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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 | $89.99 at Amazon
Pros:  Classy, stylish look
Cons:  Very expensive, low capacity, not versatile
Manufacturer:   Kenneth Cole
By Penney Garrett & Lyra Pierotti  ⋅  Jan 15, 2020
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34
OVERALL
SCORE


RANKED
#13 of 13
  • Comfort - 25% 4
  • Packing & Organization - 25% 2
  • Electronics - 15% 4
  • Ease of Use - 15% 4
  • Wear & Tear - 10% 4
  • Volume to Weight Ratio - 10% 3

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.


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Price $89.99 at Amazon$179.00 at Amazon$64.93 at Amazon
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Pros Classy, stylish lookWaterproof laptop sleeve, weather resistant, easy to use, great features, ambidextrous, brightly colored interiorDurable, comfortable, simple but thoughtful storage, customizableWaterproof, comfortable, lightweight, highly durable, ambidextrous shoulder strapUnique low-profile shape, secure, expanding compression straps accommodate many load sizes, durable
Cons Very expensive, low capacity, not versatileExterior water bottle pocket is small, shoulder padding can get bunched up, tips over easily when set downMinimal features for electronicsTips over easily when set down, doesn't have very many pockets, expensiveFew pockets, not very waterproof, can only be worn on one shoulder
Bottom Line This expensive model didn't live up to its price tag in our tests.This well-featured bag is feature-rich, fully ambidextrous, and highly weatherproof.This tried and true design continues to be one of the best simple messenger bags on the market.With thoughtful features and burly weatherproofing, it's comfortable, lightweight, and ready to be your go-to bag.Deceivingly compact, this mighty sling bag can adapt to many different load sizes and is highly durable.
Rating Categories Reaction Risky Business Timbuk2 Especial Stash Timbuk2 Classic Arc'teryx Granville 10 Chrome Vale Sling 2.0
Comfort (25%)
10
0
4
10
0
7
10
0
8
10
0
9
10
0
8
Packing & Organization (25%)
10
0
2
10
0
8
10
0
7
10
0
5
10
0
6
Electronics (15%)
10
0
4
10
0
9
10
0
5
10
0
7
10
0
6
Ease Of Use (15%)
10
0
4
10
0
7
10
0
8
10
0
7
10
0
7
Wear & Tear (10%)
10
0
4
10
0
9
10
0
8
10
0
9
10
0
7
Volume To Weight Ratio (10%)
10
0
3
10
0
8
10
0
9
10
0
7
10
0
7
Specs Reaction Risky... Timbuk2 Especial... Timbuk2 Classic Arc'teryx... Chrome Vale Sling...
Measured Weight 1.84 lbs 2.18 lbs 2 lbs 1.15 lbs 1.74 lbs
Measured Volume 8 L 20 L 21 L 10 L 14 L
OGL Volume/Weight Ratio 4.35 9.17 10.50 8.70 8.05
Dimensions 16 x 10.5 x 3 in 17.5 x 12.2 x 4.72 in 14.6 x 12.2 x 7.1 in 16 x 10.5 x 5 in 13 x 9.25 x 5 in
Shoulder preference Either Either Either but optimized for left Either Left
Number of Compartments 1 3 2 2 2
Number of Large Pockets 4 5 3 1 3
Number of Small Pockets (i.e. sleeves for pens, thin items) 6 4 5 1 2
Number of Zipper Pockets 1 3 3 2 2
Key Clip? No Yes Yes Yes No
Reflective Material? No Yes Yes, on bottom straps No Yes
External Side Pocket No Yes No No Yes
Sleeve For Laptop? No Yes - 15" Yes - 15" Yes - 12" Yes - 13"
Stabilizing Cross Strap No Yes Yes Yes Yes
Available Sizes One Size One Size XS, S, M, L 10L and 16L One Size
Size Tested One Size One Size Medium 10L One Size

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.
The Risky Business is expensive and finishes towards the bottom of the fleet, scoring low across 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. Although the shoulder padding is small and thin, its stiffness maximizes 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 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.
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.

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.
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.

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.
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.

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.
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.

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.
The Risky Business does not have a high capacity.

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

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.
The Reaction Risky Business may look nice, but it did not manage to impress our critical testers.


Penney Garrett & Lyra Pierotti