Kenneth Cole Risky Business Messenger Bag

Best Messenger Bag to Take To Work

Why people love it
  • High-quality materials (and final product)
  • Perfect for everyday use
  • Comfortable to carry

Watch out for the leather on the first few days out with this. The dye may bleed a little (which means you should buff it out before use).


If you’re looking for affordable sophistication, this is the leather messenger bag for men that you want. It’s perfect for taking to the office (though truly, you shouldn’t schlep your laptop back and forth every day – unless it’s how you watch movies in the evening). The strap is long and the carry handle is perfectly positioned. We love the way the leather feels and the amount of stuff you can get into this bag. The price is rather good (considering), but we do wish there was a way to close this fully.

What’s it made of? Ohhh the leather on this bag is just so lovely. We know you’ll want to snuggle with it, but you shouldn’t; at least, not at first. The leather dye can stain a bit until it’s been worn in. And the lining is polyester, in case you were wondering.

Can you close it fully? Not really. Sorry. We would have loved it if you could, but the front flap is the closure and that’s all you get. Of course, you will find an inner zipper pocket to help keep a few of your belongings secure.

What’s the largest laptop or tablet it can hold? The bag is 16” wide and 12” tall, so you can fit a fairly large laptop inside. And there are phone and front gusset pockets to help organize your smaller stuff.

Can you wash it? It’s leather, please be sensible about how you treat it… even if you aren’t paying a fortune for it. Leather cream or wash is the only advisable option.

Will it break the bank? Depending on the color you choose, you’ll pay somewhere between $80 and $120. That’s pretty stellar considering the list price sits at $300. And, let’s face it, the name alone might be worth the amount you pay.

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