Best Leather Messenger Bag (2020) Reviews: The Ultimate Buyer’s Guide

Best Leather Messenger Bag

Our Top Pick
Kenneth Cole Reaction
Best Budget Option
DHK Vintage Leather Messenger Bag
Best Luxury Option
FRYE Men’s Logan Messenger Bag
Kenneth Cole Reaction Show Full-Grain Colombian Leather Dual Compartment Flapover 15.6-inch Laptop Business Portfolio, Dark Brown, One Size
DHK 18 Inch Vintage Handmade Leather Messenger Bag Laptop Briefcase Computer Satchel bag For Men (DARK BROWN)
FRYE Men's Logan Messenger Bag
Our Top Pick
Kenneth Cole Reaction
Kenneth Cole Reaction Show Full-Grain Colombian Leather Dual Compartment Flapover 15.6-inch Laptop Business Portfolio, Dark Brown, One Size
Best Budget Option
DHK Vintage Leather Messenger Bag
DHK 18 Inch Vintage Handmade Leather Messenger Bag Laptop Briefcase Computer Satchel bag For Men (DARK BROWN)
Best Luxury Option
FRYE Men’s Logan Messenger Bag
FRYE Men's Logan Messenger Bag

The messenger bag is rapidly becoming an essential accessory for the modern man.

To set yourself out from the crowd and make a fashion statement, one made from leather is an excellent choice.

Fit for almost any occasion, the leather messenger bag will soon become something you’ll never want to leave your side.

Let’s dive into our top messenger bag picks! Here they are…

👑 Our Pick for Best Overall

Sale
Kenneth Cole Reaction
835 Reviews
Kenneth Cole Reaction
The Kenneth Cole Reaction is an excellent leather messenger bag that doesn’t compromise on style or substance. Available at a reasonable price and in several different colours, this should be a strong contender in your search for a messenger bag.

Our Other Top Leather Messenger Bag Picks for Men

  • Our Top Pick: Kenneth Cole Reaction
  • Best Budget Option: DHK Vintage Leather Messenger Bag 
  • Best Luxury Option: FRYE Men’s Logan Messenger Bag

Best Leather Messenger Bag for Men Reviews

Kenneth Cole Reaction (👑 Top Pick)

The best leather messenger bag in our view is the Kenneth Cole Reaction.

The first thing you’ll notice as you look at these bags is how sleek it looks. With a satisfyingly minimalist design this leather bag will compliment just about any outfit, from a casual to a professional context. It’s also available in three striking colours: black, cognac, and dark brown. This means you can pick the model which best fits your wardrobe to elevate your overall style.

What gives this messenger bag it’s pristine aesthetic is the type of leather used. No expense was spared in the making of this bag as it is composed of full-grain Colombian leather. This puts it a level above many other leather messenger bags, and lets people know that you’re serious about your style. Nothing but the best will do.

As a result of the full-grain composition, this bag is highly durable, and should last you a very long time. Even if you get caught in the rain or take a tumble or two while wearing it you shouldn’t notice any wear or tear. That makes it a formidable bag, and one which offers excellent value for the very reasonable asking price.

The straps on the bag offer plenty of flexibility too in terms of the functionality. The shoulder strap ticks the three main boxes of being adjustable, removable, and padded, and the handle on top gives you another way to carry it when it gets too heavy.

It doesn’t end there though, the interior of the bag shines almost as much as the outer shell. Inside the Kenneth Cole Reaction you’ll find several compartments, each serving a different purpose. There’s everything from an accessory pocket, to a padded laptop sleeve, and an important document/mobile phone compartment at the back of the bag.

Features:

  • Available in 3 colours
  • Made from full-grain Colombian leather
  • Holds laptops up to 15.6 inches 
  • Extra compartments
  • Removable, adjustable, and padded strap
    WHY WE CHOSE IT AS OUR TOP PICK:

    Ultimately we chose the Kenneth Cole Reaction bag as the best leather messenger bag for the following reasons:

    1. The Kenneth Cole Reaction has it all. This premium full-grain leather messenger bag is as beautiful on the outside as it is functional on the inside.
    2. All 3 colours are stylish and should fit well with most outfits.
    3. The quality material ensures durability and resistance to general wear and tear.
    4. Many compartments inside the bag make for easy storage of everything from important documents to technology.
    5. The strap has everything you should be looking for – it’s padded, adjustable, and detachable.

