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Kenneth Cole Reaction Risky Business Review

This bag is a risky purchase, in our opinion.
Kenneth Cole Reaction Risky Business
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Price:  $300 List | $94.99 at Amazon
Pros:  Classy, slylish look
Cons:  Expensive, low capacity, not versatile
Manufacturer:   Kenneth Cole
By Penney Garrett & Lyra Pierotti  ⋅  Aug 21, 2019
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39
OVERALL
SCORE

RANKED
#8 of 8
  • Comfort - 25% 4
  • Packing & Organization - 25% 2
  • Electronics - 15% 5
  • Ease of Use - 15% 4
  • Wear & Tear - 10% 5
  • Volume to Weight Ratio - 10% 5

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 scored below average in all of our tests, and across almost all of our 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 nearly as much confidence. The Risky Business is best for someone who likes the simple and classy look of soft, full-grain leather and who carries light loads on shorter, more straightforward commutes.


Compare to Similar Products

(change comparison)
 
Awards  Editors' Choice Award  Best Buy Award  
Price $94.99 at Amazon$134.98 at Backcountry$169.00 at REI
Compare at 2 sellers		$80 List$54.98 at Backcountry
Compare at 3 sellers
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Star Rating
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Pros Classy, slylish lookVersatile, durable, stylish, fun to useWaterproof, comfortable, lightweight, highly durable, ambidextrous shoulder strapCompact, lightweight, customization options, simpleDurable, comfortable, simple but thoughtful storage, customizable
Cons Expensive, low capacity, not versatileNot weatherproof, less classic messenger designTips over easily when set down, doesn't have very many pockets, expensiveToo small for large laptops, no padding, must purchase laptop/tablet protection separatelyMinimal features for electronics
Bottom Line This bag is a risky purchase, in our opinion.Transitions seamlessly from backpack to messenger to briefcase.This sleek, comfortable, and lightweight bag is highly durable and weatherproof with minimal yet thoughtful features.This messenger bag is very small and lightweight, and useful for trips with a tablet and a few items.A great messenger bag but has a lot of thoughtful competition in the industry.
Rating Categories Reaction Risky Business Mountain Briefcase Arc'teryx Granville 10 Tom Bihn Daylight Briefcase Timbuk2 Classic
Comfort (25%)
10
0
4
10
0
9
10
0
8
10
0
7
10
0
8
Packing & Organization (25%)
10
0
2
10
0
8
10
0
6
10
0
6
10
0
7
Electronics (15%)
10
0
5
10
0
9
10
0
7
10
0
7
10
0
6
Ease Of Use (15%)
10
0
4
10
0
7
10
0
7
10
0
9
10
0
6
Wear & Tear (10%)
10
0
5
10
0
8
10
0
9
10
0
7
10
0
6
Volume To Weight Ratio (10%)
10
0
5
10
0
6
10
0
8
10
0
8
10
0
7
Specs Reaction Risky... Mountain Briefcase Arc'teryx... Tom Bihn Daylight... Timbuk2 Classic
Measured weight (pounds) 1.84 2.26 1.15 0.99 2.19
Measured volume (L) 8 13 10 8 16
OGL Volume/Weight Ratio 4.34 5.75 8.69 8.1 7.3
Dimensions (inches) 16 x 10.5 x 3 13 x 11 x 4.5 in 16 x 10.5 x 5 14 x 10 x 4 14.6 x 12.2 x 7.1
Shoulder preference Either Either & both w/ backpack straps Either Either Either
Number of Compartments 1 1 1 1 2
Number of Large Pockets 4 1 2 5 6
Number of Small Pockets (i.e. sleeves for pens, thin items) 6 3 0 0 4
Number of Zipper Pockets 1 2 2 3 3
Key Clip? No No Yes Yes Yes
Reflective Material? No No No No No
External Side Pocket No No No No No
Sleeve Fits Laptop No Yes - 15 inch Yes - 12 inch Yes - 13 inch Yes - 15 inch
Stabilizing Cross Strap No No, has backpack straps Yes No Yes
Available Sizes One Size One Size 10L and 16L One Size XS, S, M, L
Size tested One Size One Size 10L One Size Medium

Our Analysis and Test Results

Performance Comparison


The Risky Business messenger bag is the riskiest purchase in our review. It's expensive and finishes in last place after scoring low across all of our rating metrics.
The Risky Business messenger bag is the riskiest purchase in our review. It's expensive and finishes in last place after scoring low across all of our rating metrics.

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. And although the shoulder padding is small and low profile, it is stiff, which allows it to maximize support for carrying comfort.

The Risky Business messenger bag in action.
The Risky Business messenger bag in action.

Packing/Organization


The Risky Business is small 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 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 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.
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.

To be clear, we didn't dislike everything. The flat pocket on the back of this bag 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 getting dog-eared.

Electronics


The Risky Business is indeed a bit 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 overall 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.

The Risky Business messenger bag holds our old 14" laptop but there is no padding specifically for fragile electronics.
The Risky Business messenger bag holds our old 14" laptop, but there is no padding specifically for fragile electronics.

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 contributing to our opinion that this is a hastily made bag for the price.
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.

Wear and 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 show damage readily. The magnetic closure buttons also show wear relatively quickly and 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 (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 Risky Business absorbed water but kept things dry inside 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.

Volume to Weight Ratio


At 1.84 pounds, this bag is reasonably lightweight, but it is also quite small. As such, it did not score well in this metric.

The Risky Business messenger bag does not have a high capacity.
The Risky Business messenger bag does not have a high capacity.

Value


This is a very spendy bag, the most expensive in our review. Our tests showed that it 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 heavily discounted at online retailers, which raises its value somewhat. There are better bags, though, in our opinion.

Not a lot of organizational features especially for electronics cords and accessories.
Not a lot of organizational features, especially for electronics, cords, and accessories.

Conclusion


The Risky Business bag has a low profile, small size, and easy-to-use magnetic buttons, making it a fine office bag for those workday essentials. It will get you through your commute to meetings, looking stylish, and professional the whole time. If the price is a non-issue and you love the look of the soft, full-grain leather, this bag will 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 Risky Business messenger bag holds a few slim books and binders well but not much else.
The Risky Business messenger bag holds a few slim books and binders well, but not much else.


— Penney Garrett & Lyra Pierotti