The Best Leather Messenger Bag [Buyer’s Guide]

The Best Leather Messenger Bag [Buyer’s Guide]

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It doesn’t matter whether you’re interviewing for your first job after college, making your way across campus, or looking to improve your daily appearance—a simple, leather messenger bag is a great way to stand out among the crowd.

They’re professional enough to work in any business setting, but also fashionable enough to have while you’re traveling, in school, or out on the town.

You deserve to look sharp:

Because of this, I’ve tracked down some of the best leather messenger bags and reviewed them here for you.

Don’t want to read the whole post? Check out my top pick, the Fossil Men’s Buckner Workbag, on Amazon.

What's the best leather messenger bag?

Choosing a great leather messenger bag

So you want to buy a new bag?

Messenger bags are one of the most versatile bag options, and a great fit for any man who’s sick of shoving everything in his pockets (or asking someone with a purse to carry it).

Thanks to the variety of shapes, sizes, and colors leather messenger bags come in, you’re sure to find one that meets your needs.

That can also make choosing one very difficult!

The major benefit of using a leather messenger bag is the opportunity to better organize your things (using all those interior and exterior pockets). You can access them more easily than you can with a backpack.

This is because you can swing the bag around easily and dive in. With a backpack, you need to take it off before you go rummaging through it.

Before you buy a bag, it’s important to evaluate any prospective purchase with three metrics:

  1. Fit
  2. Function
  3. and Style/Looks

Let’s break down each one, and then we’ll get to my top bag choices:

Choosing the best leather messenger bag

Choose your fit wisely

It can be hard to find one that’s a messenger bag that’s a perfect fit (but it will happen eventually).

For starters, you need to choose one that’s got an adjustable strap. Without that, you can potentially run into a bunch of problems, like back issues and balance issues when moving around. The bag itself should be around hip-height.

Just pick a strap length that’s comfortable for you.

If your bag is too heavy and it’s giving you problems, either lighten the load (only carry your essentials), carry it by the handle (many leather bags have one), or go with a stylish backpack instead.

Make sure it functions for your needs

Yes, you read that right.

When choosing any accessory, I’d rank functionality above looks any day.

If not for functionality, what the hell are you carrying a messenger bag for? Might as well leave it at home and save yourself the trouble (and money).

What kind of function you’re looking for depends on how you plan to use it:

  • Need a bag that can double as a briefcase for court or business meetings?
  • Want something durable that you can take traveling?
  • Just want a nice looking bag that you can use for your laptop and accessories to lug to the coffee shop for some work?

That function, then, will dictate the looks of the bag.

That’s because leather bags come in a variety of styles, from casual to professional. We’ll go over some right here in this post.

Sizing things up:

The next thing you want to consider when figuring out if a bag fits your needs is size.

The only way you are going to know what size you need is to figure out exactly what you’ll be carrying on an average day.

We recommend that you set aside everything you will be using to put in a bag. This is going to help you judge the size of the bag you need.

On top of that, if you have too much stuff, maybe you should look into an alternative backpack to get. Messenger bags are known to not hold as many items as backpacks, and this is why you need to know the amount of space you will be using.

In fact, if you’re holding too much stuff, you may be heading toward some shoulder and neck injuries.

Not cool! (get a backpack)

With that out of the way, here are my picks for the best leather messenger bags:

My Top Pick: The Fossil Men’s Buckner Workbag

Let me set the scene:

You’ve just started a new job in a more professional environment – could be an office, a law firm, or even a creative studio.

It’s time to ditch the backpack you’ve been using throughout school or on the weekends. You need to step up your style game and look like you deserve the money they’re paying you (and more).

Enter the Fossil Men’s Buckner workbag, a top-quality leather messenger bag that will serve you well throughout your career.

Who’s it for?

Pretty much anyone who’s looking to have a slick, professional leather bag to carry their stuff in. Whether you’re still a college student or you’ve got an office job, you’ll fit right in with this great bag.

Why it’s great

Fossil is known for their watches, but they also craft some great-looking bags.

This one is proof.

