I purchased a Michael Kors bag a few months ago. It's fashionable and big enough to hold my laptop (which is essential) but after a few days with it, I realized it's lacking pockets and the shoulder straps aren't wide enough to fit over my shoulder while wearing a jacket. So, in the end, while it's fashionable, it's not comfortable.
Today, I hit the Cole Haan outlet and found a great bag to use for upcoming travel. Tons of pockets - enough spots for a passport, cell phone, camera, chargers, sunglasses, etc. The bag itself can hold a laptop, books, notebooks, water bottle and makeup bag. Even better, the rolled shoulder straps are comfortable on your shoulder and offer enough room to open the bag at a moment's notice to grab what you need.
Some would say an expensive bag is a waste of money -- it's going to scratched in coach, spilled on and stepped on. While that's entirely possible, a real leather bag is thick and the leather lasts, which means you don't have to worry about your belongings ripping through the bottom of the bag while you run through airports to catch your connecting flights.
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