The Kenneth Cole Reaction Risky Business has the best name in this review, but that is the only thing it did best here. It scored below average in all of our tests, and across all of our metrics except Ease of Use and Wear and Tear. If it is not too small for your needed items, it is easy to get into with its magnetic snaps. If you have superior Tetris skills, this bag might suit you, because it is tricky to max out the volume and still get those snaps to close the bag. It is a very classy looking leather bag that is durable due to that leather, but the rest of the design, the straps, stitching, etc., did not inspire as much confidence in its durability.
Kenneth Cole Reaction Risky Business Review
This bag is a risky purchase, in our opinion.
Price: $300 List | $79.99 at Amazon
Pros: Classy, slylish look
Cons: Expensive, low capacity, not versatile
Manufacturer: Kenneth Cole
Cons: Expensive, low capacity, not versatile
Manufacturer: Kenneth Cole
By Lyra Pierotti ⋅ Review Editor ⋅ May 26, 2017
RELATED: The Best Messenger Bags of 2018
The Skinny
Compare to Similar Products
Our Analysis and Test Results
Performance Comparison
The riskiest purchase in this review is this bag by Kenneth Cole, which came in last with low scores across all of our scoring metrics.
The Risky Business messenger bag
Comfort
The Risky Business gets its few comfort points from the soft and supple leather it's made of that makes it nice to handle and have hanging around. And although the shoulder padding is small and low profile, it is stiff, which allows it to maximize support and carrying comfort.
The Risky Business messenger bag in action.
This is not an agile bag, but it stays put better than expected for a bag without a cross strap because of the friction of the soft leather. This improves the quality of your commute, whether from the car to the office or through the busy subway.
Packing/Organization
The Risky Business is a small messenger style bag with 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 hold our stuff.
We loved the back sleeve for quick access documents and picking up mail.
We liked the flat pocket on the back of the bag, great for stashing the mail or a few documents. Inside the bag, we liked the internal zipper sleeve — it was too small for a Manila envelope or folder, but it held loose papers and kept them from getting dog-eared.
The Risky Business messenger bag really didn't hold that much in our official Test Load.
In the OGL Volume and Load Tests, we discovered that you couldn't overstuff this bag because the flap must reach the magnetic buttons and they're not strong enough to pull an overstuffed bag closed like an adjustable buckle or compression strap.
Electronics
The Risky Business messenger bag holds our old 14" laptop, but there is no padding specifically for fragile electronics.
The Risky Business is indeed a bit risky for your business essentials. There is no extra padding for your laptop, so be sure to handle this bag with care when your laptop is inside. There are no obvious or easy organization features to keep cords organized and out of the way. And while the internal zipper compartment is suitable for an iPad or tiny laptop, you can't stash a standard laptop inside; instead, it must sit loosely in the main compartment. The bag is small enough overall that it doesn't flop around excessively, especially with another folder, book, or binder inside, but it is not optimized for your electronics.
Not a lot of organizational features, especially for electronics, cords, and accessories.
Ease of Use
On the OGL Ride Test, we discovered that this bag is not designed for biking. There is no cross strap at all, but for a short ride, it does better than expected. The leather is stickier than the synthetic fabrics of other bags, which helped minimize swinging in front while riding. Its geometry is also such that it can stretch between your lower back and shoulder and use a little tension to help it stay put.
The Velcro tab that closed the back flap seemed like it was slapped on as an afterthought, contributing to our opinion that this is a hastily made bag for the price.
The magnetic buttons do make it easy to open and close the flap, so it is quick and easy to slide documents in and go.
The sleeve on the back of the bag is also an excellent feature. It secures with a tab of Velcro and is a great spot to stash the mail or other grab-and-go documents.
Without swivels where the shoulder strap attaches to the bag, the strap can get twisted. We did not find this to be an issue in our testing, but we hear reports that it can be irritating. And last is the off-center briefcase handle on the top of the bag: it makes the bag tip forward when grabbing, which is a bit awkward.
Wear and Tear
In the OGL Weather Test, the Risky Business bag faired surprisingly well. It has excellent folding corner flaps that overlap when you close the main compartment flap and keep the contents dry for a short walk through a sudden downpour.
The Risky Business messenger bag absorbed water but kept things inside dry so long as it was upright while traveling through the rain (it does not have well sealed side flaps). 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.
The leather absorbs water, which is not great for the long-term wear and tear on the leather, but works to keep the contents dry. And the sleeve on the back is open, but since it rests against your back, it is less exposed to rain.
One durability issue is with the magnetic buttons: these see a lot of stress and show wear relatively quickly with moderate use, especially if you are opening and closing this bag frequently.
Volume/Weight Ratio
At 1.84 lbs measured, this bag is fairly lightweight, but it is also quite small. As such, this bag did not score well in the Volume/Weight Ratio metric.
The Risky Business messenger bag does not have a high capacity.
Best Applications
This bag is best for someone who likes the simple and classy look of soft, Columbian full-grain leather and carries light loads to the office on a shorter, more straightforward commute.
Value
At $300 this is a very spendy bag. Our tests showed that this bag comes up short in many ways, and some users online have reported receiving damaged, scratched, or otherwise irregular products (due, to some extent, to the irregular nature of leather). Luckily, this bag is often found at a large discount at online retailers, which raises its value somewhat. There are better bags, though, in our opinion.
Conclusion
The Risky Business messenger bag holds a few slim books and binders well, but not much else.
The Risky Business bag has a low profile, small size, and magnetic buttons that make this a fine office bag for those workday essentials. It will get you through your commute to meetings, looking stylish and pro the whole time. If the price is a non-issue and you love the look of this bag and the soft, full-grain Columbian leather, this bag will suit you. In our tests and across our metrics, this one did not stand out as one to run out and buy at full price.
— Lyra Pierotti
