Are messenger bags cool for guys to wear?

Picture this:

You’re walking down the street in New York or any other big city. Look around at the young professionals, messengers, and other people hurrying here and there. You’ll see messenger bags everywhere.

But are they cool?

A lot of people, understandably, have mixed feelings on messenger bags. What was once the trademark of a hipster guy is slowly becoming more and more popular and trendy.

I’d go so far as to say that they are most definitely cool, and should be an integral piece of everyone’s wardrobe accessories. I’ll explain why, and show you 3 of the cooler messenger bags you can buy right now.

Don’t want to read the whole thing? Check out the Timbuk2 Command Messenger on Amazon for my top pick for cool messenger bags!

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Casual Cool: The Timbuk2 Command Messenger Bag

So here’s the thing:

If you want to keep it cool and casual with a messenger bag, you can’t go wrong with this stylish bag from Timbuk2.

The best part?

For me, it’s that it comes in a number of color combos that will fit right in with your style. However, this bag also has its functionality on point, too.

Check out these features:

  • Go with the crossbody shoulder strap, or remove it for strap free usage
  • Stealth mode – features “integrated bag silencers” to move quietly (one of my old bags had a noise issue, so this is great)
  • Lots of internal pockets for organization
  • External zip pocket for the stuff you need to grab on the go
  • Can fit an iPad/laptop of different sizes, depending on the size bag you get (13″(S), 15″(M), 17″(L))
  • TSA compliance lets you send your laptop through security without removing it!

Overall, this is a perfect bag if you’re using it for school, weekends, or a more casual office setting. Plus, the many different color stylings it comes in allows you to go from more professional/understated to a bit more wild.

Want to buy one for yourself? Check it out on Amazon here.

Urban Style: The Chrome Citizen Messenger Bag

Here’s another super stylish messenger bag you can’t miss.

From Chrome Industries, the Citizen bag comes in a handful of really cool color combinations that really stand out.

Check out these great features:

  • Waterproof liner keeps your stuff dry in the rain
  • Lifetime warranty from Chrome Industries
  • Can hold up to a 17″ laptop
  • EVA padded shoulder strap and cross-chest load stabilizer for a comfortable carry
  • Velcro and straps keep your stuff safe and the bag closed

All in all, the Chrome Citizen is an amazing bag with a unique, “urban cool” style that will turn heads and get all your stuff where it needs to go!

Check out this messenger bag on Amazon by clicking here.

But what if a messenger bag isn’t for you?

So why should you NOT wear a messenger bag?

If you’re one of those healthy people that likes to bike to work, messenger bags can become a hassle.

They sit relatively low on your back and they rest on one side of your body, they can throw off your balance and cause shoulder pain. Wearing a messenger bag can also cause you to sweat a lot on your lower back.

You may be better off finding an alternative if you bike regularly.

That being said, if you’re not looking to carry more than a laptop, a messenger bag shouldn’t be a problem, even on a bike.

Secondly, messenger bags offer much less support than a traditional backpack. The straps will slip off your shoulder more easily than a backpack would, especially if it’s raining. In addition, the more you need to carry, the less convenient a messenger bag becomes because all the weight is put on one shoulder.

A recap of the downsides:

  • Not the best option for bike riding
  • Offer less support if you carry a lot

Don’t worry, though – I’ve got you covered:

Best Biking Bag: The Under Armour Compel Sling Bag

If you’re looking for something that’s good for biking and is a cross between the messenger bag and backpack form factors, a sling backpack like the Compel sling bag from Under Armour is a perfect choice.

It’s the best of both worlds, and avoids the low-slung and stability issues that a traditional messenger bag has while biking.

Check out these great features:

  • soft-lined laptop sleeve fits your laptop (up to 15″)
  • trademarked “Heatgear” padded strap keeps you comfortable during your ride
  • front zip pocket for keeping your essentials accessible while on the bike
  • water repellent exterior stays breathable
  • side pocket to hold your water bottle

If biking is your thing, keep it stylish with this cool sling bag from Under Armour. Check out the excellent user reviews on Amazon for more info, or go here to purchase one for yourself.

Why you want to have a messenger bag in your wardrobe

Messenger bags have some obvious perks:

  • they are functional – they carry all the things that won’t fit in your pockets in an easily-accessible way
  • they come in a variety of sizes and colors, so they can fit in with your individual style choices
  • they’re a fashion statement, if you want them to be (check out my post here for some awesome high-end bags)

But that’s not why you’re reading this article—you’re wondering if messenger bags are a cool thing for guys to wear.

