I’ve been packing my carry-on wrong — here's my new strategy to avoid checking a bag

I might be an expert traveler who has airline elite status and a bucket list with all seven continents checked off, but apparently, I don't know how to pack a carry-on suitcase.

In my defense, I haven't put much effort into learning. I am happier checking a bag, and I like knowing that I can bring everything I want and still have room for souvenirs.

However, certain work trips recently necessitated a carry-on-only approach, so I upgraded to an Away The Bigger Carry-On — my first hard-sided suitcase — and invested in packing cubes. Fitting everything remained a challenge, though.

In desperation, I sought out some advice from my colleague Carly Helfand — TPG's director of content for credit cards and points and miles, and a self-proclaimed carry-on travel expert. She opened my eyes to two key aspects of packing light.

One, I was making bad choices about what to pack.

And two, I was putting those things in the wrong places in my suitcase.

A better approach to travel outfits

I've packed for enough trips to follow all the old adages. Color coordinate clothing so that you can mix and match, and ensure your shoes work with all your outfits. Pack layers to handle changeable temperatures. Bring accessories to change or liven up your look.

I was a dedicated disciple, but I still ended up checking a bag every time.

Carly had two new pieces of advice for me.

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She told me to forget my usual mindset that at the end of the day, most clothes are dirty and must go into the laundry pile. Just wearing a shirt or skirt once doesn't make it dirty if you haven't sweat through it or spilled something on it.

With this altered perspective, I could contemplate wearing a top more than once and reducing the number of jeans or leggings needed for a week away. She also recommended that I look into clothing items that I could dress up or down, further reducing the need for extra outfits.

Her other piece of advice was to prioritize clothes that pack smaller or roll better so you can squish more of them into a carry-on. For example, a swing dress and leggings will take up less space than jeans and a sweater.

I've always been a jeans girl, but I can see how the stiff material is not easily compressible in a carry-on. I scoured my closet, and it was clear I needed to go shopping for more versatile travel clothes. In theory, however, I'm down with this approach.

I put these lessons to the test on my most recent trip: a five-night cruise with a night in a hotel before and after, plus an overnight flight. I packed two pairs of jeans, five tops, one dress, a blazer and a black cardigan. I wore the same dress and leggings on each flight.

I wore the black jeans with the blazer to interview a cruise line executive, and I paired the blazer with blue jeans for a cute yet casual evening look. I wore the dress to two dinners, with and without the cardigan. When I wore jeans and a blouse to dinner, I'd wear the look again the following day.

The lessons I learned from this first attempt will help me streamline further for the next trip. I could have gotten away with one less top since there were two shirts I only wore once. If I'd had a dress that was more of a day-to-night option or a skirt that matched multiple tops, I could have swapped one pair of bulky jeans for a more packable wardrobe choice — freeing up more space, perhaps, for souvenirs.

The right way to pack a carry-on

Carly's second piece of advice was the one that really blew my mind.

My Away carry-on opens down the middle and has two compartments for packing items. One side has a flat bottom and a mesh lining that zips up to keep my belongings from falling out. The other side has a lumpy bottom (due to the suitcase handle track underneath) and a firmer cover with a mesh pocket that I cinch with two straps to keep the items on that side from falling out.

I have always used packing cubes for my clothing when traveling with this Away bag in the past. I fit a medium cube and another small one in the zippered section and my shoes, toiletries and assorted other items in the other half.

According to Carly, I'd had it all backward.

She said I wouldn't need packing cubes if I rolled my clothes and used the cinch straps to compress them tightly into the suitcase. She advised me to pack my shoes and toiletries in the flat, zippered side.

Mind blown.

I followed her advice, and she was 100% correct. By rolling my clothes and fitting them around each other, I could pack my outfits more tightly than I could with the packing cubes, which always rounded in the middle and left gaps between them. Cinching the clothing in with the straps worked better than my regular cubes, which don't specifically compress.

I managed to fit a pair of Rothy's flats and casual sneakers (stuffed with socks, naturally) into the other side, along with toiletries, an umbrella, a foldable duffle bag and a travel purse.

Miraculously, the suitcase closed without me having to sit on it.

I added a laptop bag with my electronics, snacks, water bottle, pashmina wrap, headphones and a clutch purse. I looped my neck pillow to the strap, and then I was all set for a weeklong trip. I didn't need a checked bag, and I had no fear that I had to leave something behind.

Bottom line

I only made one mistake: I rocked up to the TAP Air Portugal counter, blissfully unencumbered by a giant suitcase. When the agent asked if I'd like to check a bag, I proudly answered, "No, I'll be carrying these bags on."

Then he asked to weigh my suitcase.

It was 3 kilograms (6.6 pounds) over the weight limit, and he told me he'd need to check it.

Clearly, I still have more to learn.

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