Confessions of a Serial Cheater

My love affairs with bags big and small

Even though we feature a lot of people in our How I Pack stories who are carry-on only, I’m so not that person. My husband and I are those people who just like options—he far more than I. He proudly announces that he always packs a tux, because you never know when you might need one. My rule is to always pack a swimsuit (and we’re doing a story on that over on yolojournal.com this Saturday).

Last weekend, we did a story on our site about the carry-on bag that you can get away with calling a purse. You know the kind—they fit over your shoulder, and as you pass the gate agent and flight attendant when you’re boarding, you push it behind your shoulder so they don’t see it—the bag that if someone were to actually weigh it, you might get in trouble. Sound familiar? Because I check, this isn’t usually me, except for quick trips—but Carly and Alex on our team, who are vigilant anti-checkers, are obsessed with the bags that work in this category.

My latest affair

Personally, I’m always in search of the perfect trolley bag. It needs to be my portable desk—I have to get a big envelope that has my laptop, two Smythson diaries, several other pads of paper, and a packet of colored pens along with whatever elixir pouch I’m bringing just in case, a sweater and scarf, and a bottle I can fill with water (you get the idea from the above pic). Over the years, I’ve had relationships with many: I’ve tried (and loved) the Paravel—it was stylish, it was such a nice color, and had a trolley strap; we only broke up because it was too tall to squish down under the seat in front of me. Next came a Ghurka market bag, which I used for forever—it was so voluminous that I could put so many pouches in it plus a sweater and scarf—and it wasn’t too tall. I only broke up with it because it didn’t have a trolley strap and it was always falling off my in-cabin Rimowa. Then I moved onto the Rue de Verneuil, which I love for how lightweight it is, and how voluminous it is (it even made it into our sneaky tote roundup below)—but honestly, given how much I travel with my dog who sheds white hair, it was becoming olive with white.

In rotation clockwise from top left: Yolo x Il Bisonte, Rue de Verneuil, Ghurka

I finally got to make my dream bag with Il Bisonte—we took their Le Laudi bag (straps that fit over the shoulder) and added a trolley strap. It fits a LOT! I love this bag, and everyone I know who has bought it feels the same. But then this weekend, I happened to spot a Porter bag at the Armoury in NYC, and my heart started to race. It was navy nylon, with so many compartments. It held the promise of organization. Matt told me to walk away—I certainly didn’t need it; I am a tote person, not an everything-in-its-different-compartment person. I went home and immediately started Googling it to see if I could find it online. I was obsessed. Matt could see my need/want wasn’t going anywhere, so he went back to the store and got it for me. We’ve really only had one date so far—I packed it to bring to Italy, and this was a very straightforward trip. The second date, when I don’t take a giant suitcase and it has to function as my desk plus accessories and some clothes, will happen next week. Stay tuned for that review. (Note: I couldn’t find it on Armoury’s site, but I could swear I saw several others in store. Alternatively, I found this one here that is the same, just one pouch has a side zipper.)

In the meantime, I wanted to share our Sneaky/Deceptive/Tricky Bag story from this last weekend. For you readers who subscribe to our site’s newsletter, you’ll have seen this already. What you haven’t seen is another addition to it—this Ralph canvas bag in green, which I spotted on the same walk when I found the Porter bag. As you can see, I have a problem—and if you suffer from the same affliction (piles of totes in your closet, unable to stick to one carry-on bag), please share in the comments. I’d like to know I’m not alone.

1. The Rue de Verneuil Traversée is one of Yolanda’s favorite carry-on bags—it has a trolley strap and expands/contracts with snaps. It’s a handbag or a carryall, depending on your needs, and it packs flat and weighs almost nothing. €400 (~$430)
   

2. Passalacqua x Chez Dede Grand Sac – This might feel like a random addition because, yes, it’s hotel merch, but it has the right amount of pockets, a key ring, adjustable leather straps, and when it’s fully stuffed it can carry nearly as much as an Away hardshell case—but you’d never know it! Carly even lived out of it for a week-long trip to Massachusetts this summer (which was part of the inspiration for this story). It doesn’t zip shut if that is important to you. €590 (~$635)
   

3. Paravel Rove Weekender – Their website says it fits 2-3 days of clothes plus a wash-kit and we believe them. It also has a removable shoulder strap, interior and exterior zip pockets, and a trolley sleeve. $370
   

4. “Without fail, I always bring my Perriand Weekend—it’s the perfect carry-on bag for me and with the Stowaway inside, I always have a smaller bag at hand.” —Melissa Morris, founder of Métier $5,250
   

5. LL Bean Boat & Tote with zip top – The price is right, and the travel patina just adds to the character. Bonus: you can throw them in the wash if they get really banged up. $54
   

6. “I usually travel with the Away Weekender on top of the suitcase and bring it empty so I can fill it with souvenirs on my return.” —Margherita Missoni, designer and founder of Maccapani $245
   

7. Béis Ultimate Travel Duffle – For a short trip, you could get away with just this brilliantly designed bag, which opens flat like a suitcase. Inside, it has a large zip section, a PVC-lined pocket for toiletries, a padded laptop sleeve, several magnetic or zip exterior pockets, a key strap and removable card holder, and of course, a trolley pass-through. This video of all its features sold us on it. $118
   

8. “My all-time-go-to luggage when traveling is our large nylon bag, the Nabelle Tote Bag. It’s not huge, but it fits what you need for a few days.” —Maja Dixdotter, creative director of By Malene Birger $400
   

9. “No matter the trip, I will always bring my trusty Rimowa suitcase stacked with my Cesta Canvas Tote on top. I designed this bag to be what I wanted in a carry-on. There is a leather slip pocket for your computer, a big zip pocket for miscellaneous bits and bobs, as well as pockets sized for a phone and for a passport. Plus, it fits perfectly on top of a carry-on roller suitcase.” —Erin Ryder, co-founder of Cesta Collective $750
   

10. Ralph Lauren Bellport Tote – Like the elegant, grown-up cousin of the LL Bean boat and tote, this durable double-lined canvas bag has Italian leather trim, three interior pockets, leather handles and a removable shoulder strap. $598
    

11. Alex Mill Weekend Tote – Expandable snap closures, an interior laptop-sized compartment and zip pocket, and double handles. It comes in really nice washed-canvas colors, and you can get it monogrammed if that’s your thing! $195
    

12. Clare V Le Zip Sac – Looks like a large handbag, but it doubles as a carry-on with a hidden trolley strap, shoulder strap and top handles. $495
    

13. Kule Over the Shoulder Tote and Striped Tote – Our associate editor Carly recently brought the short-handle striped tote on a trip to The Bahamas and it was perfect for the beach, hauling groceries, and sitting flat on top of her suitcase. The colors and stripes are so fun and it’s definitely bigger than the size limit of most airlines (especially on puddle jumpers), but it squished under the seat, and no one said anything. The only downside is that it doesn’t zip, so don’t book an exit row where your stuff might tumble out when you put it in the overhead bin. $198
    

14. The Large Bag from French brand L’Uniform has reinforcement feet to keep it protected on the airplane floor, leather grip handles, and exterior snap pouches. Plus, you can customize and monogram it. We’d trust any capacious bag designed by Jeanne Signoles, who shared her (over)packing secrets with us here. $1,050
    

15. Parker Thatch Jack Bag – The patina on this “broken-in” leather bag is so good, and the designer Irene breaks down just how much it can fit in this video. We’re sold! $898