How to Pack a Hawaiian Shirt and Shorts Set for a Trip

A flower-print shirt and matching shorts are one of the easiest outfits to ruin before you even leave the house. Fold the shirt the way you fold a dress shirt, shove the shorts into the bottom of the bag, and by the time you land, one piece looks like a crumpled napkin and the other is hiding under your shoes. Then you spend your first afternoon at the hotel trying to fix a vacation outfit with a sad little travel iron. My husband Kimo wears the COOFANDY two-piece set on trips, and I have packed it for him enough times to know the difference between arriving ready and arriving rumpled.

Kimo is sixty-three, not the fussy type, but he likes to look decent in family photos and he wants a shirt that breathes in warm weather. The set is a flower-print short-sleeve button-down shirt plus matching shorts with an elastic drawstring waist and pockets. It is what he reaches for when the suitcase comes out. The trouble with any matching set is that the two pieces have to travel together and arrive looking like they belong to each other, and they will not do that on their own. So here is the five-step way I pack it, the same steps I use every time we fly out for a family visit.

The other reason I like packing a set instead of separate pieces is simpler than any folding trick: no decisions. Kimo can stand in front of the closet at six in the morning, pull out one roll, and everything matches. No wondering whether this shirt goes with those shorts, no second outfit stuffed in the bag just in case. The print does the work, and the shirt and shorts were made for each other, so they look right together even after a long flight. It also saves space, because two pieces that were made to go together roll into one package instead of two.

Step 1: Wash it on cold and line dry it a day before

A clean set packs better than one you just wore, because the fabric is relaxed and the shirt is not holding yesterday's shape. I wash Kimo's set in the regular machine on cold and the gentle cycle, then hang it on the lanai to dry. Hilo is warm and rainy, so line drying is usually done by the next morning. The set is lightweight and dries fast, which is half the reason it is the one that goes on trips.

Before it goes in the washer, check the pockets. The shorts have them, and loose change or an old boarding pass can leave a lump that presses a crease into the fabric. Check the buttons, too. A missing button on a matching set is harder to fix than on a regular shirt, because you want the spare to match. Fix anything before the wash, not the night before you fly, when you are tired and the stores are closed.

And give the set until the next morning to dry. Line dried clothes have a fresh smell that a dryer cannot copy, and the fabric stays softer. If you are packing in the morning, wash it the day before, not the night before. Lightweight fabric dries quickly, but it dries evenly only if you give it time to hang without being rushed.

Step 2: Button the shirt and lay it out flat

The single best thing I learned is to button the shirt before folding it. A buttoned shirt folds into a flat, tidy rectangle, while an unbuttoned one bunches around the collar and the front placket. Lay it face down on the bed, smooth the back with your hands, and fold the sleeves in so they lie flat against the body. Smooth the flower print as you go, because a print that is bunched in the suitcase is a print that looks wrinkled in photos.

Poi, our little rescue dog, always supervises this part from the foot of the bed, and honestly, the slow version takes less time than it sounds. Maybe ninety seconds once you have done it a few times. The point is to keep the front of the shirt smooth, because the front is what shows in every picture. The back can forgive a little. The front cannot.

I have tried the other way, folding it like a dress shirt with the sleeves crossed behind the back, and it always ends up with a crease down the middle of the print. Rolling is kinder to lightweight fabric, but you can only roll a shirt that has been buttoned and smoothed first. Skip that step and the roll comes out lopsided, with the collar folded over on itself. I learned that on a trip where Kimo's collar came out bent like a taco, and he wore it that way to dinner because we were already late.

Step 3: Fold the shorts and roll the set together

Fold the shorts in half along the legs, then lay them across the middle of the shirt. Roll the whole thing from the bottom up, keeping it tight and even, until you have one neat cylinder of shirt and shorts together. Rolling them as one piece is what keeps the set from separating. You never have to dig through the bag asking where the matching shorts went.

