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Calpak Vs. Cuyana: Which Cult-Favorite Brand Has The Better Work Bag?

As someone who unsuccessfully carried a canvas tote to the office for years—one that did not fit or organize my belongings—I can say with certainty: A great work bag is a game-changer. The best of these bags keep your things together stylishly so you feel empowered and ready for daily commutes, business travel and everything in between. I recently tried two popular models, Cuyana’s System Tote and Calpak’s Haven Laptop Tote Bag, to determine which one was right for my specific needs and lifestyle. The Haven excelled on longer trips, especially air and train travel, while the System Tote seamlessly fit in with my personal style for easy day-to-day use. But which one is the better work bag overall? Read on to find out.

To evaluate these bags against one another, I carried each for two months on a variety of trips: cross-country flights, hours-long Amtrak rides and shorter subway commutes around New York City. When testing the bags, I paid attention to their capacity and organizational strengths, construction and durability, travel-friendliness, design and versatility. Below, my side-by-side review of the Cuyana System Tote and the Calpak Haven Laptop Tote Bag, including the pros and cons of each and which one I crowned my winner.

Calpak Vs. Cuyana Work Bag Review

Cuyana System Tote

Cuyana System Tote

Dimensions: 10 x 13.25 x 5 inches (13-inch size), 11 x 19 x 5.5 inches (16-inch size) | Material: Pebbled leather, Crocodile leather | Colors: Black, Caramel, Cappuccino, Dark Olive, Stone, Navy, Cherry | Compartments: Main compartment with interior pocket | Closure: Snap buttons | Straps: Two top handles | Warranty: 2 years

Pros

  • Beautiful, sleek design
  • Constructed from durable and high-quality Italian leather
  • Versatile for use as a large purse 
  • Highly customizable, with detachable storage inserts and straps sold separately

Cons

  • Relatively pricey
  • May not work for those who prefer a more structured bag
  • Can’t comfortably accommodate larger laptops
  • Top leather handles can stretch over time, especially after carrying heavier loads

Calpak Haven Laptop Tote Bag

Calpak Haven Laptop Tote Bag

Dimensions: 16  x 12.5 x 5 inches | Material: Polyurethane | Colors: Toffee, Black, Birch, Taupe, Hydrangea, Espresso, Smoke, Forest | Compartments: Main compartment; detachable laptop sleeve with pockets on the exterior and interior | Closure: Magnetic snap button (main cavity), zipper (laptop compartment) | Straps: Two short top handles; removable, extendable carrying strap; luggage trolley sleeve on backside | Warranty: 1 year 

Pros

  • Streamlined design with vegan leather construction
  • Many storage options to effectively organize belongings
  • Luggage trolley sleeve is extremely convenient
  • Detachable strap is wide and comfortable, and can be worn on the shoulder or cross-body
  • Good value for money

Cons

  • PU material can feel stiff and plasticky, and cause the bag to bulge oddly when full
  • Finish on handles can wear over time
  • Size of bag may be too big and bulky for some 

Calpak Vs. Cuyana: Brand Overview

Cuyana is a San Francisco–based luxury brand whose motto is “fewer, better.” It designs essential pieces for the modern woman, including workwear staples, leather bags and pouches and select fashion accessories. Cuyana is committed to responsible consumption and sustainability: According to the brand, its products are constructed with 100% sustainably certified materials; it also purposefully focuses on lower production yields to encourage minimal waste of its items and facilitates a resale program on its website. Though Cuyana carries many leather work bags and even a backpack in its assortment, The System Tote is far and away the company’s best-selling item, and we named it the Best Work Bag For Women Overall in our in-depth tested review.

Calpak is also a California brand—founded in Los Angeles in 1989—that began by offering a small collection of wallets and handbags. Now, it’s a travel-focused company dedicated to crafting well-designed and highly functional luggage and accessories for trips of all kinds. Though they range in size and purpose, all of Calpak’s pieces have a playful, colorful aesthetic and a streamlined look and feel. The Haven Laptop Tote is one of Calpak’s bestsellers, and the most comparable of its offerings to Cuyana’s System Tote in size and shape.


Calpak Vs. Cuyana: Design, Construction And Capacity

The Cuyana System Tote and Calpak Haven Laptop Tote are, of course, both rectangular-shaped work bags with detachable parts, but that’s where the similarities end.

The System Tote is a slouchy bag that comes in two materials (pebbled and crocodile-style leather) and two sizes (13 and 16 inches). It’s got two sloping handles on the top of the bag, a flat bottom and two buttons that snap together to secure the bag closed. On either side of the bag is a small brass D-ring where a longer shoulder strap (both a narrow and wide option are available for purchase) can be attached, as well as two small tabs with buttons where different inserts, like a laptop sleeve or a zippered pouch, can be snapped in to create more storage in the bag. The bag itself comes with one small interior pocket which cannot be removed.

I tried this bag without any of the added accessories, and found that it had more than enough space to fit my laptop sleeve–encased 15-inch Macbook Air, water bottle, iPad, wallet and a couple small snacks within the main cavity, while the pocket easily held my keys, pen, gum, lipstick and hand cream. I could have fit another small makeup pouch, light cardigan or even a thin pair of flip-flops in addition to everything else I carried. The bag remained sleek-looking and sat well when full of my belongings; it was also stylish enough to take to happy hour after leaving the office without screaming “work bag.”

