I used to be the guy at baggage claim watching the empty carousel go around while everyone else walked away with their suitcases. Twice my luggage ended up in cities I was not visiting. After the second time, I decided to learn how to pack a full week into a carry-on. It is not magic. It is rolling.

The roll, not fold, revolution

Folding clothes flat creates creases and wastes space. Rolling each item tightly like a burrito compresses it into a cylinder that fits into gaps you did not know existed. A rolled t-shirt takes up about half the volume of the same shirt folded. Navy sailors have been doing this for decades because footlocker space is limited. If it works on a submarine, it works for a weekend in Chicago.

I roll everything except blazers and structured jackets. Even jeans get rolled. The rolled items stack vertically in the bag like firewood, which also means you can see every item at a glance instead of digging through layers.

Use every cubic inch

Socks go inside shoes. Belts get coiled along the perimeter of the bag against the rigid frame where nothing else fits. Underwear gets rolled into the tiniest possible cylinders and stuffed into the spaces between larger rolls. A packing cube for electronics and chargers prevents the spaghetti tangle that happens when cables roam free.

I also pack a single empty packing cube or compression sack for dirty laundry. By day three, clean clothes volume decreases and dirty clothes volume increases. The dirty cube keeps them from cross-contaminating your clean stuff and compresses down to almost nothing.

The outfit formula

For a week in a carry-on, you need: three bottoms, five tops, one mid-layer, one outer layer, and two pairs of shoes (one worn, one packed). All tops must work with all bottoms. Neutral colors only. Nobody notices you wore the same black jeans three times. They do notice if you are lugging a suitcase the size of a small refrigerator through the airport.

Wear your bulkiest items on the plane: jacket, boots, heavy sweater. The cabin is always cold anyway. You are not wasting bag space and you are comfortable during the flight.

Toiletries that do not get confiscated

TSA’s 3-1-1 rule means liquids must be in 3.4-ounce (100ml) or smaller containers, all fitting in a single quart-size zip bag. I replaced almost everything with solids: shampoo bars, solid conditioner, toothpaste tablets, stick deodorant, solid sunscreen. None of them count as liquids. My toiletries now take up less space than a sandwich and zip through security without a second glance.