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on December 29, 2013
I was very happy with my purchase, the luggage is stylish and functional. 4 weeks later and carrying only my 15' MacBook Pro as I was walking the strap snapped out of its place making my computer fall to the floor. Huge dent on my computer unibody, I'm surprised the screen is not broken.

I've analyzed the mechanisms of the strap and is visible defective allowing these type of accident to happen.

Will definitely return this unit and need to research what type of help I can get from Kenneth Cole fixing my computer... I know good luck with that!
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on July 10, 2013
I own the Kenneth Cole Risky Business bag Kenneth Cole Risky Business Messenger Bag in brown as well and had that for a good while before switching to this bag. I also own a Kenneth Cole Rest My Case bag Kenneth Cole Reaction Luggage I Rest My Case in black that I was using for work. This bag has replaced both as my go to bag. There are a few reasons for that, which I will go into. I'm not going to go too in depth about the features of the bag, since plenty of other reviews have done that, but want to focus on comparing these three for someone who is considering the other bags.

The Risky Business bag is a really clean looking bag, but has no support in the interior. That meant most of the items inside moved around a lot and it wasn't a very good laptop bag due to the lack of padding on the inside. The structure of the bag was fairly flimsy, so the file folders I used for work got bent up sometimes. The handle on top of that bag wasn't especially usable since there was no structural support for that bag, so grabbing the handle on the run with a full bag sometimes meant things spilling all over the place. The Show Business bag solves the issues of that bag, although looks a little less casual. There are big padded and gusseted compartments on the inside that protect your laptop and papers much better than the Risky Business bag. The clips on the straps also keep the flap secure, which is something the magnets on the Risky Business bag didn't do well. This bag is bigger though, but I think the size increase isn't too big of a jump.

The Rest My Case bag was very professional looking, but I preferred the flap messenger style. The interior of this bag is laid out very similarly, but the flap is nice to have in order to quickly store items without messing with a zipper. There is also a velcro patch that secures the open pocket in the rear, which is nice. Although it would seem like having zippered compartments would be more secure compared to the Show Business bag, I haven't had anything fall out. The flap is also nice for when I don't want to zip close the pockets but still want some type of protection from rain. I will admit that the Rest My Case bag looked more like a laptop bag and much more formal, especially in black, but the Show Business bag bridges the gap between the casual of the Risky Business bag while adding all the strengths of the Rest My Case bag. It looks casual enough in brown leather that I can bring it to the office, but not to the point where it looks like it is just for work, like the Rest My Case bag.

For those considering one of the other bags I mentioned, give this bag some consideration before making your purchase. This bag is more versatile than the other two and combines the best features of both. If I only had to buy one, I would have bought this bag first. Granted, I'm a guy who loves having different accessories (men in a professional environment can only get away with different briefcases/bags, watches, and colored ties to show our individuality most of the time) so I sometimes break out the other two, but if you want a bag that can go from the office to the coffee shop to your weekend out of town without looking out of place in any environment, this is the one.
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on April 16, 2014
It would have costed $50 to replace or fix the strap at a shoe cobbler after the strap broke about 2 months of occasional use as a church bag so I went back to using my old scruffy bag. What a shame.
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on February 21, 2013
The overall feel of the bag is pretty good. The leather seems fairly durable , though I wonder at it's long term lasting capability beyond a few years. I haven't had experience with cow hide before. My cons would be that it could use one or two more pen holds; the design of the buckles has good potential though they feel somewhat flimsy; the leather shoulder pad is stiff and doesn't fit too well over the shoulder, but then I'm skinnier so my case could differ from most.
The bag is a good size, even for me, and I'm more slender than most, weighing about 115 lbs at 5'6". I wear it at a slant on my back which works well; not too big or bulky. I like it's variety of pockets. The main pocket is well padded and could hold a laptop and a few things similar to a small external hard drive in the three separate pockets, as well as at least a couple notebooks before bulkiness started to take place. The rear pockets; one, maybe two notebook's worth of filling each. If you were to keep a USB wall adapter in it, thinner types might be better rather than a block type. The front compartment doesn't give too much space for small bulky items besides what's designed for the small features inside it, as well as a small notebook like a Moleskine. I like the pull-through handle feature, which feels pretty strong, held with both rivets and stitching. The lining of the bag feels like it could wear over time, similar to luggage lining.
Overall I like the bag. Good weight but not too heavy. Being the picky type, I've looked around quite a bit for a good messenger bag, and this is the first I've owned. It has a classy look, modern clothes or business. I'm satisfied with it and interested to see how well it will turn out after a while of use.
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on April 19, 2014
I used this bag for two days and on both occasions after just a few minutes of walking my nice dress slacks were significantly stained black due to the dye bleeding off onto my pants. The first day this happened it was raining, so I gave the bad the benefit of the doubt and tried again. The next day was dry and the same thing happened. This is a messenger bag designed to be worn at someone side! How on earth did this get past quality control if it ruins pants if ones legs rub up against the side while walking. This is even more inexcusable when one considers this is a business bag. Luckily I was not wearing one of my suites....

In addition when the bag is filled up the top opening that hold pens and business cards ect is extremely hard to get into. The sides do not expand at all. This pocket becomes all but useless once I have my lap top and pad-folio in the bag along with a few other small electronics such as my kindle and GPS.

