After Traveling 100K Miles This Year, Here’s What I’ve Learned About Packing

When I turned 15, my Aunt Mary gave me my first astrology reading as a birthday gift. What I really wanted was a pair of mustard-yellow corduroy overalls from The Gap, but that’s another story.

I don't remember everything about that first, early foray into nodes, conjunctions, and rising what-nots, but one thing in particular from the reading stuck with me: I would travel a lot. Not just for work, but for life. I needed to travel to feel really alive, alert, and connected to my spirit. Say what you will about astrology, but the reader was right: This year alone, I've logged roughly 100,000 miles in air travel. When I took to adding it up through my frequent-flier app, I will admit I was a little horrified. It may not be much to people with the kind of jobs or lives that require being everywhere all the time, but four times around the globe (again, horrified) seems like a whole lot to me (and probably to my cat).

These days, I travel for global media events, speaking engagements, and, mostly, for fashion shows — which is probably the worst reason to travel. Why? Because you have to PACK for them — one hundred of them — and dinners, press meetings, travel days, and, if I'm lucky, a few workouts, too. Yes, all those outfits with two suitcases. Or just one if you're a real hotshot, like Leandra Medine.

When we pack to go on a trip — better yet, an adventure — we aren’t just doing the practical thing, bringing all the functional stuff we need or should have on the road. We're also telling a story of who we are, or who we really want to be, in 20 pieces or less. Even though I feel like my life is a series of packed and unpacked suitcases, I don’t always get it right. Occasionally, I fail miserably, ending up in a far-off location (Tokyo! Milan!) with a selection of things that don’t speak the language.

But with every new fashion season, when the stakes for 18 killer outfits are absurdly high, I always learn something new. But not as a fashion person; I learn as someone who (finally) likes discovering who she is, what clothes make her feel good about herself, and what she might like to happen as a result of the things she’s packed. This time, I learned eight things that might help you on your journey to self-discovery, too — at least when it comes to packing for it.