The 10 Best Cool Bags

So, you want to be cool. It’s understandable. There are a lot of cool people out there, and they all seem to be shoving their coolness in your face at regular intervals: gracing the fronts of magazines, playing the best roles in movies and on television, and occupying the most popular places of honor in your school or office.

The thing about being cool is that it relies more on you not trying to be cool than anything else. Trying to be cool only makes you seem desperate, and desperation is generally considered uncool. The more specific aspects of coolness will have a lot to do with your age. Younger people tend to associate coolness with a disregard for things, and showing too much admiration for anything (other than the occasional musician) is often met with suspicion. Showing disdain for pretty much everything? Now, that’s cool. At least until you’re about 27. After that (presumably because you failed to get into the 27 Club), most people begin to express their coolness in a more positive way, and to form strong bonds with people that share their passions.

The irony is that many youngsters are so concerned with looking cool that they fail to cultivate much in the way of actual personality, and many end up resembling one another for little other than their vagueness simply because they’re scared that if they show how much they like anything, they’ll be ridiculed. The internet and its hoards of bullies and trolls have only made this feeling more intense. But you stop caring about that as you get older (remember: less desperate translates to more cool).

Fashion, however, represents a choice at any age. It is an undeniable statement of preference for one item of clothing over all others. So, how do you find an item that can make you look cool no matter your age or generation? The answer lies in a little fashion secret known as timelessness.

You may notice that most of the cool bags on the market have something in common: they limit their flair to two or fewer aspects of their design. Some will have bold colors, but a traditional shape. Others will take big risks with their shape, but come in more traditional materials and dyes. Others, still, will have simple shapes, colors, and materials, but sport a single, bold accent like a colored zipper or a particular logo.

When you strategically limit these defining characteristics, you get a bag that looks like it could have existed 50 years ago as easily at it exists today. It will never look dated the way a neon vinyl backpack from the 1980s with a giant neon pink Nike logo will. Understatement is the essence of timelessness.

That makes these cool bags particularly well-suited for younger demographics that want their secret passions to remain anonymous until they’re safe from scrutiny. But it also provides older fashionistas with a bag that can pull double-duty as a professional carry-all and a personal form of expression. In the latter case, these bags serve as blank canvases on which you can proudly throw that Star Wars patch or paint a portrait of your dog.