To really answer that question is a bit complicated.

To really decide whether they’re a stylish thing for a guy to wear or not, you need to know where they come from, the pros/cons, and what your options are.

Ready to have your mind blown? Read on.

What IS a messenger bag, really?

Okay, maybe I was overselling it with the “mind blown” part.

But I really feel strongly about the utility and versatility of messenger bags.

Let’s take a look at what they actually are first.

The name is pretty straightforward, surprisingly. The messenger bag was originally designed for men who worked at the post office so they could have easy access to the letters they were carrying. A long strap would go across the body or over the shoulder, so the postman’s hands would be free as he walked.

For a long time, messenger bags were simply work accessories.

Utility workers, postmen, and bike couriers all used them because they made their jobs easier. When they first came out in the 1950s, it was impossible to find them in stores—companies had them specifically made for their employees. However, they became more popular as time went on, and were suddenly in stores across the country.

This bag on the right is a great example of a more “classic” style messenger bag, the Kattee Crazy Horse. I go more in depth with this bag in my post on getting a great bag on any budget.

If you’re specifically looking for a great leather bag, check out my post on how to get the best leather messenger bag and how to take care of it.

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What are the perks of using a messenger bag?

Messenger bags look professional compared to things like backpacks.

Whether you’re carrying books or a laptop, they’re a great way to walk into work and look like you belong there. If you’re in business, arriving at a meeting with a messenger bag presents a very different visual than arriving with a brightly colored (or even neutral colored) backpack.

Secondly, messenger bags are simply convenient.

Backpacks are filled from top to bottom, and often lack any specific organizational structure. And to top it off, you can’t usually access the items in your backpack while you’re wearing it; a simple search for a pen could turn into a fifteen-minute spectacle. However, you can access a messenger bag while it’s still on your shoulder.

Are messenger bags cool? Check out the Chrome Citizen Messenger BagIt’s also full of pockets, and it’s organized horizontally rather than vertically.

See the bag on the left, the Chrome Industries Citizen messenger. It’s made for fitting a ton of stuff in there, but with a more functional form factor than a backpack.

This is huge as a convenience factor.

Lastly, messenger bags sit very close to your body. Whether you’re waiting in line or sitting on the subway, you’re taking up less space than you would with a backpack.

I know from experience how annoying people with backpacks can be on the train – I silently judge them while wearing my messenger bag.

It’s also easier to move the messenger to your lap, and to keep an eye on it in crowded spaces. Even the best cities have pickpockets!

A recap of the benefits:

  • It can stop you from looking like a college student while you’re at work
  • It’s easier to keep track of your things because it’s more organized
  • It sits closer to your body, so it’s easier to go about your day

Is it practical to use a messenger bag?

Yes and no:

The practicality of a messenger bag entirely depends on your needs, and what you’re looking to do with it. Essentially, it comes down to two main things: how much you need to carry and how long you’re carrying it.

If you’re regularly carrying anything more than a laptop or a few books, a messenger bag won’t be your best bet.

The weight isn’t evenly distributed, so it’s probably going to be more trouble than it’s worth. And even if you’re only carrying a laptop, that can still take a toll on your body if you’re walking around for hours at a time. Messenger bags are best for short, easy commutes.

I certainly wouldn’t be going hiking with one. They’re called “messenger bags” for a reason, after all.

Ready to wrap up?

Are messenger bags really cool? I think so.

Final verdict: are messenger bags a cool thing for guys to wear?

Check this out:

Messenger bags are a great choice for guys.

Well, not exclusively for guys (women have great choices for bags), but they’re a definitely an accessory guys should be proud to wear with style.

As you’ve learned, they can be extremely practical. They were also first worn by men, and have been popular among guys for decades.

There’s nothing wrong with choosing the most practical option to get your things from home to work, or vice versa.

Messenger bags make guys look both urban and mature.

Remember that awesome Chrome Citizen bag we looked at above? Or the Timbuk2 Command? Both amazing bags that have a mature, urban cool look.

While a backpack screams high school or college student, a messenger bag screams young professional (or, in my case, middle aged professional). I’ve taken mine all over the world, from a meeting at Starbucks to a meeting at the Supreme People’s Court in Beijing, China.

They also come in a wide variety of shapes, colors, and sizes so you can find one that matches your style (and is as feminine or masculine as you’d like it to be).

At the end of the day, looking good in a messenger bag comes down to how confident a guy is. If you’re happy with your choice and walk around like you’re proud of it, people will agree that it looks great.

When it comes to men’s fashion, confidence is truly key.

Wear it with pride (and style).

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