostly black. White if I'm feeling optimistic. Denim in nearly every form. Very few patterns. The less your clothes argue with one another, the less you have to think about them.
Two pairs of shoes.
Three if I’m feeling reckless.
I adore my Beek sandals which are crafted to last a lifetime and am irrationally devoted to all-white Nike TR-9 Flex trainers I scoop up on Poshmark or Mercari that can survive a workout, a train station, and a happy hour at a rooftop bar without embarrassing me.
Zadig & Voltaire high tops are also a major style win. So many cool options. So many on re-sale. Always killer and comfy.
Denim is Switzerland. It gets along with everyone.
A soft denim shirt. A great pair of jeans. A cropped jacket. A killer denim cape.
Bandanas are wildly underrated.
Hair tie. Neck scarf. Sun protection. Emergency towel. Bag accessory. Find vintage.
Buy the linen before the trip.
Wear it. Wash it. Let it soften.
Wrinkles in linen feels intentional. Most other wrinkles look like crap.
And if you’re spending the summer at home instead of on the Italian Riviera, do yourself a favor and watch The Talented Mr. Ripley.
The clothes are terrific.
I suspect most of us are chasing the ease.
The bag I walked by three days in a row and bought. (Italy)
