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on April 11, 2010
I searched high and low for in-depth reviews on this product, and came up short, so here you are:

Purchased: Dark Brown Kenneth Cole Reaction Messenger Bag

Full Description (What you can't see from the pictures):
- 13 inch width, 3 inch thickness (small-medium bag)
- Single gusset interior pocket, 2.5 inches
- 2 pockets on front of bag containing:
- -Left Pocket: Phone Holder (Blackberry-Tour sized with space)
-Right Pocket: 3 business card/credit card slots, 2 pen holders.
- Interior zipper pocket roughly 10 inches across.
- Back magazine pocket sitting directly behind handle, lined with same material as the interior.
- Strap pattern leading down both sides of the bag.

- The bag pulls off what very few male (or androgynous, as this bag is in the small-medium category) messenger bags can do: it looks great when you're wearing sweatpants or when you're wearing a business suit. The brown is dark enough to seem professional, light enough to go with a black suit (just don't carry it all around with you during a banquet; it's not a man-purse), and has a simplistic enough stitch to come off youthful and assertive.
- The dark brown does not run at all. My guess is that most of the bags that have an issue with the leather bleeding are black.
- It is very portable in comparison to many male messenger bags. At only 3 inches in thickness, it doesn't seem you are carrying your entire life with you.
- Currently my bag is holding my 10" Asus netbook, a 600-page softback textbook, a clipboard, a 20 ounce Coca-Cola, my blackberry, 2 pens, wallet, optical mouse, and keys. The front pockets still have some room for probably a one-subject notebook, a magazine or two in the exterior pocket, and my laptop charger and portable phone charger in the front pockets. This would be the full capacity of the bag, though.
- the leather strap already comes at an excellent size for a 5'10" to 6'0" man, and can be adjusted for several sizes. The shoulder pad is pretty comfortable, fits well with the bag, and stays still when you want it but can be slid to the position you want.
- the magazine pocket is big and has its own magnetic closer. You won't want to put anything other than large magazines or flat objects or it will dig into your thigh.

- The bag is a soft bag, and the leather cover folds in unusual places when being worn or hung up. This will eventually leave marks in the top on the leather. It won't diminish the overall professionalism of the bag, but can be annoying to OCD users who insist on the bag keeping form or folding right at the center.
- The cover stays closed magnetically, and the magnets aren't all that strong. I have lifted the bag by the handle successfully (while the bag is very full) without the covers sliding open, but if the cover is already open, the bag could fold over and let objects in the gusset slide around.
- The strap looks professional but feels awkward when picking the bag up. The bag tips slightly forward when you grab it. I like the positioning because your eyes aren't drawn to the handle when you see the bag, but for those who like a briefcase-style open, it can be a problem.
- The strap must be put on the right side, or else your neck will feel the strain. This is slightly annoying for people like me who like to grab their back while walking and throw it on.
- This bag will take damage. The wear is very natural and still looks professional (it is leather, after all), but marks will become noticeable eventually over time.
- This is most definitely not cushioned for your laptop, nor will it fit a standard laptop above 13" (and 13" is a stretch).
- It is not designed to carry your life when traveling.
- It is a high-volume bag, meaning you may run into others with the same bag even in your own company.

Why 5 Stars?
- It is incredibly multi-purpose for the business user. Any efficient businessperson has made the move to the comfort and portability of the netbook/smartphone combo. It still works for a student, as well, although don't expect it to hold your netbook and several classes worth of books at once. I am a Graduate student who works full time, and it's very nice to go from class, make a quick pit stop to drop off my books and fill it with business work, a drink, and some snacks, and go straight to work.
- Not only does it fit the usability criteria, it also fits the fashion criteria. Nobody, man or woman, will look bad wearing this bag (until they treat it as a man-purse).
- Not only does it fit the criteria to make it look like a Man's messenger bag, it is small and does a LOT with the space it has. A normal Man's messenger bag is 1-2" thicker.
- Every con of the bag does not take away from the versatility or fashion of the bag. They are minor nuisances that take a few minutes to figure out and adjust to, and in only a few days they had become natural for me.
- All together, this bag is more impressive and better looking than many bags several hundred dollars more expensive. If this bag cost $400, it would earn a lower star rating, but it's very similar quality (minus obvious finishing touches of lavish bags) for 75% off the price.
2828 comments|722 people found this helpful. Was this review helpful to you?YesNoReport abuse
on September 30, 2012
I purchased this a month back online over two other bags I was looking at; the higher end Coach 70313 Thompson Slim Messenger and the slightly cheaper eBag's Colombian Leather Messenger. With the Risky Business my initial concerns from looking at the online pictures were the cloth fabric strap being cheap, the magnetic closure snaps not working, and the quality/durability of the leather overtime.

