How to Wear Rock a Messenger Bag

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After about the age of 18, I think you’ll agree that guys find themselves facing something of a dilemma when it comes to carrying our stuff:

On the one hand, backpacks are an extremely efficient way to haul stuff around.

But no matter how hard brands try to make them look ruggedly masculine or sophisticatedly refined, it’s impossible to deny that backpacks evoke a more juvenile time in our lives.

How to Wear a Messenger Bag

As a result, they can easily make grown men look like young schoolboys, which is not the look most of us are going for.

Briefcases, on the other hand, are the height of grown-up sophistication.

Unfortunately, carrying them by hand is both inefficient and annoying.

(Plus, they also tend to look a little too stuffy and business-like for the more casual world in which most of us live and work nowadays.)

Enter the Messenger

How to Wear a Messenger Bag

And that’s where the messenger bag comes in.

Bridging the gap between backpack and briefcase, wearing a messenger bag presents men with a perfect in-between option: 

It allows us to carry our stuff over our shoulders (or actually, shoulder, singular), without looking like an accountant from the 1950s.

Carrying a messenger bag can be a great way to split the difference between youthful and mature.

But making messenger bags look sharp isn’t quite as easy as slapping one over your shoulder and heading out the door.

In this post I’ll show you the ins and outs of how to wear a messenger bag with style.

Plus, I’ll also explain how you can make an over-the-shoulder satchel look sharp as hell, and recommend a few places to pick up good-looking bags.

How to Wear a Messenger Bag

How to Wear a Messenger Bag

Your Guide to Making a Satchel Bag Look Sharp and Stand Out

How to Wear a Messenger Bag

The Best Material and Color(s) for Messenger Bags

How to Wear a Messenger Bag
In your quest to make a messenger bag look great, the first thing you want to consider is the material the bag is made out of.

Leather is the most classic choice for men’s accessories like bags, belts and shoes, and for good reason.

Leather is simultaneously rugged and refined, meaning a leather messenger bag looks just as good at a high powered law firm as it does at a high-powered firing range.

(Would you describe firing ranges as “high-powered”? I know literally nothing about guns. Anyway, what I’m trying to say is that leather is bad-ass.)

How to Choose the Best Color for You

How to Wear a Messenger Bag
As go your belt and shoes, so goes your bag

If you opt for a leather messenger bag, the best practice is to keep the color consistent with any other leather accessories you’re wearing at the time.

So if your shoes and belt are both made of brown leather, then your leather messenger bag would ideally be brown as well.

Of course, this can make things a little bit tricky, because most guys only own one messenger bag, but multiple pairs of shoes, in both brown and black variations. (You do own shoes in both colors, right??)

There are basically three options if you find yourself in this position.

Option 1: Commit to One Color

How to Wear a Messenger Bag
The first option is to assess which color you wear most often, and then buy a leather bag that matches that color.

So if you wear black shoes 80% of the time, you can feel pretty safe investing in a good black leather messenger bag, because it’ll look great the majority of the time.

Option 2: Spring for Both Black and Brown

The second option won’t require you to make any style concessions, but does call for a bit more budget: you could buy two versions of the same messenger bag, one in black and one in brown.

How to Wear a Messenger Bag

This will definitely help you ensure that you’ve always got a sharp option to pair with your shoes, but will obviously require you to pay more for the privilege of perennial style.

A Couple Good Leather Options:
Option 3: Go Grey

How to Wear a Messenger Bag
The third option is to buck the black/brown trend altogether and get a bag in a neutral third color, like grey.

It’s rare to find leather accessories in colors other than black or brown, so if you decide to go this route then I recommend opting for a different material altogether, like canvas.

The nice thing about going grey is that a grey bag can be paired with almost any get up, making it the most versatile option.

The downside is that canvas tends to look a little cheaper and less refined than genuine leather, so while you’ll the color is a safe bet, the trade off is that you give up the rugged refinement that you get with leather.

Deciding which option is right for you is really just a matter of personal preference, how you think the bag will work with the rest of your wardrobe, and of course, budgetary concerns.

Two Good Options in Grey:

How Long is Yours?

(Relax! I meant the length of your bag strap…)
How to Wear a Messenger Bag
As a rule of thumb, the middle of your bag should be in line with your belt

Once you’ve nailed the color, the other big factor in making a messenger bag look good is wearing it at the appropriate length.

The rule of thumb here is for your belt line to hit the middle of the bag when you’ve got it over your shoulder.

If you decide to wear the bag across your torso (more on when – and when not – to do so below), then you’ll probably want to shorten the strap a bit in order to accommodate this.

But if you let the bag just hang off your shoulder against your side, you’ll probably want to keep the strap a little longer. Otherwise your bag will hit somewhere around your ribs rather than at your waist, and look a lot more like a purse than a man bag.

