Kenneth Cole Risky Business Messenger Bag Review

Renowned fashion house Kenneth Cole, is famous for bringing comfort and style to design does it again with their casual bag, the Kenneth Cole Risky Business Messenger Bag. Before we start, let’s see why Kenneth Cole designer wear are the best in terms of comfort, style, pricing and durability.


Kenneth Cole Productions was founded in 1982 by no other than Kenneth Cole. He started by showcasing his latest design then, a pair of shoes. In just two days, they had close to forty thousand shoes. From there, the production opened a store and today the company’s retail stores can be found worldwide in over 20 countries. Today, the company is best known for their unique style and sophistication in their collections ranging from clothing, footwear to accessories.

Kenneth Cole Reaction Risky Business Colombian Leather Flapover Cross Body Messenger Bag

The Kenneth Cole Risky Business Messenger Bag is an attractive, stylishly organized casual bag that offers ample space for your belongings as well as comfort. Below we take a closer look at the messenger bag features.

Full-Grain Leather Construction

The Risky Business packs a soft but rich Colombian full-grain leather. Stylishly polished, the bag is very well built guaranteeing you a lifetime service. Professionally stitched, the bag comes with a polyester lining designed to enhance durability as well as improve the casual look of the bag.

Versatile Interior

Kenneth Cole Reaction Messenger Bag side

Designed with the consumer in mind, the Risky Business comes with a fully-lined single Gusset construction complete with a Flap over closure. The main compartment of the bag is simple and large enough to fit a 13-inch Mac or laptop alongside a clipboard and even a book. The main compartment also houses a full-length zipper pocket designed to keep all your smaller necessities close by.

In addition to that, the bag also features two additional front gusseted pockets designed to fit cell phones and a small notebook.

Adjustable Straps

It can be very irritating and uncomfortable at times to have a bag which you can’t adjust the straps according to the weight being carried and comfort. Luckily, Kenneth Cole Production saw this issue and added an adjustable strap. The Risky Business houses a 20 inch leather strap that can be adjusted up to 24 inches allowing you to keep your carrying options open.


Kenneth Cole Reaction Risky Business Colombian Messenger Bag
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    Very portable at only 3-inches wide.
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    Offers a casual look for a medium category messenger bag
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    Features top tier leather that does not bleed.
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    Houses many compartment to help you neatly organize your necessities including inner zipper pockets
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    A 20-inch adjustable and padded shoulder leather strap opens up more carrying options without the expense of comfort or style.
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    Convenient and comfortable to carry handle
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    Available in dark, brown or tan leather


  • Does not offer the conveniences of a laptop bag.
  • May not very convenient when traveling long distances.

My Final Thoughts

For the fair price on Amazon, the Kenneth Cole Risky Business Messenger Bag is a sure steal for many. Designed by one of the best designer companies, this bag leaves no stone unturned when it comes to perfection. I highly recommend the bag to anyone looking for a replacement or a business bag to match that casual look admired by many.

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Kenneth Cole Reaction "Risky Business" Messenger Bag
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