The elastic waistband rolls small and the fabric is light, so the finished roll is about the size of a rolled beach towel, maybe smaller. If you have a packing cube, tuck the roll inside. If you do not, a clean plastic bag from the kitchen drawer works fine. The point is to keep the roll from coming undone and to keep the two pieces married to each other until you reach the hotel.

Do not roll it too tight. A tight roll presses creases into the fabric just like folding does. You want firm and even, the way you would roll a sleeping bag, not the way you would wring out a dish towel. When you get it right, the set sits in the bag like a small, neat package that takes up less space than the pair of shoes you packed under it.

Step 4: Pack it on top, never under the shoes

Where the roll sits in the bag matters almost as much as how you rolled it. Put the heavy things at the bottom: shoes, toiletry bag, the book I always say I will read on the plane. Then lay the rolled set on top, where it will not get crushed. If you are using a packing cube, stand it upright against the back of the carry-on so the weight of everything else presses against the cube, not the fabric.

I pack Kimo's COOFANDY set at the very top of his carry-on, on top of his other shirts, because the last thing in is the first thing out. When we land, he can pull the roll out, shake it, and hang it up before he even opens his toiletries. There is nothing worse than unpacking half the bag to find the one outfit you wanted first.

If you are checking a bag instead of carrying one on, wrap the roll in a clean plastic bag and tuck it between two soft things, like a sweater and a jacket. A checked bag gets tossed around, and the plastic bag keeps the set clean and keeps it from picking up the smell of whatever is next to it. Carry-on is better if you can manage it, but the roll travels fine either way.

Step 5: Hang it in the bathroom and let the steam do the work

No matter how careful you are, a flight will put a few soft wrinkles in lightweight fabric. The fix does not require an iron. Hang the shirt and the shorts on the shower rod, close the bathroom door, and run the shower hot for a few minutes. The steam relaxes the wrinkles while you do something else. By the time Kimo is ready for dinner, the set looks like it came out of a garment bag.

I have used this in hotel rooms and in a beach rental where the only hangers were wire ones. It works every time. If you are in a hurry, run the shower while you unpack, then button the shirt and hang it in the room to finish settling. The COOFANDY fabric is forgiving, which is exactly what you want in a vacation outfit.

Hang the shorts on the same rod, but do not hang them from the elastic waistband with a hanger clip, because that can stretch the band. Drape them over the rod or over a hanger the way you would hang them at home. Steam reaches both pieces the same way, and by morning, even the collar has settled back into its proper shape. If the bathroom is too small to close the door properly, even a few minutes of steam while you take your morning shower will help.

What Else Helps

A few small things make the whole process easier. A packing cube is worth the space it takes in your bag, because it keeps the roll from unrolling and keeps the set together on the way home, when you are tired and less careful. I also keep one clean plastic bag folded flat in the bottom of the suitcase. It does double duty: wrap the rolled set in it if you are checking a bag, or use it for wet swim trunks on the way back.

Choose the day you wear the set with a little thought. Matching outfits photograph well, so I pack Kimo's set for the day we know pictures will happen, like a family dinner or a holiday gathering with the grandkids. If you wear it on the plane instead, you will still look fine, but the print will be at its sharpest on the day you planned it for. Either way, keep the roll where you can reach it, because the set is the easiest thing in the bag to put on.

When you pack for the flight home, roll the set the same way, but make sure it is completely dry first. A damp shirt is the one thing that will not survive the trip home. If it is still damp from the beach or a swim, hang it in the bathroom overnight or drape it over the back of a chair. Hilo has taught me that rushing damp clothes into a bag is how things come home smelling musty. A dry set rolls tighter, too, so you are not fighting the fabric when you are packing at the end of a trip.

And one more thing. Do not leave the set folded in a plastic bag between trips; let it breathe on a hanger. Plastic holds moisture and presses the wrinkles back in. Hang it on a plain hanger in the closet, the way I hang Kimo's set at home, and it will stay ready for the next trip.

The first time I packed this set the slow way, Kimo hung it up at the hotel and asked if I had ironed it. I had not. The bathroom steam did it.