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.
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.
Related reading:
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There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits.Pros
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- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
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| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
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Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits.Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.

