My Hunt for a Work Bag I Can Bike With
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[Editor’s note: After we published this story, the manufacturer of the winning bag incorporated the author’s note for a padded strap. We’ve updated this story to include the latest iteration of the bag.]
I am someone who almost always needs my laptop on my person, so finding awork baghas been an eternal struggle. I’ve always hated wearingbackpacksbecause, as someone of the five-foot-five experience, it makes me look like I’m headed to a 101 class, even if I’m on my way to a very adult, important meeting. The work bag du jour in New York is, of course, thetote bag. It’s the effortless way of signaling to everybody on your subway car that you subscribe to a magazine. But everyone slinging a MacBook Pro into a canvas bag is lying to themselves — those straps can’t support it.
Over years of forcing myself to be a tote-bag person, I’ve developedshoulder issuesthat now require physical therapy. This is especially complicated if you’re a frequent biker like I am — a tote-bag shoulder slip is a genuine safety hazard while cycling — and if you CitiBike, a tote offers very little security for your items if you affix it to the front basket. So like many in this predicament, I found myself sliding back to a backpack, blending in with the hoards of college students and interns. I have long been someone who shoved my bag under my desk the second I arrived at work, desperate to hide the aberration carrying my various gadgets and notebooks. But I was desperate to become a Work-Bag Icon.
The stylish backpacks
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My journey began where so many young gay guys’ journeys do — with theFjällräven Kånken. I loved the way the status-y college-campus backpack unzipped all the way, its low profile, and its relatively slim straps. But I soon realized it was infantilizing when I moved to New York for a real-boy job. It made me look like I hadn’t even taken the SAT yet, and it offered little real support.
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Y-Pack
I then graduated to theTopo Designs Y-Pack,a slightly larger bag with a more adult silhouette. I appreciated the clasp closure, which fended off hypothetical pickpockets on the subway, but the bag was hard to open on the fly. I’d end up whipping it around violently in public or placing it on the floor just to grab what I needed.
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My pendulum then swung toward something more technical: a beast of a (now-discontinued)North Face backpack called the Commuter Pack. It could fit a change of clothes and support a heavy-duty U-lock, and it had tons of internal organization. But it never shrunk down, and when full, it could easily topple a pedestrian if I turned around too quickly. A terrible New York work bag, but still useful for travel and gear-heavy days.
[Editor’s note: The North Face’sBase Camp Daypack, linked here, is the bag most similar to the discontinued Commuter Pack.]
The wide tote bags
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I have enough self-awareness to know that a vertical tote bag could never actually hold my laptop and variouschargers(I have a lot). I desperately tried to make tote bags from Winner in Park Slope andMerci in Pariswork for my needs. While the landscape orientation could technically fit all my items, the thin canvas was weighed down too much, causing the straps to painfully slice into my shoulders. Plus, tote bags are nightmares to put down on the ground, always leaving me at risk of losing things.
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LL Bean Boat and Tote, Open Top
Enter the perennial favorite, theL.L.Bean Boat Tote. I get it. Its thick canvas is robust and can stand up straight on a coffee-shop floor. If you get the longer ones, the straps are as supportive as they get for a tote bag. The personalization options are delightful and cheeky. The optional zip can help protect loose items. But as a social-media professional, my job often requires me to carry a laptop, a camera, and a microphone — all while trying to capture content on the fly. The tote was just too precarious to carry around all day. Plus, it’s too big and stiff to fit in a CitiBike basket and offers zero protection for inclement weather. I love my Boat Tote, but it will be leaving its hook only for park hangs and actual boat days.
