We are off to Italy!

The first time I visited Italy, I was celebrating my 50th birthday. It was amazing. Now this is my 4th time back in Italy. We're headed to Milan, Lake Como, and Umbria, somewhere I've never been before.

Here's the thing about Italy at the end of September. It's warm in the afternoon, cool at night, and there's always a chance of rain. Milan is a fashion city, Lake Como is a little dressy, and Umbria is cobblestones and countryside. So I needed a wardrobe that could do all three without hauling half my closet across the ocean.

I'm just going to say it: I did not pack in a carry-on. I used to have aspirations to do that, but I've decided not to put that pressure on myself. At the same time, I didn't want to overpack. So I laid out my outfits thoughtfully and tried on everything. Yes, I did throw in a few extra things… just in case.

I'm sharing exactly what I'm wearing on the plane, what's in my carry-on, and how I packed my suitcase. If you've got a fall trip coming up, steal whatever helps.

What I'm Wearing on the Flight

An overnight flight to Europe is not the time for stiff jeans and a tight waistband.

My rule is simple. I want to be comfortable enough to sleep and put together enough to walk into a hotel lobby in Milan without feeling like I rolled out of bed. (Even though I basically will.)

Here's what I'm wearing:

My Vuori set. Pants, a top and a hoodie to layer over both when the plane gets cold. Soft enough to sleep in, put together enough to walk into a hotel lobby in Milan.
Veronica Beard sneakers. Already broken in. Never new shoes on a travel day.
Compression socks. Not glamorous. Completely necessary after 50. My ankles thank me every time.

A little petite tip since I'm 5'2": if the set comes in petite, get the petite. Extra fabric pooling around your ankles is not cute and it's a trip hazard in an airport.

What's in My Carry-On

My carry-on is my insurance policy. If our suitcases decide to take their own vacation, we can survive the first day or two with what's in here.

The bag itself: my Lululemon backpack. It's my personal item on the plane and my everyday bag once we land.

Inside:

My laptop.
Bioactive Peptides and creatine. My daily non-negotiables, even on a plane.
My charger and a Bluetooth adapter.
Noise-canceling headphones. Non-negotiable for a long flight.
My Kindle. Loaded up before we take off. I'm reading Falling for Peachtree Bluff.

You can see my full list of travel must-haves on my Amazon page. It's everything I actually pack, already pulled together in one place.

Then there's the actual carry-on, the one with wheels. That one holds the essentials in case a checked bag goes missing:

A change of clothes for each of us. One for me, one for Jeff. The one thing you don't want to be without if a suitcase goes missing.
Our medications. Never, ever in a checked bag.
My skincare and makeup. Enough to get through a day or two on our own if we had to.

How I Packed My Suitcase

Northern Italy in late September means highs around 70 and nights in the mid 50s. Umbria in early October should be about the same, a little cooler in the hills. So I'm packing for layers, not seasons.

The secret is a tight color palette. I picked navy, cream, camel and black, plus a few stripes because you know I can't help myself. Everything mixes with everything, so ten pieces turn into two weeks of outfits.

I'm also mixing in a few basic tees with everything I'm packing. They layer under the trucker jacket, work on their own with jeans, and I have them in every color, so they earn a spot in this suitcase like they do in every suitcase.

A few pieces work everywhere, no matter which city we're in:

A loungewear set for travel days. This NEGATIVE Underwear hoodie and track pant are what I'll be living in between flights and hotel rooms.
A cashmere tee. This Boden Elsie tee in orange is my one pop of color against all that navy and camel.
A smocked top and skirt set. This Mirth top and skirt in Brownie mix and match with everything else in the suitcase.
A short-sleeve tee. This Vuori Feather tee in ink layers under everything from the trucker jacket to the cardigan.

For Milan (city chic)

Wide-leg pants. These trouser jeans are similar to the ones I'll be taking. Perfect for looking polished and on trend in Milan.
A crisp white shirt. This TWP Next Ex shirt is boxy and easy, tucked in for day and open over a tank at night.
A trucker jacket. This rag & bone Miramar jacket instantly makes any outfit look intentional.
Comfortable ballet flats. Milan is a walking city and I refuse to limp through it, so these M.Gemi Una flats will go with any outfit.

For Lake Como (a little dressy)

A silk midi skirt. This Quince silk maxi skirt packs without wrinkling and dresses up easily for dinner by the water.
An off-the-shoulder sweater. This Ramy Brook Chet sweater pairs with the skirt for something a little dressier.
A cardigan for cool evenings. This Veronica Beard Lira cardigan is for when it gets breezy on the lake at night, perfect for the boat.
A silk hair scarf. These Anthropologie satin scarves tie onto a bag or my hair for something a little extra.

For Umbria (countryside and cobblestones)

Ankle pants for the truffle hunt. These rag & bone Miramar Harlow ankle pants fit like a dream and are perfect for a day of truffle hunting.
A cozy sweater. This Frank & Eileen Mini Cotswolds sweater in camel is perfect for cool mornings and evenings.
Waterproof ankle boots. These Dolce Vita Simaya boots are ready for truffle hunting, and I have a feeling the truffles won't care about my shoes.
A trench coat. This Burberry trench will handle every bit of Umbria's unpredictable weather and packs down small. This piece is an investment, but I've had it for years.

One thing to remember: many churches in Italy ask that shoulders and knees be covered. I'm keeping a scarf similar to this one in my tote so I'm never turned away at the door.

How I packed it all: a few packing cubes, then I rolled and folded things as neatly as possible. I started with my medium suitcase but ended up taking my biggest suitcase. I bought these a couple of years ago and they're perfect for all of my travels.

I have actually decided to take this time off of Instagram to really enjoy my trip. But don't worry, I'll be sharing all about it when I get home, along with all the photos we take along the way.

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What I Packed for Italy: My Real Suitcase