The cognac color is a nice deep brown, making the high-quality leather stand out. It also comes in a darker brown color. It also features some beautiful estate brass hardware that will turn heads.

It also comes with a 1-year warranty, in case there are any issues.

Fit and Function

The Buckner bag has a briefcase silhouette with a top handle, making it appropriate for work in an office or other professional environment. However, it’s still got a shoulder strap that will allow you to carry it like a messenger bag.

One potential drawback is that the strap isn’t padded, though users report that the strap itself is soft enough to be comfortable.

The bag’s laptop pocket will hold a laptop up to 16 inches – big enough for most MacBooks and definitely most tablets.

Need storage and organization? The Buckner’s got you covered.

It’s got 2 media pockets for your phones and other devices, 1 main zippered pocket, a key ring, and 4 elastic loops to keep your pens and other small objects organized.

Perfect for taking to your everyday work stuff to the office or to an important meeting.

You can read the excellent reviews for this bag on Amazon, or click here to check the best price.

Looking for a smaller satchel bag to match? Check out the Buckner City Bag as well.

Best bag for Professionals: Saddleback Leather Classic Briefcase

This one is a legend.

Saddleback Leather has been making some of the highest quality leather bags since 2008. They pride themselves on crafting the best products and instilling their values into their business through philanthropic efforts.

Even better, they back up their bag with a 100-year warranty.

That being said…

These bags aren’t cheap. But this is the kind of thing that you get if you’re in a need for a professional briefcase that will turn heads and last forever.

Who’s it for?

This bag from Saddleback Leather is a great choice for someone who really needs to show that they’re serious about business and isn’t afraid to invest in a quality accessory that will get better with age. Lawyers, executives, doctors, entrepreneurs, etc.

Let it not be in doubt:

This is a hard core bag for a professional.

Why it’s great

Probably easier to ask why it isn’t great. But here’s the details:

Saddleback has super high quality control on their products. They use artisan tanneries located in Mexico, which produce leather that they claim will soften and get better with age. Saddleback also prides themselves on the quality of their hardware and even the thread that they use.

Once you see one of these bags, it’s hard not to agree.

They come in two different sizes, as well as a handful of colors to suit your preferences.

The big negative, as I said before, is the cost. But you get what you pay for with leather bags. You’ll see below, when I discuss the different types of leather, that this is made out of the best kind of leather you can buy (full grain).

That ain’t cheap. But it’s so worth it (that new leather smell, for instance)!

Fit and Function

As I said, you can get this briefcase in two different sizes, medium and large. Lots of pockets means great organization and storage: 4 interior pockets and 2 exterior, along with a key strap inside to keep you organized!

As for function, you can carry this bag 3 ways:

  1. as a briefcase, by its top handle
  2. as a messenger bag/satchel, by its strap
  3. as a backpack, by looping the strap through the ring on the center of the bag.

The bag itself has tons of functionality due to its many straps, pockets, and flaps. For instance:

  • You can create a false bottom using one of the flaps to hide your important stuff
  • You can use the side straps for different things, including a tourniquet (great for EDC usage!)
  • The rings on the bag can be used to tie things down, like tripods and camping gear

Not convinced?

Read the user reviews on Amazon here, or click here to check out the latest prices.

Want some more info on how Saddleback creates their products? Check out this tongue-in-cheek video from them on YouTube, “How to Knock Off a Saddleback Briefcase”:

If the cost is still a bit too much for you, even with this high quality – check out this low-cost alternative from DHK.

Budget Professional Style: Kenneth Cole “Come Bag Soon” Leather Messenger

Looking for a stylish leather bag on a sub-$100 budget?

Kenneth Cole’s got a great one for you in their pun-ishly named “Come Bag Soon.”

It’s one of my favorite, not just for its great price, but also because it looks professional without looking too “busy.” It’s also made of gorgeous full grain Colombian leather that will turn heads.

Who’s it for?

A young professional just getting their start, or a student with an office internship who wants “dress to impress.”

Why it’s great

As I said, I’m a big fan of the looks of this bag. It’s just so…clean.