Finally, the two locks for the buckled lengths on the bag up front are extremely difficult to unlock. I wrestled with these for too long and finally opted to just leave these unlocked and just fold the flap over. This was not the end of the world as the two main compartments are zipped.

At the end of the day I do not think anyone at Kenneth Cole actually used a prototype for a day before mass producing these. If your a college student wearing jean and sweats every day and you do not plan on filling this up all the way or making use of the top pouch you may be happy with this bag. If you are a business professional like myself, I recommend you look elsewhere. For now I and going back to commuting with my backpack despite its lack of a professional appearance.
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on October 8, 2012
I rarely buy anything without performing some sort of extensive research on the product. When I decided to upgrade my backpack, I decided to start looking at messenger bags. My goal was to find something that would be professional enough to bring to work, while also being flexible enough to wear in casual settings. I searched on bags from J. Crew, Cole Haan, Kenneth Cole, Coach, Eddie Bauer, and loads of other brands. My ideal bag was leather, buckle straps in the front which locked (instead of actual buckles), large enough to fit a 13"-15" laptop, and reasonably priced. In the end, I almost pounced on the Cole Haan Heritage bag in the Woodbury color, but the price and buckles kept steering me away. Finally, I decided to pull the trigger on this bag based on the price and look of the bag.

This bag did not disappoint.

Liked About the Bag:
- Leather is of good quality
- The bag itself feels very "solid"
- Bag contains a variety of compartments
- One interior compartment is exactly the right size to house my Kindle Paperwhite in its leather case
- Buckles and clasps feel sturdy, give a satisfying click when locked
- Shoulder strap is thick, feels comfortable
- Laptop compartment is well-padded
- Fits underneath the seat on airlines
- Reasonably priced (at the time, $122 for the brown version)

Minor Annoyances Regarding the Bag:
- Getting into the bag, when all the clasps and zippers are in place, can take a while (a bag with magnetic clasps and the main compartment was not zippered would take considerably less time to get into). The pictures may not illustrate it, but there are two zippered compartments (one main, one aux.) which are covered by the leather flap. The zippers run all the way down the side, but you only need to unzip the top of the bag in order to access the contents. So if the bag is closed up all the way, you will need to unbuckle the two clasps in front, lift up the flap, and then unzip the main compartment in order to access (for your laptop, etc). However, there is a front flap compartment (for quick access items such as pens, an ID badge, etc) which immediately accessable once the flap is lifted.
- Bag is slightly larger than expected, but this may end up being a good thing

Strongly Disliked About the Bag:
- Nothing
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on February 25, 2015
Purchased this bag for graduate studies. Perfect fit for iPad, cellphone, battery charger, eye glasses container, external plug & play hard drive, pens, small three ring binder, and notebook. I've loaded this bag to the rim with research articles, text books, technology, and it's done well... until today. The strap finally gave way. Otherwise, for a daily work bag with little weight, it would be perfect. All in all, it was worth the money (lasted into its sixth semester of PhD).
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on August 18, 2013
I read a couple of the negative reviews of this bag and I have no idea what they are talking about. The bag is amazing. It is well laid out and designed very logically. There is just the perfect amount of space for everything without it being too large. I've had this bag for a couple of months now, and the leather appears to be wearing very nicely. The latches took me a couple of days to figure out, but now they are extremely fast and I think it is a very clever and convenient design. I also like the fact that the handle and strap are attached to the body of the bag (not the flap), so if you forget to latch the flap, it's not big deal (it still carries just fine). This bag allows me to be stylish when going to work. It's cool enough to fit my appearance when I'm dressed down in jeans, but nice enough to look good if I need to dress up. It also looks masculine, which is important.
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on May 30, 2013
I read a number of reviews before I bought this laptop bag, and I love it. Some comments on the various reviews.
1. The size as stated on the website is wrong. Two people have pointed it out. The actual size is about 16 x 12 x 4.5 inches instead of 13 x 9 x 4 inches. But that larger size was what I was looking for so I am happy, but Amazon or the manufacturer should change it on the website.
2. The product is advertised as having a “distressed appearance”. Despite this, some reviewers have pointed out that their bags had poorer quality leather. I agree with both parties. The distressed look is real and adds to the appearance. I also had a small “nick/gouge” on the inside surface of bag that probably indicates a poorer quality of the leather. This does not detract from the looks and function of the bag.
3. This is a much softer leather I am used to for laptop bags. It needs a lot more care.
4. There were some issues with clasps being stiff. Mine were perfect, slid in and out the way they should.

The bag was on sale. For this price, this is great value! The shipping box was perfect and opened up nicely to a bag that I was looking for. I use it every day and have made one international trip with it already. Holing up just fine. I would highly recommend this bag.
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on May 25, 2014
I bought this for my work use, replacing a backpack style carrier. The leather and styling is nice. I like the storage and overall look. However some of the support stitching has pulled and some of the leather has torn just after a month or so. It's still holding up at this point but I was disappointed that it showed signs of stress/wear so early. I'd be careful if you are the kind of person that overfills your business carrier, as this may not last as long as desired for that purpose.
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