I Can Pack Weeks of Outfits Into a Carry-On—These Are My Golden Rules

Ever since a two-month solo backpacking trip after my freshman year of university, I’ve conditioned myself to be an ultra-light packer. Something about having to carry all my belongings on my shoulders really taught me the value of bringing a minimal wardrobe on vacation—without sacrificing style, of course.

There are definitely trips (during Fashion Month, for example) where it’s impossible not to pay exorbitant checked bag fees on airlines. But for most travel, I prefer a carry-on or even a travel tote to minimize the amount of stuff I have to lug around—and maximize the chances of my bag actually making it to the destination.

I’m currently on a two-week trip home to Canada to visit my friends and family, and I've realized that I really have perfected my packing routine. It’s methodical, it’s formulaic, and most importantly, it’s not boring.

Pack For the Occasion, Not the What-Ifs

I am a daydreamer to my core, which means I’m often found buying floor-length gowns or opera dresses without truly thinking it through. While this works for home, it does not work for limited luggage space. I always try to be realistic about where I’m going and what I'll be doing.

For this visit home, for example, I had concrete plans that involved a friend’s birthday party and two or three nice dinners out. This meant ensuring I had at least one nice dress I can style up or down, and a nice structured jacket for wearing alone or popping on over looks. I opted for this Vivienne Westwood Red Label piece purchased in Paris last fashion week: it’s a very approachable steel blue and the perfect length. With a ballet flat, it's everyday but for nighttime. I paired it with a pair of leather boots and this heavyweight Damson Madder trench for more drama.

My thrifted Ralph Lauren evening jacket was also an essential I could take downtown and transition into dinner out when paired with the Tory Burch pierced inverted heel. Something about a structured coat with a pair of low-waisted jeans and a fancy shoe screams laid-back but chic to me.

Stick To a Color Palette

If you’re anything like me, your brain is also scratched by a good color combo. My current hyperfixation is purple anything, but especially purple and red. While packing, I subconsciously gravitated towards pieces in this color palette—but when I consciously put together outfits, I realized what a huge favor past me had done for future me. Having a cohesive travel wardrobe doesn’t only mean sticking to black because “it goes with everything.”

Of course I always have a few neutral styling pieces with me. But by bringing this Permanent Vacation top in this perfect grape purple, and my purple $9 tights along with my red ballerinas and red cashmere cardigan, I unlocked a superpower of turning these colors into super-stylable capsule wardrobe essentials. It’s true, black does go with everything, but who knew purple goes with everything too?

Repetition of Tried-and-True Pieces

While it’s true that by the nature of my job I have to think about things like photographing new pieces, and I try to avoid rewearing the same looks too many times, I don’t believe that’s the philosophy to subscribe to if you want to truly reach expert-level packing. For looks that don’t ever see Instagram (but do get mileage in my everyday life), I like to follow a simple rule: If I’ve worn it more than three times this month in my real life, then I’ll probably need to bring it for my vacation life.

For example, I could not stop wearing this Citizen of Humanity Henley under all of my sweaters in New York, so of course I’ll wear it a ton in Canada too. I also thought that this Salter House cotton skirt was a no-brainer. It went with pretty much everything I had in my makeshift closet, and it will probably be reduced to tatters by the end of the season. I had to carefully consider my outerwear options because they take up so much luggage space, but I opted for this wool jacket from Danz that I wore pretty much every day in the city.

We often try to reinvent ourselves for new destinations without considering how emotional dressing really is. Humans crave repetition, comfort, and routine. So why not bring something you’ll actually wear on a trip? We've all returned from a trip with a suitcase of clothes that never got worn, so just be true to yourself and save yourself that mistake.

What I Would Have Brought (or Left Behind) If I Could Re-Do My Trip

I can’t claim to be perfect at packing; I definitely have some regrets now that I’ve gotten a chance to organically wear everything. If I could go back, I would have definitely brought a black shoe, as I only had a brown boot, a red ballet flat, and a burgundy mule to work with. I also underestimated how cold it would be in Vancouver and brought a beautiful, albeit tropical matching silk set that never got worn. But hey, at least hot-weather clothes take up no space once they’re folded! Everything is a learning experience, but having a 90 percent worn rate feels like a success to me.