Often, leather bags (even the best ones) tend to over do it with the detailing. I think the Come Bag Soon hits the perfect balance.

You can’t go wrong with any of the 3 stylish colors it comes in, though I’m a fan of the rush cognac color that will help you stand out from the crowd a bit.

Fit and Function

Inside, it’s super functional:

  • Padded laptop pocket for up to a 15.6” screen laptop
  • Additional tablet pocket for your iPad
  • 2 open top inferior pockets with phone and pen holders
  • Rear pocket for easy access on the go
  • Additional zipper pocket inside

It also features an adjustable shoulder strap that’s padded for comfortable carrying.

Final thoughts

Overall, a great leather bag for those on a budget. Kenneth Cole makes great products, and this is no exception. The multiple interior pockets (particularly the dual laptop and tablet spaces) make it functional enough to be your virtual office on the go!

You can check out the available styles and prices on Amazon here.

Budget Manliness: Kattee “Crazy Horse” Briefcase

If you love the look of the Saddleback I reviewed above, but you’re not quite in that price range yet, you’ve got to check out this briefcase/messenger bag.

The “Crazy Horse” from Kattee has that old school masculine style of the more expensive Saddleback, but at a sub-$100 price point.

Who’s it For?

You’ve got a traditional professional job that requires a classic bag style, or want to exude a more masculine vibe through your accessories (rather than minimalist).

Why it’s great

Besides the awesome price point, this bag from Kattee is one of my picks for a few main reasons:

  • A classic look – the stitching and buckles have a rugged, masculine appearance
  • Front buckles are adjustable, so you can potentially increase the interior space
  • It’s built to be sturdy and long-lasting, with high-quality adjustable braided leather strap with a shoulder pad

Fit and Function

Speaking of space, it’s got plenty of interior pockets to keep your stuff organized, including interior zipper and open pockets for things like your phone and other electronics.

It’s also got a rear zipper pocket that’s easily accessible.

My only caveat would be about laptop size – it only holds laptops or tablets up to 14”, so be sure that yours will fit before buying.

Final Thoughts

Overall, this is a great option if you’re looking for a classic look for an accessible price. Once you’ve smelled that new leather smell, you’ll know you made the right choice.

Pick one up on Amazon here.

Top Vintage-Style Bag: Leabags Oxford Leather Messenger

If you’re looking for something with a more vintage style, but still keeping the leather material, Leabags has you covered with their Oxford messenger.

Who’s it for

This is a great option for a man looking to make a bit of a fashion statement. It comes in several unique colors, and has an extremely chic and crisp design. This bag is a particularly good option for men in a professional setting, as its design is both simple and business-minded.

Why it’s great

This is a sturdy bag designed to carry larger loads, and won’t easily show wear and tear. The materials are thick, and it has multiple compartments (which are relatively deep) to stay organized.

Fit and Function

This bag has multiple interior and exterior pockets that seal with Velcro, as well as zippered compartments. These pockets and compartments vary in size, and can carry things ranging from a laptop and textbooks to a water bottle and sneakers. There is a padded laptop sleeve.

For added security, there are internal zippered pockets that are great for wallets, IDs, etc.

Final thoughts

This is a large bag, which is perfect if you have a lot to carry, but can be a bit bulky if you’re not regularly lugging around multiple textbooks. If you’re only carrying a laptop and a few other things, you’re better off going with a smaller option.

However, if you’re a neat freak, this is one of the most organized messenger bags out there.

Check out the best price on Amazon here.

Honorable mentions:

Rustic Town Leather Messenger Bag

Who’s it for

This messenger back is great for the everyday student who is looking for a casual option to carry a laptop and a few books. Whether you’re going to the coffee shop, class, work, or the library, this style of bag fits right in. It’s compact, organized, and attractive.

Why it’s great

This is a good day-to-day bag to carry the essentials. It’s made of canvas, so it can go through quite a lot without showing wear and tear. It also has two exterior pockets, as well as an interior padded laptop sleeve and zippered compartments. The use of both latches and zippers offers added security.

