REASONS TO BUY
Classy
Stylish look
REASONS TO AVOID
Very expensive
Low capacity
Not versatile
Kenneth Cole Reaction Risky Business Review
This bag is a risky purchase, in our opinion
Kenneth Cole Reaction Risky Business
Credit: www.kennethcole.com
RELATED: Best Messenger Bag of 2023
Our Verdict
While the Kenneth Cole Reaction Risky Business has the best name in this review, that's the only thing it can take top marks for. It's fine for someone who likes the simple and classy look of soft, full-grain leather and who carries light loads on short, straightforward commutes, but it scored below average in our tests and across many of the metrics. It's tricky to properly utilize all the space inside this bag and get the flap to close; unless you have superior Tetris skills, you will likely be frustrated. This is a very classy-looking leather bag, but despite the durability of leather, the rest of the design, straps, and stitching do not inspire much confidence.
Our Analysis and Test Results
The Risky Business is risky indeed, and unfortunately, this pricey bag couldn't withstand our rigorous tests.
Performance Comparison
The Risky Business is expensive and finishes towards the bottom of the fleet, scoring low across our rating metrics.
Credit: Lyra Pierotti
Comfort
The Risky Business gets its few comfort points from the soft and supple leather it's made from. This makes it nice to handle and have hanging around on long days. Although the shoulder padding is small and thin, its stiffness maximizes support for carrying comfort.
The Risky Business messenger bag in action.
Credit: Lyra Pierotti
Packing & Organization
The Risky Business is small and has few organizational options. We went to pack this for a simple weekend workshop — textbook, notebook, pen/pencil, business cards, iPad with cords, chapstick, wallet, phone — and couldn't find room for all of that. We were forced to ditch it for another model that could properly hold our essentials. You can't overstuff this bag because the front flap has to reach a set of magnetic buttons for it to close, and they're not strong enough to pull everything closed like a bag with adjustable buckles or straps. We didn't dislike everything, though. The flat pocket on the back is great for stashing the mail or a handout from a class, and the internal zipper sleeve holds loose papers nicely and keeps them from becoming dog-eared.
We loved the back sleeve for quick access documents and picking up mail, but it wasn't enough to make up for the lack of space on the interior.
Credit: Lyra Pierotti
Electronics
The Risky Business is also risky when it comes to your business essentials. There is no extra padding for a laptop, so be sure to handle this bag with care when your computer is inside. There are no obvious or easy organizational features to keep cords neatly stowed and out of the way. And while the internal zipper compartment is suitable for an iPad or eReader, you can't stash a standard laptop inside —- instead, it must sit loosely in the main compartment. While the bag is compact enough overall that your laptop won't flop around excessively, (especially with another folder, book, or binder inside), it is not optimized for electronics like many of its competitors.
It holds a few slim books and binders well, but not much else. We managed to fit our old 14" laptop, but there is no padding specifically for fragile electronics.
Credit: Lyra Pierotti
Ease of Use
This bag is also not designed for biking. There is no cross-body stabilizer strap, although, for a short ride, it does better than expected. The leather is stickier than the synthetic fabrics of other bags, which helps minimize slippage while riding. Its geometry is also such that it can stretch between your lower back and shoulder, using a little tension to help stay put. The magnetic closure buttons on the front make opening and closing a breeze, and the sleeve on the back is also quite useful. However, without swivels where the shoulder strap attaches to the bag, the strap can easily get twisted. We did not find this to be an issue in our testing, but we hear reports that it can be irritating for some.
The Velcro tab that closed the back flap seemed like it was slapped on as an afterthought, which seems a bit hasty for such a highly priced bag.
Credit: Lyra Pierotti
Wear & Tear
The Risky Business bag faired surprisingly well in our weather tests. It has excellent folding corner flaps that overlap when you close the main compartment; this will keep items inside dry for a time, even if you find yourself in a sudden downpour. However, no surprise, the leather does absorb water and readily shows damage. The magnetic closure buttons also show wear with just moderate use, especially if you are opening and closing the bag frequently.
The Risky Business absorbed water but kept things dry inside so long as it was upright while traveling through the rain (the side flaps are decent, but only for a time). We question the long term wear on the leather if it continues to get wet, and might consider treating the leather for extensive use in rainy climates.
Credit: Lyra Pierotti
Volume to Weight Ratio
At 1.84 pounds, this bag is reasonably lightweight; however, at eight liters, it's also quite small. As such, it did not score well in this metric.
The Risky Business does not have a high capacity.
Credit: Lyra Pierotti
Value
It's one of the most expensive in our review and comes up short in a few ways. Some users online reported receiving damaged, scratched, or otherwise irregular products (due, usually, to the irregular nature of leather). While you might be lucky and find it discounted online, there are better bags for far less money.
Not a lot of organizational features, especially for electronics, cords, and accessories.
Credit: Lyra Pierotti
Conclusion
The Risky Business has a low profile, small size, and easy-to-use magnetic buttons, making it a fine office bag for workday essentials. It will get you through your commute to meetings, and you'll be looking stylish and professional the entire time. If the price is a non-issue and you love the look of the soft, full-grain leather, this bag may suit you. In our tests and across our metrics, however, it did not stand out as one to run out and buy at full price.
The Reaction Risky Business may look nice, but it did not manage to impress our critical testers.
Credit: Lyra Pierotti
—
Penney Garrett & Lyra Pierotti
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