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There are two primary considerations you need to keep in mind when choosing a messenger bag: use and style. The first has to do with how you will be using your new bag (e.g. serious outdoor activities), and the second has to do with what you will be wearing with it on primarily (i.e. tone and taste matching).

First, is the bag going to need to be extremely water-proof (e.g. because you will be biking to work in the rain) or is it more just a fashion choice (e.g. it looks 'cooler' than a backpack)? If you need it to resist rain significantly more, you'll want to look for a bag that has a special water-proof liner that wraps up and around the items inside. Alternatively, some messenger bags have more elaborate systems of fastening the bag exterior that keep rain out, even if it is being driven in horizontally by win. For this kind of bag you will want to go to a store like REI or EMS in your area - somewhere dedicated to outdoor sports and activities.

If your bag is mostly just for show and going to school or work by bus or car, you can go with a more conventional fold-over messenger bag. These come in a great variety of styles, from featuring prominent logos, drawings or other images to simply featuring one to three colors in a straightforward block-stripe pattern. Certainly the former type of bag is more 'expressive' but the latter is more versatile. The basic question in terms of color becomes: what will you be wearing with your bag? If you tend toward earth tones (green, tan, brown, beige, etc...) you will want to find a bag that shares those colors and will compliment your outfit. If you wear mostly greys, blacks or otherwise saturated colors, a bag with a similar tonal palate is more appropriate (burgundy, forest green, dark blue, etc...). When you go shopping take along your favorite or most typical outfit to help you make your selection.

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