Traveling For Work? Messenger Bag
Just keep it simple and understated–no outside pockets and extra buckles. A streamlined look also makes a statement without being too gaudy. I suggest a cognac or brown leather, as it is appropriate for both casual and formal settings. The beauty of leather is that it also ages more gracefully than other materials.
Remember: if you go any smaller, you have a satchel, which not very many people can pull off. Unless you’re Indiana Jones, you should stick to the messenger bag. It’s a perfect combination of utility and class–large enough to carry laptops and documents, yet small enough to not be overbearing.
Traveling For the Weekend? Duffel Bag
Believe it or not, there is such thing as a sophisticated duffel bag. The term “duffel” doesn’t only apply to sports–with the right combination of canvas and leather, you can turn your 3-day excursions into a fashion statement. I would suggest avoiding all-leather, as it is both expensive and less durable than canvas. While there are no compartments in the bag itself, it is very spacious and offers more than enough room. Follow this rule of thumb: if your excursion is less than 5 days, put aside your roll-aways and roll with a duffel bag.