However, regardless of my concerns I was surprised that the Risky Business has the MOST buyer reviews online and the MOST positive 5 stars reviews online of any messenger bag. It is like buyers were so impressed that even the non-reviewers that never return to write reviews had to say something. So I went ahead to see what all the buzz is about.

There are a billion positive things that could be said and has been said about this bag so for sake of brevity I will discuss the Risky Business from the perspective of my three initial concerns and how those concerns turned out to be big positives:

The Strap:
The cloth strap is actually a durable canvas cotton blended with some sort poly-nylon weave that makes the strap feel secure and comfortable. I also own a Tumi T-Tech Houston Portfolio Computer Bag w/ a ballistic-nylon strap and a Filson #256 Original Twill Brief w/ a leather strap and the Risky Business has by far the best strap for comfort, wear-ability and load stability. It is just the right width that the load is stabilized when worn over one shoulder or across the chest. Also the strap extends down the sides and underside of the bag wrapping around the interior load so the burden is evenly distributed around the bag and onto the strap. I don't know who came up with this idea but it is sheer brilliance.

The Magnetic Clasp:
When the flap is put down the little dots magically line up and click-close every time. Accessing the bag is easy since there is no zips to undo each time you want to change a track on your iPod. When the bag isn't overstuffed the flap stays shut during wear. The magnetic dots while obviously not strong at all basically ONLY serves to hold the flap in place (it keeps it from sliding around). It is NOT meant for 'locking down' the bag so if you are Spider-Man and that is something you need then look elsewhere. Non Superheros will be happy with the magnet dots. That said, the main pocket and two front pockets are deep enough and the leather is firm enough that nothing will slide out or ride up and out of the bag. It is true that if the bag is stuffed to the brim the flap will not reach down far enough to the magnetic dots. So to say the flap is unsecured when the bag is stuffed is also saying you are not supposed to stuff the bag to begin with.

The Leather Quality:
Real leather that is rich and desirable is not perfectly smooth, shiny and clean. It should have a rugged distressed, pitted appearance to it and it should smell like leather instead of chemicals. The risky business meets all the requirements of real leather that is rich and desirable. The online pictures may make it look like smooth patent, fake leather but when you unbox it the bag will be leather. I know there have been a lot of complaints, in fact the only complaints I've read, that bags arrived scratched up, pitted, creased and distressed when unboxed. Well guess what people?! real leather isn't made in a computer machine that prints out perfect sheets of it. It is stripped off an animal and cured and processed and dyed and it goes thru a myriad of complex processes before it is tailored to the end product, made into a sweet messenger bag and shipped off to you. That said, the leather quality is top notch to the point that it has a hand-made feel to it which I love. In a month of using my bag to carry books, a Thinkpad T61, an iPad, Groceries, mail-parcels, wet umbrellas, etc... thru the gritty environs of the NYC Subway system the leather and the bag still looks brand new. I also did not have any issues with the brown dye rubbing off.

POSITIVES: Great bag for the price. It is very light weight for a leather bag. There are lots of 'useful' interior space for everyday basic use. In 2012 with Tablets, Smartphones and iPads outselling slow bulky notebooks computers normal commuters and internet cafe slackers no longer carry around the big laptops. So lack of space is not a negative. The cloth fabric strap due to design and weaving outperform bags costing twice as much in categories of comfort and durability. Not making the straps leather also makes the bag much lighter.