The main thing to remember is that your messenger bag isn’t a backpack, so if you wear it across your back it shouldn’t sit any higher than your lower back.

Of course, you also don’t want it to get in the way of walking or affect your stride in anyway, which is why wearing it right around hip level is usually perfect.

How to Wear a Messenger Bag with a Suit

How to Wear a Messenger Bag

Another nuance worth calling out in detail is the art of pairing a messenger bag with a full suit.

As mentioned, a messenger bag splits the difference between a backpack and a briefcase, and while a messenger can definitely be formal enough to be paired with a suit, there are a few additional details to attend to if you want to make the look work.

With Suits, Your Bag Has to Pair Perfectly

How to Wear a Messenger Bag
We already covered the first consideration at length, which is the color of the bag, and how it relates to the rest of your get up.

But when it comes to suits, nailing the color combo is really non-negotiable.

In my (admittedly absurdly long) post about how to wear a suit, I went on at length about the importance of making sure your all your leather accessories are in the same family.

That absolutely includes your messenger bag, because if you’re going to pair a messenger with a suit, I highly, highly recommend going for a leather bag rather than canvas or another material.

Messenger bags are already a little less formal than briefcases, which would traditionally be paired with suits.

So the best way to make the look work is by opting for a bag that’s on the more refined end of the messenger spectrum, which will look more in line with the sophistication of the suit.

To Cross, or Not to Cross?

The other big consideration when trying to make a messenger look good with a suit is the question of how to wear it:

Do you sling it over your near shoulder and let it hang beside your body, or sling it across the opposite shoulder and wear the strap across your chest?

As a default answer, wearing the bag over your near shoulder and letting it hang at your side should be your first instinct.

How to Wear a Messenger Bag

Why? Because making a suit look great means nailing a lot of details, including everything from the way your tie falls to how much pocket square pops out of your breast pocket.

Slinging a bag across your chest can disrupt that, and make your otherwise precisely styled suit look unkempt and disheveled.

Of course, weight is also a consideration here.

If you find that your bag is so heavy that one shoulder can barely support it, then slinging it across your chest and letting your core bear some of that weight is probably going to be a better idea than letting your bag drag your posture down.

How to Wear a Chrome Messenger Bag

How to Wear a Messenger Bag

Within the wider world of messenger bags, there’s one sub-category of bags that stands out enough to warrant its own set of how-to-wear-it instructions: bags made by Chrome Industries.

While the majority of the tips and recommendations in this post have focused more on bags that put equal emphasis on fashion and function, Chrome bags famously favor the latter.

Play Your Chrome Close to Your Chest Back

How to Wear a Messenger Bag
Because they were designed specifically for cyclists, Chrome bags are worn with much shorter straps than the rest of the messenger bags featured and discussed in this post.

And they incorporate seat belt buckles that give the bag a cool – if decidedly operational – look and feel.

For all intents and purposes, it’s probably helpful to think of a Chrome bag as more of a one-shoulder backpack than what we now think of as a traditional messenger bag.

(Which is ironic, because if you actually work as a bike messenger, the Chrome bag is probably a much better option!)

They’re designed to be worn snugly against your back and hold your torso tightly, so that they don’t jostle around too much as you pedal your way through rush hour traffic.

Rebellious Vibe, Practical Result

As mentioned, Chrome bags were created for bike messengers, who continue to favor them today.

As a result, wearing a Chrome gives off a cool, rebellious vibe that evokes the devil-may-care attitude of urban bike messengers.

Rather than leather, Chrome bags are made from industrial-grade nylon and military-grade truck tarpaulin, and come in multiple color options.

With Chromes you don’t have to worry so much about matching them to the rest of your outfit; in fact, they’re specifically designed to be eye-catching and stand out.

A Couple Chrome Options:
More Options on Amazon

You Know How to Wear a Messenger Bag 

Now Find Out How to Put Your Best Face Forward

How to Wear a Messenger Bag
For reasons that continue to confound me, a lot of guys tend to ignore their accessories.

Which is a shame, because they often make otherwise stylish get ups look a lot less coordinated and polished in the process.

But now that you know how to choose the right messenger bag for your look – and how to wear it the right way! – you can use your bag to elevate your overall appearance.

Of course, accessories are really only one piece of the menswear puzzle.

If you really want to look sharp and stand out, you’ve got to know how to nail the details—all the details.

Enter your email address below and I’ll send you a checklist that will help you do just that, outlining the Nine Details You Need to Nail to step up your style and put your best face forward.

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More Resources ↓
More Advice on Men’s Accessories from Irreverent Gent:
More Advice on Messenger Bags From Around the Web:

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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