Picture the scenario; you’re stood in the store, looking for a messenger bag. The sheer range of choice is overwhelming. There are all sorts of materials, textures, sizes and shapes on offer. How on earth do you whittle down the options to one?

Fear not! Today I’m going to teach you how to pick out your perfect bag. Although I’m using messenger bags in this example, the rules still apply to all other styles including briefcases and sports bags.

Step 1: What do you need?

This is the most vital stage of all! Think carefully about the practicalities and peculiarities you’ll be experiencing with your messenger bag. Do you need plenty of pocket flaps for your phone, PDA and keys or are you going for something more clean-cut? Are you the sort of guy that likes using oversized pads and large files, or are you more into compact notebooks and pocket pens? Are you going to be lugging large quantities of heavy textbooks around campus, or just a thin wad of plain paper? Is your bag going to be exposed to the elements as you catch the train, or is it only going to sit in a warm, dry car all day?

Take a cue from your peers. Examine what they like to use on a day to day basis. You’ll find that certain professions have their own idiosyncrasies for a reason. However, don’t settle for an identical match! Certainly consider structure, size and shape, but be sure to take design in your own personal direction too.

Step 2: What do you want?

Now you’ve decided what you need, consider what you want. Remember, this is an item that may be with you for quite some time, so don’t start impulse buying something you’re not entirely sure about: Take your time! Think about how long it takes you to buy shoes; you find a pair that looks good, you try them on, have a quick stride around the store to make sure they’re comfortable and only then splash the cash – your bag shouldn’t be any different!

Try to wear your typical, everyday clothing whilst testing your choices out. Sure that gingham looks funky with your stonewashed jeans and russet polo neck, but are you going to feel the same way when turning up for an important meeting? I think not… Temper your personal aesthetics against your needs. Remember, needs always come before preferences!

Step 3: The Elimination

So you’re in the store. You now need to eliminate all the choices that don’t match your requirements. Let’s take a look at a few theoretical choices and decide what we like and what we don’t about each one. In this example, I’m going to pretend to be a mid-twenties graduate starting out at a high-brow advertising firm:

Bag #1

canvas messenger bags

The first bag as a series of really nice checks – all the rage nowadays; it’s coated in all the colours I love and it goes beyond the everyday designs you’d see in the street.

However, this response is a perfect example of skipping the most important step; were I a grad-student looking for a school messenger bag, it might be a perfect choice, but I don’t think this is going to send the right message to potential clients, even in a moderate industry like advertising where a messenger bag would be an acceptable choice of entry-level attire. As it stands, this isn’t a very practical choice and my head will have to rule my heart on this occasion; this bag will have to remain on the shelf!

Bag #2

messenger bag

Now this is more like it. It’s solid black leather with a subtle texture and bright buckle clasp. I’d probably fit right in were I to choose this bag. It ticks all the right boxes as far as dimensions go too.

But let’s be honest here – this isn’t really me. It’s too austere and I’d get sick to the back teeth of it before too long. Again, it’s a nice try, but it doesn’t match my personality at all!

Bag #3

the perfect messenger bag

I think we finally have a winner. It’s subtle, simple and professional without looking too generic. It’s not going to look like every other bag in the building, but I won’t look like I’ve stepped straight out of junior high either; it sits in a nice middle ground between the two.

Let’s just take a second or two to take a look at one more bag before buying. I don’t want to simply grab the first one I see; I need some time to reflect and gather a few more options before my purchase.

Bag #4

school messenger bags

Okay, this is completely wrong; I’m beyond all the novelty designs at this point and this only serves to heighten my previous choice as the outright winner. Let’s leave this one alone, grab bag number three and head for the checkout.

About The Author

Johnathan Bell is the founder, owner and main author of Guy Style Guide, a website dedicated to everyday male fashion, style and grooming. The primary mission? To guide clueless men through the tricky mindfield that is the growing world of male couture. Find him on , Twitter and Tumblr.

7 Responses

  1. Blank Label

    i love leather bags! especially brown / tan bags =)
    #3 is an awesome pick. the fabric is pretty sweet. it matches a charcoal suit i have =)

  2. Johnathan

    I rather like them both too, and if I were to choose it’d still probably be number three 🙂

    Thanks for the comment.

  3. Rev

    What stores might you suggest to purchase a messenger bag?

    • Johnathan

      There are plenty of stores around that sell messenger bags – take a look at the ‘Online Stores’ list to your right for a better idea of what’s available. Don’t be afraid to visit local male clothing retailers and taking a look at what they’ve got in store too.

      Thanks for the comment 😉

  4. Michelle

    I love the bag you picked. Where did you purchase it? I can’t find it or a similar one anywhere!

  5. Clay

    Thanks for this article. I have been looking for a messenger bag for a while, and feel like I can choose a bag that actually “works” for me.