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DHK Vintage Leather Messenger Bag (💸 Best on a Budget)

The DHK vintage leather messenger bag is a sturdy option that looks the part while boasting a budget-friendly price tag.

This messenger bag is available in both a 16 and 18 inch size, which means that you can get one whatever size laptop you have. 

The most striking part of this messenger bag is how robust it seems. While many bags have a minimalist aesthetic which makes them seem slightly fragile, this one looks like it’s built to last and withstand some serious punishment. That makes it a fantastic choice for the clumsy and accident-prone, but also anyone looking for the best protection for their goods.

You’ll also notice that there are a couple of pockets on the exterior of the bag. While this may compromise the streamline design that many bags of the same style feature, it adds some useful functionality. The pockets are the perfect sizes for small gadgets like mobile phones, or important documents you may need for travelling. You won’t even need to unfasten the main buckle of the bag to get to them either.

The shoulder strap is a little on the light side, which means you shouldn’t have any problems with a lighter load. Though if you want to carry lots of heavy gear around, the lack of serious padding may be something that you want to think about. Apart from this there’s the briefcase-style handle on top which is always handy.

As for the interior, there are three compartments. The biggest one is in the middle, and is the perfect size for everything from laptops to documents. The other two are smaller, and can be great for laptop accessories like headphones or a charger.

Features:

  • Available in 16 inch and 18 inch sizes
  • Made from genuine leather
  • 3 compartments inside
  • 2 pockets outside
  • Adjustable strap with shoulder pad
Sale
DHK Vintage Leather Messenger Bag
4,063 Reviews
DHK Vintage Leather Messenger Bag
The DHK genuine leather messenger bag is a great budget option which should give you years of use.

FRYE Men’s Logan Messenger Bag (💎 Best Luxury)

The best luxury leather messenger bag we found is the FRYE Logan.

This bag is both effortlessly stylish and pleasingly minimalist. It doesn’t look like much at first glance, but the quality of the material (luxe Italian leather) really shines through on closer inspection. It’s one of those messenger bags that will elevate your style and seamlessly blend in with a variety of outfits. Though it’s possibly best suited to more formal settings due to the classy colours and sleek design.

If you have a reputation to uphold as a man who prides himself on looking the part whatever he’s doing, then you’ll want a leather messenger bag just like this one. It’s a fairly significant investment to justify, but you’ll reap the rewards as you rep this bag for many years to come.

The magnetic flap makes accessing the contents of the bag a breeze, so if you’re always on the move you won’t get frustrated trying to prize open your bag to get your passport or other important documents. There’s also a convenient adjustable shoulder strap that will fit to your body, regardless of height.

On the inside of the bag there are several zip pockets, with more than enough storage space to keep all of your belongings by your side.

Features:

  • Available in 4 colours
  • Adjustable strap
  • Made from luxe Italian leather
FRYE Men’s Logan Messenger Bag
41 Reviews
FRYE Men’s Logan Messenger Bag
If you’re looking for a stylish Italian leather messenger bag that oozes elegance, then you’d struggle to find a better option than this one.

Samsonite Colombian Leather Messenger Bag

Known for its high quality luggage and portable storage, Samsonite is a reliable brand to look to for a leather messenger bag.

This messenger bag is made from Colombian leather so you know it’s the real deal. The leather is complemented well by antique brass hardware that gives the bag a sophisticated look.

As you might already know though, Samsonite’s bags are designed first and foremost for functionality and durability. That means what you can expect with this messenger bag is one which is ideal for travel, and for holding all of your valuables securely. What makes it suitable for travel is the briefcase-style design along with the removable shoulder strap, making it easy to go through airport security when you need to.

