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Rolling Laptop Bags: Totally Geeky or Geek Chic?

I'm about to go on a trip soon, so I've been doing a mental checklist of things to pack and trying to do everything to make my trip smooth and easy. This list from Wired is making me want to optimize how efficiently I can get through the airport, so much so that I was reconsidering whether my laptop bag was the best bet, or if I should spring for a wheeled-laptop tote for travel, like this Lodis Audrey bag, or this baby blue wheelie by Willowbrook.
But then I stopped considering it when I thought I might be wheeling my laptop bag. In school, rolling your bag behind you was just something you did not do. Am I old enough or big enough to not care about that stuff anymore and see it as geek chic? I don't know! What do you think?

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