How to Wear a Messenger Bag

A messenger bag is a timeless accessory that goes with multiple styles. We’ve long been advocates for a messenger bag as a stylish men’s accessory - if it’s done right!

Due to their practical size and (usually) understated look, they’ve been a go-to choice for professionals, students, and fashion enthusiasts for decades.

However, finding a bag that perfectly captures your sense of personal style can be challenging. Luckily, messenger bags are easy to style, and there are several ways you can make the most out of your trusty bag.

Choose the Right Bag

OK, let’s start with an obvious statement:

You should pick a messenger bag that aligns with your fashion preferences right from the start.

Think about what message you want to send:

Formal or Casual?

The bag’s most popular designs are the standard casual option and the more polished briefcase-like model.

Both have a striking appearance, but the standard option is more suitable for casual outings when you want to pack a few more items.

More formal models that give off the sleek feel of a briefcase are perfect for business settings where you want a bag that signals professionalism.

Typically, the more external pockets a bag has, the less formal and more tactical it looks.

Consider Leather, Canvas, or Nylon

Most models are made from canvas or leather. Depending on their material, messenger bags complement different aesthetics.

Leather can give a bag a more formal look, but material alone does not determine price or construction quality. Read the leather description alongside the stitching, lining, and hardware.

They’re also more formal and are often seen on young professionals and people committed to growing their business. For a blend of style and formality, faux leather options are available too.

Comfort depends on the strap, empty weight, and what you put inside. A simple faux-leather design can still have the same “I’m someone to take seriously” vibe.

Canvas bags come in plenty of colors and prints, from inexpensive everyday designs to specialist bags. This variety is excellent for choosing a simple and practical bag whose image gives it a dash of individuality.

If you’re on the fence about committing to leather or canvas, consider investing in a nylon bag. Nylon comes in many weights and finishes, and is worth considering if you prefer a less formal look. For a more polished nylon option, take a look at Tumi — if your budget allows it, we’re fans!

OK, so you’ve decided on formality and materials - what’s next?

Neutral or Bold Colors

If you’re the type of person that likes to commit to a single bag, you should probably look at a messenger bag in a classic, neutral color like black, grey, or beige.

Then, even when you switch up your style game, the bag will keep up with you and won’t clash with the rest of your look.

However, a bold-colored bag makes a statement as an accessory. A playful, bright messenger bag can turn a simple monochrome outfit into a real statement.

Our take? As we’ve said - you should think of this as part of your style. So unless you wear the same clothes every day … why wouldn’t you have more than one bag? Perhaps the formal one for the big meetings, and a funkier one for the weekend look.

A stylish leather messenger that works across most of these scenarios:

See on Amazon

OK, we’re ready now, right?

Not quite - there’s one more factor, that’s actually the most important one:

Dress For Your Body Size

This is something we see men getting wrong all the time.

When wearing any bag, just as with clothes, it’s essential that you know which designs show your stature in the best possible light.

Remember - we’re looking at this a style accessory not just a utility.

For Smaller Guys: If you have a smaller body frame, choosing a small-to-medium sized messenger bag will avoid you looking swamped.

Instead of looking too large to carry, an appropriately-sized bag will flatter your stature. Most messenger bags contain several internal compartments, so even a small or medium model is capable of handling a surprising number of items.

Check the bag against your frame while it contains your usual load, rather than judging only an empty product photograph.

For Bigger Guys: The opposite is also true. A larger bag can look more proportionate on a bigger frame, but choose the size that holds your essentials comfortably. Check the strap’s maximum length as well as the bag dimensions.

How To Actually Wear a Messenger Bag

OK, we’ve picked a style that sends the message we want about who we are. We’ve picked the right material, and we’ve picked one that looks right on our frame.

Now, how do you actually wear one?

Wear It Crossbody-Style

This is the really obvious way to wear a messenger bag.

Put the strap on one shoulder and drape the strap across your chest, with the bag sitting on the opposite side of your body.

Start with the bag resting near your hip, then shorten or lengthen the strap until you can walk freely and reach the opening. Avoid a position that bumps your legs or makes you lean to compensate for the load.

Crossbody carry helps keep the bag attached as you move, but it still hangs from one shoulder. Keep the contents light, place the padded section on your shoulder, and change sides when your bag’s strap arrangement allows it.

Swing the bag forward to reach the pockets, or closer to your back while walking. If your bag has a stabilizing strap, use it to limit swinging. Timbuk2’s Classic Messenger instructions show how its adjustable strap, padding, and stabilizer work; follow your own model’s hardware instructions.

Same-Shoulder Carry

You can, of course, sling the bag over the same shoulder the bag is on so it doesn’t go across your body.

We don’t like this option so much, for two reasons:

The weight is all on one side. That may be fine for short bursts, but longer term might hurt your back
If you did pick a particularly small messenger bag, this can give off “it’s a man-purse” vibes

Carry It By Hand

Some models are designed to offer single-hand carrying with handles as well as the strap. This is more of a “satchel” option than a messenger bag, but they still look great, and it’s good to have the option to switch up your look now and then.

When using the handles to carry the bag you should remove the strap, or tuck it inside. This results in clean lines and stops the strap getting dirty by dragging along the ground.