Packing Is Honest: Why We Really Overpack
Packing Essentials Series — Part 2
This thought hit me mid-pack — standing over my suitcase, holding an outfit for an event that did not exist.
In Part 1, I told you I’m a recovering overpacker. Today I want to talk about why we overpack in the first place. Because it’s not really about clothes. It’s about honesty.
The “I might” trap
Here’s how it goes. You’re packing, and your brain starts narrating: I might go to dinner. I might do this. I might do that. Ooh, what if there’s a rooftop thing? And suddenly you’re packing for a whole social calendar that nobody sent you an invitation to.
We tell ourselves we’re being prepared. Staying open. But let’s call it what it is: a lot of what we’re packing for is pretend. It’s wishful thinking, folded neatly and taking up a third of the suitcase.
There are only 24 hours in a day
And your vacation is where that math becomes painfully clear.
You do not have time to do everything you want to do — that’s true at home, and it’s somehow more true on a trip. You cannot do 28 things in one day. You are not going to walk the whole city, then shop, then stop here, then go there, then change into look number four for the evening portion. That’s not the truth. Even on my busiest trips, that is almost never the truth for me.
So why did we pack like it was? “I might do this, I might do that” — baby, you’re not doing that stuff. And deep down, we know.
Perfect packing is honest
That’s the whole secret. Packing well isn’t about cubes or rolling techniques or vacuum bags (we’ll get there). Step one is a moment of honesty:
What am I actually doing? What do I have to do? Am I doing breakfasts and dinners out, or am I sleeping in and living my best late-morning life? Catch the vibe of the trip — the people you’re going with, the things you’re actually going to. Pack for that trip. The real one. The one on the agenda.
You only have time for what’s actually on the agenda. Let the suitcase reflect reality, not the fantasy itinerary.
Okay — the special occasion exception
Now, if there IS something genuinely special on the trip — a dinner, a celebration, a moment — and you want options? Fine. One or two options. That’s it. And they still follow the Part 1 rule: anchored around the same shoe and the same accessories.
Because here’s the sneaky part: it’s never just the imaginary outfits. It’s the whole supporting cast — the bag of earrings, the extra perfumes, the backup clutch — all packed in service of events that were never, ever going to happen. You didn’t just invite the pretend outfit. You accessorized it.
You still get wiggle room — just less than you think
Am I saying pack like a robot with zero joy? Absolutely not. Give yourself a little room to decide what you want to wear when you get there — that in-the-moment freedom is part of the fun. It’s just not as extensive as you think it is. A little wiggle room is a couple of flexible pieces. It is not a second wardrobe for your imaginary life.
The honest suitcase
Overpacking isn’t a preparation strategy — it’s optimism with a luggage tag. The trips got so much lighter (literally) when I started packing for the trip I booked instead of the trip I daydreamed.
So before your next trip, ask yourself the honest questions: What am I actually doing? Who am I with? What’s the vibe? Then pack that.
Your turn: what’s the most “I might do this” thing you’ve ever packed and never touched? Mine involved heels. On a beach trip. Again. Confess in the comments — this is a safe space.
Catch Part 1 (my five smart packing choices) if you missed it, and join the Playbook newsletter for the rest of the series.
Work hard. Play harder.
— Cori
