I Overpack Every Time. Here Is What I Know Anyway.

Let me tell you what overpacking actually costs you. Not the exorbitant airline fees. Not your time. Not the physical toll that lugging an overpacked bag takes on your back. The cost is more subtle and starts before you ever leave the house. It is the weight of too many decisions before the trip has even begun. The friction of dragging something heavy up a staircase that was built centuries before wheeled luggage existed. The frustration of arriving somewhere beautiful feeling burdened instead of free. No room in your bag for discoveries.

I overpack every time. I am working on it. But over years of leaving Maui for long stretches across multiple countries and cultures, I have developed a philosophy that has made me better at it. Not perfect. Better.

Here is what I know.

Pack for how you want to feel. Not for fashion moments.

This is the whole method and everything else flows from it. Before you pull a single thing from the closet, ask yourself, How do I want to feel when I am in x, y or z? Not, What do I want to look like? Think about how you want to feel. Then make choices that move you toward that feeling. 

For me, the answer is always some version of the same thing. Tailored. Easy. Confident enough to blend in wherever I find myself, without performing belonging. This last distinction matters. There is a big difference between dressing to be seen and dressing to have access. I am always after the latter.

Understand what each city is actually expecting of you

This is where most packing advice fails. You can’t ignore the context and nuances of a two week trip with a single wardrobe. And if your summer looks anything like mine, moving between Milan, Florence, Rome, the south of Italy and New York, you are not packing for one place. You are packing for four completely different cultures and moments. Your bag should be set up to prepare you for them all. 

When I pack, I am after fluency. In Milan, I need to be sharp. Bella figura is the standard. You need to come out in cleaner silhouettes, considered accessories, present a kind of effortless chic, a sense that you put thought into your look without trying too hard. 

In Florence, I am after ease and comfort. I am prioritizing movement. You walk constantly, you wander, you linger. So here, I reach for breathable fabrics, comfortable shoes, dresses that move with me. Florence is romantic and practical simultaneously and your wardrobe should be too.

Rome is more sensual. This is where the gold jewelry comes out, where the evening sandal earns its place, where you lean into that particular confidence of a city that has seen everything and remains unimpressed. I dress for that energy.

Finally, in the south I get to exhale. Most like Maui, I slip on the tried and true cotton dresses. Sandals. Hair up. Sunglasses. Leaning in to the kind of simplicity that only looks effortless because you edited ruthlessly before you packed. This is also, not coincidentally, the dream.

By the time I get back to New York in July, I show up in my city exactly the way it wants me, completely undone and unbothered. Uninterested in impressing anyone, the most stylish people in the city in summer are almost always the least overdone and moving along the pavements to their own beats. Tank tops, easy skirts, throw-on dresses, anything that survives the humidity without standing out too much. You want to blend in here for a myriad of reasons. You do not over-style in New York in July. The city will humble you. You keep it simple. 

Pack by leg, not by category

So I pack by leg of the trip, not by clothing category. Milan gets its own cube. The south gets its own. New York gets another. When the context changes, I pull the right cube and the rest stays untouched. No unpacking and repacking at every stop. No searching at midnight for the one thing I need. The system on the outside mirrors the intention on the inside. One city. One beat. One cube.

The one item that bridges all of it

A light denim shirt. Oversized but not shapeless. Soft drape. Perfectly worn and effortless. I wear it over dresses. I tie it at the waist. I use it as a layer on the plane. It works over a tank top with a skirt in Florence. Or a cool-night cover in New York or when daytime air conditioning at a museum or restaurant is aggressive. This item earns its place in every city, almost every context, and many, many moments between the planned ones. If you pack nothing else on this list, pack this.

The shoe conversation

I love shoes. They are a vice. I love how applying a different shoe to the same foundation, like my old go-to New York City outfit of a good denim jean and white t-shirt, dramatically changes the vibe and look of an outfit and makes it brand new. This is probably why I have a tendency to overpack shoes. I am trying to hold myself accountable.

Four. That is the number. A Birkenstock for the long days navigating cobblestone streets, markets, trains, those moments when comfort is not optional. Bring a sneaker for workouts or hikes. Bring one elevated dinner sandal that is clean and elegant and does not pinch or squeeze or make you suffer. And then pack one optional flat for the days that fall somewhere in between.

That is the system. I am committing to it. You should too.

Leave room

This is the why. The principle that holds all of this advice together. You are not just packing clothes. You are packing and preparing for an imagined life, one that you have not lived yet. And that life will be full of surprises and things that you did not anticipate. Like finding a sweet dress in a small boutique on a street you wandered down without a plan. Or a bottle of wine at a cantina that you know you will never find back home that you bubble wrap and stash in your bag. Or discovering a unique piece of jewelry, probably one of one, from an artisan whose work you had never seen before. Something that you know, when you are choosing it, will remind you of your trip every time you wear it.

You cannot find those things if the bag is already full. So pack for the trip you are actually taking. Edit ruthlessly. Hold the line on the shoes. And leave room for what the trip gives back to you.

That is the whole method. I am still learning it, one departure at a time.

What is the one thing you always overpack? I have a feeling I already know. Tell me anyway.