It comes in a variety of colors and sizes, so you can choose one that best fits your needs.

Fit and Function

This messenger bag consists of one main compartment, in addition to small exterior and interior pouches. The main compartment is ideal of carrying books, laptops, and other bulky items, while the smaller pouches are ideal for wallets, keys, pens, and pencils.

Final thoughts

This is a good bag for a college student who is looking to just make it to class and back. It isn’t the best in a professional setting, and won’t fare well in wet weather.

However, it offers just enough organizational options and sturdiness to get the job done.

Click here to check it out on Amazon.

Samsonite Colombian Leather Messenger Bag

Who’s it for

Leather messenger bags are the perfect fit for men who are looking for a professional bag option. This is a versatile design, and is perfect in both formal business settings and the classroom. It’s an especially great fit if you value form over function.

Why it’s great

This messenger bag has a sleek, brown leather finish that looks professional, but not over the top. The addition of a diagonal zipper and a front pocket give it dimension for an added bit of style. The bag sits on your waist and the shoulder strap is thick leather with a supporting pad, making it easy to carry throughout the day.

It is on the smaller side, but that is somewhat typical of leather bags.

Fit and Function

This leather messenger consists of a single main compartment, as well as a padded laptop sleeve. It’s large enough to carry a laptop, as well as books and chargers at the same time. The exterior pocket is perfect for holding wallets, phones, or loose change. There is also an interior and exterior zippered compartment.

Check it out on Amazon to see more info.

Buyer’s Guide for Leather Messenger Bags

Everyone needs to own a great bag.

This is nothing new:

When we first started school we had a backpack. Backpacks with cartoons and logos evolved into more minimal or stylish ones.

But as we grow up and start working for a living, we also need a quality and functional bag to help us carry the things we need.

It is common knowledge that backpacks just aren’t appropriate for a man who is out of college and in the working world. Heck, even a college student can benefit from choosing a messenger bag form factor over a backpack.

To me, it simply looks more professional and stylish. I haven’t seen a backpack yet that looks as good as a nice messenger bag or satchel.

Don’t get me started on those guys who wear a backpack with a suit…

This is why it is important to take some time to find a bag that is going to work the best for you.

Buyer's Guide - the best leather messenger work bags

Why buy a messenger bag?

It’s pretty simple.

They allow you to comfortably carry things on the go. In particular, they are fantastic for on a bike, and they take up less space on the subway or train. They are really useful if you commute to and from work.

Heck, I work from home and still use my messenger bag quite often. Mostly when I pop out to work at a cafe for a change of scenery.

The major benefit of using a leather messenger bag is the opportunity to better organize your things (using all those interior and exterior pockets). You can access them more easily than you can with a backpack.

This is because you can swing the bag around easily and dive in. With a backpack, you need to take it off before you go rummaging through it.

However, there are many brands and styles of messenger bags. It can be quite a hard task to find one that is going to work the best for you

This is why it is so important to take the time to find one that is the best, and really learn how to take care of it.

Best leather bags for work - buyer's guide

Why get a leather bag?

Think long term.

I believe that the best type of messenger bag is one made of a high-quality leather.

The main reason is because you need a bag that is durable and that is going to last a long time. This is crucial, especially when purchasing a high-end bag – you want to get your money’s worth.

Leather is also the most “professional” looking material you can get a bag in. While nylon and canvas have their advantages (water resistance, for starters), a leather bag is on another level of professionalism.

Arguments could be made for non-leather, minimalist or modern bag styles also fitting into a professional environment. However, you came to this page to talk leather, so that’s what we’re going to do!

Once you’ve read through this Buyer’s Guide, you’ll know exactly what to go for and what brands to stay away from.

So, what is it?

Good question!

“Leather” refers to any tanned animal skin, but usually cattle. You can also have kangaroo leather, fish skin leather, and other animal skins. In this post, though, we’ll stick with cows.

Different types of leather

Don’t get fooled:

Just because something is made of leather (or claimed to be), doesn’t make it worth the money. The word “leather” by itself doesn’t really speak to quality.

