What to wear where

Carry-on only, forever

Just a heads up: I’m OOO next week, so there will be no newsletter.

You won’t be surprised to learn that I’m a staunch carry-on girl. It physically pains me when I have to check a bag. I’ve rarely caved and checked—usually only so I can bring home something worth it like a huge bottle of mezcal on the way back from Oaxaca. And I am convinced that I can travel for up to 3 weeks in a carry-on alone, assuming I’m not going to the snow. That’s probably more like 1.5-2 weeks… Listen, I have no doubt I’m making it harder on myself, but boy oh boy the bragging rights. (And also the thing where you leave the airport immediately after getting off the plane and where your bag isn’t the size of your whole body, etc, etc.)

Two weeks in a little wheelie! Start ‘em young.

I’ve sent lots of new clients on fun trips this summer and many have asked for packing help. So, let’s talk about it! I am not going to give you a look at what I’m packing for my son and I for our trip to England this week (!); not going to espouse some packing cube that changed my life or whatever. Instead, I thought I’d share some things that I’ve learned through trial and error, some fun ideas of what to wear, and then links to great bags and suitcases.

Relevant side note: I got to work with People Magazine again on an air travel etiquette story! Take a look and agree with me!

Packing tips:

Take that outfit out. You know which one I’m talking about. The one you’re probably not going to finally bust out on this trip. Bring one element of it—the funky accessory, that colorful top. But leave the rest and try it again when you’re back.

Minimize your toiletries and gear. Hair tools alone take up so much room. Bring one tool that does a lot. For me, that’s a flat iron. Unless you’re going to a black tie destination wedding for which there are many events, you don’t need it all. Literally zero people at dinner in Barcelona care about how you’ve curled your hair.

Three pairs of shoes. That’s all you get. They have to go with a lot. But more than three, unless you’re en route to the red carpet of the Cannes Film Festival, is only adding weight and taking up space. My go-to for a city trip is a pair of ballet flats and/or sandals, a pair of sneakers, and one versatile pair of heels. For a more countryside / active trip, I’d say two sneakers and one nicer pair of flats.

(Fun fact: I actually did a series of stories just like this for Fodors.com way back in the day and it was consistently our most read series. *Brushes shoulders off.*)