While you may not be delivering messages with this bag, it will deliver your laptop, iPad, headphones, and whatever else you need to your office, coffee shop, or airport of choice in style. We like the darker version of this Estate Messenger from Fossil because it has the black and brown blend of colors meaning you can sling it over a blue button-down or a black v-neck and it will match just as well with each. In terms of toting capacity, this bag will fit a 14" laptop, so if you carry the big boys, this isn't for you, but it can fit a laptop, and iPad, 3 pens, a couple of notebooks and a small umbrella. As a side note, this bag comes with a limited warranty good for a year, so feel free to toss it around. Oh and did we mention it's on sale right now?
Available on sale at Fossil.com for $200 ($100 off)
Full Disclaimer: By clicking "Buy" and purchasing an item from this retailer, we here at What is A Gentleman get a commission that helps keep us up and running.