NEGATIVES: I'm not a fan of leather piping trim and this bag has it. Piping was big in the 1970s on my granddaddy's car seats and my grandmother's furniture. It doesn't quite belong here. But unless you are OCD like me it is not noticable. The tiny leather grab handle is utterly useless and looks like it will rip off at any moment. However, because the main cloth strap is so great you will never notice or use the little frail thing. The bottom section should have been reinforced with a tougher leather. For some reason the leather seems softer on the bottom panel of this bag than every where else on the bag. If you tend to drop and drag your Risky Business on the NYC Subway floors or in your Classrooms you may want to glance under there to see what I mean. Again I baby my bag when traveling and it is always on my lap or on the seat next to me so I'm exempt from such tragedy.

That's it for the negatives and those were tiny negatives that 99% of casual users will not even notice in the years of owning this wonderful bag.
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on February 11, 2010
I don't know if its a defect but the leather bleeds color into anything lighter than pitch black. pants that are not black will end up with unsightly black ink marks after a days wear. I am very disappointed in the product considering its suggested retail value.
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on January 11, 2013
I have never written a review for Amazon before, but the issues I have had with this product have led me to do so. Please do not let the high ratings for this bag fool you - the leather bleeds, and will stain your clothes permanently. I have owned this bag (the brown version) for a week and a half, and on 2 light pairs of khaki pants that I must have worn with the bag on over the right pocket for 20 minutes for each pair total, I noticed an unsightly, diffuse brown stain. The leather bleeds, and it bleeds badly. I took it to the cleaners, who tried everything they could, and they told me they couldn't do anything to get the entire stain out. I was shocked, as I have had stains of all sorts before, and this is the first time a stain could not be removed. The cleaners told me that despite what people say, leather should NOT bleed, and even if sometimes it does, who cares if it is going to ruin your clothing after one time use?

I will be returning this bag to Amazon and am getting credited for some of the damages done to my brand new pants, but I am angry that they would sell such a defective product, that is essentially unusable. I am shocked at the high ratings, but can only conclude that the people with the high ratings are either not noticing their stains, are in fact getting better products (i.e., I got a lemon, unlikely considering I read just now some one stars about leather bleeding), or they are only using it with dark pants. I have not had a problem with Amazon before, but I am obviously very angry that $150 worth of new pants are essentially garbage.

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on December 22, 2014
Pictures on Amazon looks very pretty, but the bag I received is not like this.This package has a lot of black spots and surface scratches, looks very ugly, can not be used.
I took a few pictures, it seems very obvious. I was very disappointed with this bag.
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on December 14, 2014
This bag would've been perfect, love the genuine leather too bad it came with a scratch in the front that I'm positive wasn't a packaging problem because it came in a big cardboard box. i wish that wasn't there since i paid for a good bag and its too late for me to return it because i need it by christmas.
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on January 4, 2015
This was disappointing. After only three months and not a lot of use, the inside snap-button has come off.
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on August 19, 2008
I love the look of this bag but the leather rubs off onto my pants. I've had the bag for about 4 months and it still continues to bleed. I tried applying a leather protector but this only helped a little.
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on October 27, 2010
I mainly purchased this bag to carry around things other than my computer, a 15" MBP. I was expecting to only carry a paper notebook or 2 with my iPad and Clear Spot. Maybe a few other things like power adapters, headphones, camera, pens/pencils etc...To my surprise, my MBP fits even with the clear Speck snap-on case attached. I don't plan on carrying it around very much but it's nice to know it's up to the task.
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on January 14, 2016
I have had this bag for a few years and I am ready to replace it. The material is nice and it has a good look but there are things about the bag that make it unsuitable for normal use. My main gripe about that bag is that is can not stay closed. It has two tiny magnets that keep it closed for ascetic purposes but once there are items in the bag like a computer or books, it flies open with normal use. This happens constantly in my car when I brake or when it tips over. Items will fly everywhere. If you have a few papers or a notebook that you need to carry, perhaps this will be a fine man-purse for you, but if you need to carry things that you intend to keep and not bounce around your car, find something that closes.
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