Get a good briefcase and it will be with you for years, growing better with age and gaining a distinguished patina. Like a fine wine, a beautiful woman or a good pair of shoes, a briefcase gets better with time. Because of this, find one that fits your style and your workload and keep it around for the long haul.
Personally, I don't like to carry a lot of files and paperwork on a daily basis, so I prefer a folio style briefcase, day in and day out. A folio like this Jack George Underarm Briefcase works great. Made from beautiful and distinguished crocodile leather, it becomes more than a briefcase it becomes a wardrobe accessory.
The Le Donne leather flap fold briefcase can store a laptop and the files from work. It comes in a chocolate leather with two different carrying devices. It has a shoulder strap for hands free carrying and a hand strap for ease of use. The key is the hand strap is attached to the case itself and not the flap fold, which is important for carrying heavy loads. This briefcase sells for a reasonable $149, but similar models from other companies can sell for more or less depending on the quality of the leather. The best leathers will be hard at first and will soften with time, cheaper leathers will already be soft at purchase or will feel plastic.
The McKlein Briefcase is an attractive and more formal option than the flap fold briefcase. It has a harder, rigid frame with enveloping front pockets. This design looks best with just a hand strap, but a shoulder strap can be added for airports and when hands free travel is needed. Due to the rigid frame, the laptop will be stored safely and conveniently, while the other files and paperwork can fit in their own pockets. The tan color is quite striking making it a statement piece. No need to match shoes or belts to the color of the briefcase, it is a stand alone piece. But it is nice to have a stand alone piece that looks quite attractive.
Carry your files in style with a good leather briefcase.