The Haven Laptop Tote, by contrast, is made from a stiffer vegan leather (polyurethane) and is super structured, with a boxy shape that almost resembles a briefcase. Like the Cuyana, it has a flat bottom, but is reinforced with four “feet” that steady it when it’s set down. The Haven tote comes with two short handles at the top of the bag as well as a detachable and adjustable shoulder strap. While the bag does have a magnetic button closure, this is only usable when the included laptop sleeve—which snaps into said buttons—is removed entirely. The laptop sleeve features a zippered closure and has tons of storage pockets both inside and outside of it, creating quite a lot of space to secure your belongings. Some of these pockets are elasticized, so you can store larger or rounder items like ballet flats or a water bottle, and a separate pocket has a zipper closure, too.

Spec for spec, the Calpak is a much larger and heftier bag than the Cuyana and thus can fit a lot more stuff. Along with all of the other items I carried around in the System Tote, I was also able to store a gym outfit and pair of running shoes in the Haven (though, admittedly, the sides of the bag did awkwardly bulge out because it was overfilled). And again, because the bag slightly resembles a briefcase in shape, it’s less versatile to carry around outside of a work context.


Calpak Vs. Cuyana: Travel-Friendliness, Durability And Upkeep

Both of these bags were made to be functional for work commutes and business travel, but during my tests, each had their own benefits and quirks in this regard.

As we’ve talked about, the Calpak Haven Tote is a large and roomy bag with a ton of available storage. Its adjustable carrying strap is long enough to be worn over the shoulder or as a cross-body, but in my experience, the latter method fit slightly awkwardly when the bag was too full or housed heavier items like a full water bottle. That said, the thick width of the strap didn’t cut into my torso or shoulder and supported the weight of the bag’s contents evenly. (I barely used the short handles at the top of the bag, so I can’t really speak to their comfort—but they aren’t long enough to use as a shoulder strap if needed and can only be carried by hand or on the forearm. As such, this may not work well if the bag is full and heavy.)

One big perk of the Calpak’s design is the luggage trolley sleeve on the back, which secures the bag to the telescoping handle of a carry-on by sliding onto it. I found this feature extremely useful when taking it on trains and flights, and it helped immensely to not have to carry a heavy bag on one arm while rolling a bulky suitcase with the other. Speaking of trains and flights, this bag fit in the under-seat area as a personal item on most of the trips I took; on smaller planes, it squeezed in most of the way but not entirely and impinged a bit on my foot space.

Because of its PU construction, the bag is generally quite durable; I haven’t noticed any scratches on its main surface even after shoving it under airplane seats and bumping into turnstiles and walls on the subway. After wearing it for a couple of months, I’ve noticed a bit of wear on the finish of the shoulder strap, but nothing more significant than that. Since the bag is still under Calpak’s one-year warranty for a handful more months, I may likely request a strap replacement if the finish starts peeling off more significantly. Cleaning this bag is a cinch both inside and out; I’ve wiped it down with a slightly wet cloth and gentle dish soap between wearing, and used my vacuum’s hose attachment to get crumbs on the inside.

The Cuyana bag also accompanied me on several trains and flights, and fit neatly under the seat in front of me even when relatively full. Despite being constructed from a soft pebbled leather, the bag has surprisingly remained largely scratch-free, excepting for some small scuffing on the bottom four corners, where I’ve seen a bit of rubbing and wear. This, of course, doesn’t reduce the functionality of the bag, and Cuyana’s two-year warranty may help me alleviate this problem if it continues to deteriorate in the next 20 months.

Carrying the System Tote with its included handles can also be a hit-or-miss experience; if it’s too full or heavy, the bag is hard to hoist comfortably on your shoulder, and sometimes the straps can slip off. I have noticed a bit of stretching on the handles, too, as is pretty typical with leather goods. Purchasing one of Cuyana’s adjustable shoulder straps would be an easy way to remedy both of these issues, though, and I’ll plan to do so for the future. In terms of cleaning, I’ve wiped my System Tote down with a very lightly damp microfiber cloth and that’s served me well so far. Since the bag is so soft and flexible, it’s also easy to turn inside-out to remove crumbs and dust from the interior. Cuyana sells a dedicated leather cleaner and conditioner, which I’ll likely be picking up for longer-term treatments.


Calpak Vs. Cuyana: Final Verdict

After spending a few months with the Cuyana System Tote and Calpak Haven Laptop Tote Bag, I sincerely liked both and believe they each have a place in my work-bag lineup. They have different strengths and purposes—the Calpak for longer trips, especially those involving airplane travel, and the Cuyana for everyday use and shorter commutes.

To summarize: The Calpak is a worthy option for housing all of your needed work items, and then some. It comes at a fairly reasonable price of $180—though, arguably, that might be on the slightly high side for a vegan leather bag—and is a chic and durable product with lots of clever details.

The Cuyana System Tote’s timeless style and flexible design mean that it will be able to live in my wardrobe and support my professional needs for years to come. It’s definitely an investment purchase: $328 for the 13-inch size and $498 for the 16-inch model, excluding inserts and accessories (which start at $68 apiece).

If I had to choose one of the two, based on my lifestyle and the moderate amount I travel for work, it would be the Cuyana tote. But your specific needs and preferences may require otherwise, and you can’t go wrong with either of these well-designed options.


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