The cheapest on our list but extremely good looking nonetheless, the Kenneth Cole Reaction Risky Business is one elegant and super comfortable leather messenger bag that can even act as a briefcase when needed.
It’s crafted out of Colombian leather, it has a fully polyester lined interior, contrast stitching, padded adjustable shoulder straps, two front pockets with organizers for cell phones, pens and cards, and dual magnetic closures under the flap.
Risky Business is available in a few different tones of brown and black, looking cool and matching almost any outfit you might have, business or casual. The price of this bag is a decent $79.
9. J. Stark Prospect – $209
Looking more casual than business, J. Stark’s Prospect Briefcase is more of a sturdy carryall option for commuters or day field trips.
Made from waxed cotton with a rugged, good looking finish and bridle leather shoulder straps and handles, the Prospect surely has a lot of appeal for people who want both a very practical, tough and water resistant bag for daily use in the city and outside it as well.
The bag has excellent organizing options, with a main compartment large enough to fit a 15 inch laptop, and smaller interior organizer pockets for various other accessories. The price tag is a good $209.
8. Dr. Martens 15-Inch Satchel – $240
The iconic Dr. Martens comes on the market with an old style and very classic look, the 15-Inch Satchel. The bag comes in black or brown suede leather or tan and wine naturesse, complete with classic shaped brass buckle closures and hardware.
As the name implies, the bag can accommodate a 15 inch laptop and has two main compartments, good for a laptop and a tablet or the device plus all the cords, or papers and documents. The price for this classic beauty is $240.
7. Bed Stu Nigel – $375
The Bed Stu Nigel is a traditional looking briefcase that will take your style to the next level. Made to match even the most demanding business attire, this brief adds that trendy and cool vintage aspect that the modern business man is looking for.
Made from premium leather, with fixed dual handle straps and a removable shoulder strap for the long city walk. It comes with a soft polyester interior lining, a large slip pocket and a few more zip organizer pockets. The price tag for this cool looking briefcase is a good $375.
6. Frye Logan Messenger Bag – $498
For those who’re into sturdy but stylish messenger bags, the Frye Logan Messenger Bag should be their top choice. It has a real classic look and feel to it, but comes with a lot of sophistication nonetheless.
The multiple pouches are perfect for organizing your gear and accessories and the leather build and jacquard lining make for an astonishing look, upgrading your outfit a little more. On the other hand, your wallet will get a downgrade, for the price of the Frye Logan Messenger Bag is a lofty $498.
5. Shinola North/South Leather Messenger Bag – $695
Modern looking but with a classic touch, the Shinola North/South Leather Messenger Bag is a wonderful way to carry your daily accessories from point A to point B and even use it as a carry-on during short flights.
It won’t fit a laptop, but it’s enough for those looking for a minimalist and very stylish way to carry their phone, wallet and the occasional book around with ease. The light brown leather looks amazing and fits both business and casual outfits as well. The price though, is not one to fit all wallets, since it’s soaring to a good $695.
4. Tumi Sawyer – $745
Next on our list is a bag that fits both the formal business man and the digital savvy professional. The Tumi Sawyer is stylish and sturdy at the same time. Made from solid water resistant fabric and leather, plus chrome retractable handles, the bag is built to withstand frequent use.
It comes in black and navy-blue and features a padded compartment for 15 inch laptops, microfiber suede lined tablet pocket, a special pocket shielded against ID theft, magnetic zippers and other pouches for accessory organizing. The price is a special one as well, rising to $745.
3. Mulberry Brynmore Leather Messenger Bag – $1,270
Another carefully designed and stylish brown leather messenger bag for the modern man is the Mulberry Brynmore. It comes in a variety of shades of brown, with sturdy fabric shoulder straps and twist lock fastenings that ensure a bit more security for your belongings.
While it’s not intended for the modern digital nomad, the modern business man will surely find it attractive. Especially since its price will be a sign of pride and wealth for the owner. It’s a whooping $1,270.
2. Smythson Burlington Large Messenger Bag – $1,695
The Smythson Burlington Large Messenger Bag will make any man’s journey as elegant and organized as it can ever be. It’s soft to touch thanks to the deerskin used for fabrication and it’s large enough to carry all your daily essentials both in the city or by air.
Efficient, spacious and extremely elegant, the Smythson Burlington Large Messenger Bag will never disappoint the modern man. It comes with generous interior space for papers or tech, enough pockets for organizing accessories, adjustable shoulder strap and a huge price tag: $1,695.
1. Tom Ford, Briefcase With Horn Closure – $2,420
World renowned Tom Ford comes out on top on our list due to its minimalist design briefcase, crafted with amazing attention to detail and a style that would leave any modern man longing for one.
The briefcase has all the features a true business man would ever need from it. Made from pebbled calf leather, the bag is able to withstand a lot of abuse and still come out stylish for the next business meeting.
It has a lot of room for holding business papers, documents or tech gadgets and comes with a plush leather panel on the interior that splits and better organizes the space. Make no mistake, this Tom Ford briefcase is tough and stylish but also demanding from your wallet. It costs a tremendous $2,420.
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