To know what you’re getting, you need to know the difference between the different types of leather and which to choose.

The main types of leather are:

  1. Full grain
  2. Top grain
  3. Corrected grain
  4. Split leather

Without going too in-depth, just know that the types are differentiated by how much of the original skin and grain are left.

Full grain is the real deal – it’s all there and it’s the best you can get. The best part about full grain is that it develops a beautiful surface patina over its life. It’s breathable and durable, meaning it will perform well and last a long time.

You’re generally going to find this kind of leather used in heavy duty things like shoes and sofas.

The Saddleback Leather bag I reviewed earlier in this post is made of full grain, and it shows (in its beauty, as well as its quality and price).

Top grain is still pretty good, but it has two meaningful differences.

First, it has had one of its layers taken off (the “split” layer, which we’ll talk about in a bit). This makes it a bit thinner, but also helps it to be more pliable and workable. This is one reason why it’s the most common type of leather used in different leather goods.

Second, it has had its top layer sanded and often coated with another material. This helps it be more resistant to stains, but removes that patina that develops over time with the Full Grain.

Corrected Grain leather is a lower quality base layer, with an artificial grain added to it. The manufacturer sands off the natural grain before adding the fake one.

Not optimal, and I wouldn’t want a messenger bag made from this.

Last is something called Split.

This is one of multiple layers of the original leather that has been stripped off. An artificial grain is then added.

This kind of leather is what usually becomes suede. You probably won’t encounter it when looking for a leather messenger bag (hopefully).

Some of the top leather messenger bags out there

Size – How big is your bag?

Now that you’re educated on types, let’s talk size.

You want to consider size carefully when purchasing any kind of bag. For a bag you want to have around for a long time (like a good leather one), you should have a good idea of what size you need before buying!

The only way you are going to know what size you need is to figure out what the purpose of the bag is.

I highly recommend that you lay out everything you will be using to put in a bag. This is going to help you judge the size of the bag you need.

Pro tip: if you have too much stuff to carry, which wouldn’t fit in any normal messenger bag, maybe you should look into an alternative backpack to get.

Messenger bags are known to not hold as many items backpacks, and this is why you need to know the amount of space you will be using.

Some questions to ask:

  • What size laptop do you carry, if any? Tablet? Both?
  • What other bigger items need to fit? Papers and folders? A portable hard drive?
  • When, when, and why will you be carrying it?
  • Will you have time to change out the contents during the day (for example, switching out books in your car or locker at school), or do you need everything with you all day?

Depending on your answers, you could require a bigger bag.

Leather messenger bags for professionals

Durability – Can your bag take some punishment?

Thinking long-term again:

Durability is probably the most important aspect of buying a high-quality leather messenger bag.

You need one that is authentic and made out of high quality material (check the leather types section above).

The main reason for this is, as I mentioned before, you are going to paying a larger price tag on a leather bag than a normal messenger bag made out of canvas or nylon.

However, if you buy one that is durably made out of real and high-quality leather (with perfect stitching), it is actually going to save you money in the long run.

Why is that?

The reason is that any knock-off fake or low-quality leather bag is going to break down on you easily and quickly, you will also have to replace it right away, which will cost you additional money. If you find a bag that is durable, it is going to last you a long time.

Does it have a warranty?

With any high-quality leather messenger bag, you need to find one with a fantastic warranty or guarantee.

This is crucial whenever making a substantial purchase because you need to know that there is a way to get your money back if any of them go defective. Every company can make mistakes, and the best ones (of the biggest brands) will own up to those mistakes if anything goes wrong and it is there fault through the development process.

Please check this out before making a purchase!

Weather Permitting

Don’t buy that bag yet!

You are going to be using this bag in a variety of settings and, as far as I know, you can’t control the weather!

You want to ensure that you bag is at least water resistant, in case you get caught in the rain. Most people carry their laptops and other electronics in a bag, and you want to ensure that your bag is going to protect them.

Some of the lower-end leather messenger bags are also known to bleed if they are not made out of the higher quality leather types. Make sure you read the reviews and product info to know that it can be used in various weather conditions.

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