The technical tote bags
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As my hunt dragged on, I constantly found myself complimenting stylish work bags in my office. I always fawned over my former co-worker Christina Hong’sEpperson Mountaineering Climb Tote. She very kindly got me one for Christmas one year. I adored this bag. Its square shape had the best of both worlds, the camo print was different for me but somehow fit perfectly, the cinch top protected the bag in the rain and in CitiBike baskets, and the hoops along the front allowed me to affix my keys to the outside, making them easily accessible and keeping them from scratching my various electronics. The original straps the bag came with, however, were thin, too short, and painful. I decided to cut them off and boughtclip-on adjustable strapsthat I clasped onto the top loops. This solution was my best yet. I could lengthen the straps and wear the bag crossbody while biking for extra support. But ultimately, the weight was distributed poorly with my makeshift solution, and the bag ended up causing discomfort.
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I also trieda DSPTCH totewith thelandscape tote insert for organization.The tote itself is spacious and has a nice clasp to close the top, but the insert is ingenious. It gives you a dedicated place to store a laptop in your tote bag and ensures your bag will always stand up straight when you put it down. However, these straps are also a bit thin, and the insert added too much extra weight. I pack enough heavy stuff into my tote that I can’t use any organization tools that add extra weight.
[Editor’s note: The version Zach tried is no longer available, so we’ve linked to DSPTCH’s updated Utility Tote.]
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Here comes the other Strategist holy grail bag: thePatagonia tote Ultralight Tote. This bag is, in theory, a dream. It’s extremely lightweight. The zip top and technical fabric made me feel better about using it in less-than-ideal weather. The ability to transition from tote to backpack made it ideal for times when I took the train one way and bike home. In my years in the tote-bag wilderness, I realized how much I missed pockets and was thrilled to have a place to put my water bottle again. However, this bag’s vertical orientation never sat right with the way I loaded in my items. The tote straps are too short when it’s heavy, and I found myself using it in backpack mode too often. The lack of structure in the bag made it look lumpy, and my water bottle felt out of the flimsy side pockets too many times. Even worse, I felt like a middle-schooler once again. And while the art world has embraced this bag, so has the vest bro. I once got a knowing nod from a man in a Patagonia vest wearing the same bag on the train, and — with all due respect to that community — it sent shivers down my (load-bearing) spine.
The winner
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You’re probably wondering why, along this journey, I never flirted with messenger bags. I did. I searched plenty. I tried onChrome Industriesbags with their heavy-duty clasps. I eyed theBellroy Cinch Messengerand theUniqlo Multi-Pocket bag,ultimately deciding those weren’t big enough to hold my laptop. I never wanted something with a full flap in front — I wanted easy access like a tote bag and something that could be worn crossbody or on one shoulder. For a long time, I eyed theAdsum zip tote. I liked the ability to wear it two ways, but something about it felt a smidge too unstructured.
Then my favorite menswear Substacker,Street Night Live, mentionedColin Meredith’s Static Comp Bagin a post. I scoured the internet for reviews and pictures of the bag, and while I couldn’t find much, I knew this was it. The nylon is thick enough to make me feel safe putting it down on any surface. The dual-zip pockets allow me to have plenty of items grab-and-go accessible. The dual water-bottle pockets are perfect for my Owala and an umbrella. The zipper keeps my items dry and secure — but easy enough to access that, while filming social content, I can grab things one-handed. My only critique is that when the bag is completely stuffed, the strap can sting a little bit. This is likely my fault for overfilling it, but to solve this problem I circled all the way back to my roots and orderedFjällräven straps. I slid one on and it’s completely alleviated any pain.
Thanks to this bag, I have gone from someone longingly looking across my office for the ideal work bag to being the person stopped on my way in, showered in compliments. I love my charcoal bag, but now I’m telling every co-worker who asks about it to get the other color — theone with the amazing orange accents.
Update: After I wrote this story, winning bag designer Colin Meredith reached out to commiserate. “I’m completely with you on the stinging strap issue. The problem has crept up on me on my travels this year,” he wrote via email. “The next version will have a padded strap, similar to the straps you added.” In the words of Anne Hathaway, it came true! In the designer’s SS26 collection, the Static Comp bag has arrived with a padded shoulder strap.
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