The 10 Best Cool Bags
Special Honors
Prada Modern Line They’re far from inexpensive, but for those who feel comfortable in this lofty price range, Prada has some seriously stylish offerings. From cross-body bags to backpacks and totes, these luxury models exude sophistication. Many are available in a variety of colors. prada.com
Aer City Sling While its capacity won’t match that of a spacious briefcase or bulky backpack, this slim sling bag is super convenient for bopping around the city. Its webbing strap slides comfortably over your shoulder, positioning it in a way that minimizes any potential irritation. It has a secret wallet pocket, too. aersf.com
Pad & Quill Messenger This one hits the sweet spot — pricier than a basic, no-frills bag, but more affordable than a luxury designer product. In addition to protection, its leather front flap adds a stylish flair, and a quick-access outer pocket is great for reading materials like newspapers or magazines. padandquill.com
Editor's Notes
June 19, 2020:
Removed the Youngerbaby Outdoor and CoolBell Briefcase in favor of better options that are currently available.
We had to modify the listing of the Fjallraven Duffel to indicate that it’s only available in black and red designs, not the wide variety of colors in which it was previously offered. In looking over the KomalC Buffalo Hunter, we noted that users appreciate its ability to stand upright when set on a surface, so we made sure to mention that attribute in the description.
We opted to add a couple messenger style bags to the list. The Timbuk2 Classic offers a traditional style, and we’ve noted that its bike light attachment loop makes it a good choice for those who commute on two wheels. The Egoelife LB is an exceptional value, serving the needs of both young professionals and university students admirably.
When making a choice, one aspect we encourage users to look into: water bottle storage. We often noticed comments and complaints regarding the size and functionality of the various water bottle holding mechanisms associated with these bags, and when you consider that many of us take a container of water with us wherever we go, it’s clearly worth giving some thought to.
October 15, 2018:
Dropped the Birchirly Vintage a bit in the rankings after discovering that the strap’s seams lack reliable strength. Consistent reports of high value, affordability and versatility led me to move the Youngerbaby Outdoor up to a higher slot.
What Makes A Bag Cool?
Others will take big risks with their shape, but come in more traditional materials and dyes.
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.
Choosing Your Cool Bag
When it comes time to choose the cool bag for you, it’s likely that one is simply going to speak to you more than any of the others, that it will connect with that part of you that’s constructed an ego image of yourself that is nearly impossible to shake. You’re likely to disregard the available features that other bags may boast over the one that catches your eye, and you may even be willing to spend more regardless of whether the bag you like is any better or more durable than others.
Also, consider your comfort level when looking at how a given bag is intended to be carried.
So, what can we offer you that’s really going to help? Well, in the event that more than one bag catches your eye, you’re going to need to dive deeply into all those features you were ready to ignore.
Before anything else, you should take stock of what you want to carry. This will tell you how big of a bag you need, and what relative shape it should be. A narrow sling bag, for example, won’t do you very much good if you need it to tote around a 17-inch gaming laptop. It will also tell you what level of water resistance you might want, as well as any padding you’ll need to protect your items.
Also, consider your comfort level when looking at how a given bag is intended to be carried. You’re likely to find duffle bags, messenger bags, backpacks, and sling bags on the market, each of which offers a different carrying experience that could be a hassle in certain situations and an asset in others.
Other Fashion Essentials
Once you’ve picked out your bag, you may find yourself attracted to other cool accessories out there. But which of these is truly essential?
Just make sure you limit clashing styles and colors to fewer, smaller items, and you’ll have a unique look that doesn’t cross into dangerous fashion waters.
Your shoes are one of the most potentially eye-catching aspects of your wardrobe, and they’re likely one that you’re going to use more than one day each week with different outfits. There’s good news here if you want to be a little more expressive with your kicks, as well. Remember how a good timeless look leaned on one or two flashy aspects at most? The same can be said for your overall attire. You can pair a hot, colorful set of kicks with a more conservative suit for a daring ensemble, or dress up a T-shirt and jeans with a monk-strap loafer. Just make sure you limit clashing styles and colors to fewer, smaller items, and you’ll have a unique look that doesn’t cross into dangerous fashion waters.
For most, a quality watch is also a must-have. Luxury watches are out of the price range for many, but they’re a great place to look for inspiration, after which you can find knock-off versions by no-name brands, as well as similar versions by respectable, but not astronomically expensive brands if you want something a little more reliable.