Packing reliably stresses people out, and almost always, people pack more than they need. Less is more, plus you can buy anything you need in Italy, so don’t worry.
Ideally, you need just a four-wheeled suitcase and a carry-on bag. I have a Calpak backpack with a strap on the back that slides right onto the suitcase handle. It also fits my 16-inch laptop. Any system that is too complicated stresses me out, so I keep my stuff organized while traveling with packing cubes. They let you move from place to place without fully unpacking, and they make it easy to see exactly what you have to work with in your capsule wardrobe. They also prevent me from overpacking by forcing me to look at all my clothes as a system and make sure everything goes together.
Ensure your day bag has ample space for your passport, a phone charger, and sunglasses. You may want to bring a couple of cotton tote bags if you’d like to carry a sketchbook or do any grocery shopping during your trip.
For the women who want a detailed list with links, here we go:
Two to four pairs of cotton or linen pants in neutral colors
Jeans, but not skinny jeans, in the summer. If you’re traveling in a cool season, and you’re a jeans person, bring 2 or 3 pairs
One casual dress
5-8 T-shirts and tank tops (if traveling in winter, substitute T-shirts for simple sweaters). You can get a variety of scoop necks and V-necks. Get them at Uniqlo, J.Crew Factory, AYR, or Perfect White Tee
1 blouse in a print or bright color. This is your going-out shirt. (Remember the aughts, my elder Millennial friends.)
1 blazer or cardigan
1 cotton scarf
1 pair of pajamas, cotton
Bras, panties, of course
1 pair of simple white trainers
1 pair of ballet flats or loafers
Sunglasses
1 white or blue collared shirt
Let’s get more specific:
This dress from Marine Layer. You can roll it up, stuff it into a beach bag, drive a FIAT over it, and it still looks great.
I wear jeans almost every day, and that makes traveling easy. They match with everything, don’t show panty lines, don’t wrinkle, and don’t need to be washed as much. However, if you’re traveling in the hottest months, they’re not ideal, though I find these wide-leg jeans from Kut From the Kloth to be cool and comfortable. Just make sure to size down with this brand. I’m a size 8, but I got these in 6 petite, and they're still a little roomy.
This Frank & Eileen blazer seems wildly expensive for an unlined jacket, but I have done unspeakable things to it over the course of 5 years, and it has retained its shape and looks fantastic with everything. You don’t have to buy this one specifically, but the idea is to bring a casual, versatile jacket that adds a little polish to your lewk while still being low-maintenance.
These shirts from AYR are worth every penny. Button them up, wear them open over a tank top, or use them as beach cover-ups. You can pretty much wear this shirt with a mix of tanks and dresses for your entire trip.
I also love these scoop neck shirts from AYR. The black-and-white striped one has been out of stock forever, but it’s the most useful shirt I own. It’s soft and light and pairs with everything.
Bombas socks. They are just so well-made and give you a little extra cushion for those 20,000-step days.
A toiletries bag with a hook to hang on the back of the bathroom door.
Miracle Balm from Jones Road is indeed a miracle. I travel with the Flushed shade, a tube of their black mascara, and lipstick. I think Korres makes the best lip balm ever.
A Tide pen that’s always in my purse.
Soak for hand-washing undies in the sink.
The Italian Pharmacy
Hyaluronic acid, particularly the French brands. I see a major difference, and I’ve got one of those Anna Magnani faces that has a distinct line and wrinkle that appears instantly for everything I don’t like or find even mildly suspicious.
Note: This is not medical advice, and I’m not a doctor. This is something I personally buy and use. OKI is a popular Italian over-the-counter and prescription painkiller. It contains Ketoprofen lysine salt, an NSAID used across Italy to treat headaches, toothaches, menstrual cramps, joint pain, and sore throats. I’m not a doctor; I’m not giving you medical information. Obviously, check with your doctor, but as a lifelong migraine sufferer, this is like a religious experience. Again, I’m not a doctor, and definitely not your doctor. I’m just sharing my experience, not giving you medical advice.
Pack your toiletries in a bag that can unfold and hang by a hook on the back of the bathroom drawer. Especially in cities, hotel bathrooms can be tiny, and you won’t have to store your things in the bidet if you bring the right stuff.
For the men
Man friends, if you’re actually reading this, my advice is to keep your clothes simple like Stanley Tucci. Cotton pants or jeans, a polo shirt with a collar you can pop if you’re feeling the Italian vibes.
If you want to really look like an Italian man, wear lots of blue, and also blue on blue. Again, no one nails it quite like Stanley.
And finally, the Italian word for a blow-out is piega. Want to get your roots done? The term is la ricrescita.
