the strategist hunt

I Stopped Strangers on the Subway to Find a Perfect Work Tote

I’ve been on a mission to find one for the past six years.

Photo: Mya Gelber
Photo: Mya Gelber

The other day, I slipped on my commuter shoes (they’re these if you’re curious), hopped on the northbound 4 train, and went to work. And by work, I mean following the 2.4 million people who commute each day by subway to find the perfect work tote bag. Since my first job out of college, I have been searching for that impeccable professional tote bag that would announce: “Here I am, a young professional woman ready to climb the corporate ladder and take on the world!” Six years later, I’m a little less naïve, but I still have yet to find this perfect work bag.

I think my lack of success in the bag department stems from my unreasonably high expectations for my dream work bag. My thought is: This is a bag I have to use every day; I want to love it. However, I tend to find most if not all work tote bags dull, sterile, and devoid of character. Whenever I try to resume this tote-bag search and Google “work tote bag,” the same disappointing results show up on my screen. A hundred different squarish, stiff leather bags with zero personality.

Perhaps I was being unreasonable in my expectations, but I was sure there must exist a bag that could both be the functional workhorse I need it to be and have some visual charm. So I ventured out into the world to find some inspiration. I spotted over 100 tote bags and talked to about 20 tote owners. After risking life and limb to bother New Yorkers at 8:30 a.m. on Monday morning, I bring to you some top tote-bag picks — and the one I ended up buying.

One of the first people I spoke to was Rachell, a radiology student who loves her black Longchamp Le Pliage. I own one too, and it is a fantastic bag; it’s extremely lightweight, and the leather straps are comfortable and stay on my shoulder even when I’m wearing my puffer coat. Rachell’s had hers for three years and owns it in multiple colors.

I noticed quite a few people were carrying around the Baggu Nylon Shoulder Bag, including Marissa Acosta, an education student and barista. “It’s the first tote bag I’ve found that can hold a lot — my laptop, books — without straining my shoulder since the shoulder strap has great support,” she told me. She also appreciates that the bag has a small pocket inside to hold her AirPods and “countless” lip balms. Plus, it’s waterproof.

Amid a sea of solid-colored bags, this striped nylon tote bag by Isabel Marant caught my eye. Brandi, a teacher, told me she loves this tote because it’s so lightweight, especially compared to leather. “I don’t feel like I have the world on my shoulders,” she says. She also really appreciates the two secret pockets and the ever-important inside pocket that zips.

While a nylon bag does make a lot of sense, there is something chic about a great leather bag. Ashley Harris, founder and creative director of the jewelry brand Don’t Let Disco, almost stopped me in my tracks when I saw her stunning cognac leather tote bag, which she’d bought on Etsy. “It’s deep yet surprisingly chic — nobody notices I’m carrying thousands of hand-strung beads inside.” Plus, she said, “it has two internal pockets that introduce a level of organization, and its long straps make it comfortable to wear over even the thickest winter coats, leaving my hands free.” Ashley, who’s leather-bag obsessed herself, assured me there is no worry of dye transfer despite the price and that this kind of leather should develop a perfect patina over time. “This bag is definitely here for the long journey,” she said.

Arguably, the bucket bag is a member of the tote-bag family, and therefore I considered it in my search. Two caught my eye on my journey, the first being the Madewell Essential Bucket Tote. Arianna Paranzino, a marketing director, told me she chose it because it fits her laptop and the strap is the perfect length.

For a softer and slouchier version, the J.Crew Berkeley Bucket Bag looks a little like the ones The Row and Khaite are selling these days without the $2,000 price tags. Marisa Rodriguez, a student, told me she had been looking everywhere for a brown suede everyday bag and was deciding between the J. Crew bag and the Reformation Vittoria Tote Bag. Ultimately she went with the J.Crew, and she loves its versatility. While it’s surprisingly slim, on the day I stopped her she was carrying her lunch, an umbrella, a laptop, and her iPad in it. She’s even used it to carry her tennis racket!

Kayra Oguz, a chemical and biomolecular engineering student, told me that she found this Coach bag after looking for something durable enough to withstand city life. The Coach Lana bag is her current go-to work bag (though it’s no longer available in green). She keeps her lip glosses and her calculator in a center zipped pocket that separates her various electronic devices from her textbooks in the larger compartment.

But of all the bags that I spotted, there was one that stood out from the pack: the Cuyana. I stopped to talk to multiple people with this bag, including Liz Goldberg, manager of global licensing and partnerships at the Met. She told me how she had been looking for the perfect work tote since the start of her career; she purchased dozens and returned most. She was never happy with a tote bag until she found this one. Liz was set on finding a bag that was lightweight but still sturdy enough to hold its shape. The Cuyana tote fit the bill. She loves how the bag is made with soft leather, and even when it’s packed with heavy items, it still feels balanced.

“It’s definitely more expensive than any of my previous tote bags, but after all the money I’ve wasted on ones I didn’t like, and how long I expect this one to last, it’s worth it,” she told me. “I also got an email from the brand announcing a rare sale on the tote the same day I got the offer letter for my current job, which seemed serendipitous.”

The one I bought! Photo: Mya Gelber

I had to see for myself, so I ventured to Cuyana’s flagship store in Soho and tested a few of its work totes. I tested both the Classic Easy Zipper Tote and the Classic Easy Tote. Both bags come in three different sizes and nine different colorways. Each bag can be paired with an insert to create additional compartments or a wide strap to function as a travel bag. I ended up buying the Zipper Tote. The leather really is so soft, and it sits comfortably on my shoulder, even while carrying my thousand-page textbooks. I look forward to seeing how this tote molds to my needs with time. I’ve also preemptively ordered the long strap attachment so I can test it out as a travel bag during an upcoming trip.

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I Stopped Strangers on the Subway to Find a Perfect Tote