Also on the subject of functionality, the interior of this messenger bag is perfect for carrying everything from documents to gadgets. For a start there’s the organise under the front flap which has several zip pockets and small compartments for business cards, passports, and other small bits. Then there’s the three interior pockets which include a padded laptop sleeve, and finally the rear compartment which is for any paperwork you may need to bring with you on business trips.

Features:

  • Available in 2 colours
  • Made from Colombian leather
  • Removable, adjustable, padded shoulder strap
  • Fits laptops up to 15.6 inches

Summary

The Samsonite leather messenger bag is a fantastic choice for the frequent flyer due to the ample storage space and durable leather design.

Ultimate Buyer’s Guide

You typically have to invest a substantial amount of money to get a top quality leather messenger bag, so it pays to make the right choice first time.

Even if you’re not planning on breaking the bank to get your bag, you’ll want to go through a mental checklist to get the best one for your needs.

The main criteria that should come to mind when considering a leather messenger bag are the quality of leather, the storage options, and the craftsmanship.

What follows is an extensive list of the key factors that should be taken into account in order to make an informed decision.

Leather Quality

As with pretty much any leather fashion accessory, you’ll want to aim for the highest quality grain available in your price range.

The quality of leather is determined by the grain, which we’ll get into briefly.

However it’s also entirely possible that you aren’t too concerned with the actual quality of the material, but rather, how it looks.

In which case you can largely disregard this information, and instead opt for the bag which has the aesthetic you’re looking for.

Although different grains of leather do have varying levels of durability and weather-resistance, so that’s something worth paying attention to.

Full Grain 

Full grain, or top grain leather as it’s otherwise known, is the highest quality grain.

Taken from the top part of the animal hide, this type of leather is thick, sturdy, and will look every bit as rugged and authentic as leather gets.

This leather is taken from cowhide and showcases all the richness and luxury of the material at its best, as any imperfections are ironed out.

A full grain leather messenger bag will last you anywhere up to a lifetime, so it’s a very safe investment.

Full grain leather is also a very water-resistant, stain-proof material so you don’t have to worry about wear and tear quite so much.

As you might imagine, securing this type of leather bag will set you back a decent sum, so make sure it fits your needs perfectly before pulling the trigger.

Genuine 

While you know you’re getting a real leather product when you see the word genuine, it doesn’t necessarily suggest anything about the quality of the material.

Interestingly, since it’s easy to think that genuine implies quality, a lot of people believe this is as good as it gets.

Unfortunately, the opposite is closer to the truth.

Genuine leather is material that passes as leather, so in some cases it’s a marketing trick to convince you of quality that may not be there.

That’s not to say that a messenger bag made from genuine leather won’t look good or stand up to wear and tear, but it does tend to suggest a lower level of quality.

This type of leather is best for the casual use messenger bag or for the budget investment.

Suede

Suede leather is one of the least expensive types, and much like genuine leather, it doesn’t scream quality.

Taken from the bottom part of the animal hide, suede is a good option for the budget messenger bag.

Faux

Faux leather is a whole different matter.

The first thing to recognise is that it isn’t considered real leather, as it uses alternatives to animal hides.

The use of synthetic materials has several implications for the end product.

For a start, the quality will be noticeably lower than with real leather. That’s unavoidable.

But, there are a variety of reasons why an investment in a faux leather bag can be a good decision.

Since faux leather is constructed from various synthetic materials, it can adopt different qualities.

One of the more common types used for messenger bags is polyurethane leather.

This faux leather, often referred to as PU leather, is soft to the touch and highly resistant to scratching, abrasion, and peeling.

It’s also a very environmentally-conscious material which is an extra bonus. 

Storage Space

With regards to storage space, there are a couple of things to look out for.

Of course the first thing you should consider is the size of your laptop and whether or not it will fit, and then there’s any additional compartments you might need.

The primary function of a messenger bag is holding your laptop as you move around, so making sure that your device fits is crucial.

Laptop Size

The messenger bag will typically accommodate laptops in the range of 11″-17″. This allows plenty of room for anything as small as a notebook, but also leaves open the possibility to carry around a larger unit.

Selecting a bag that fits the measurements of your laptop should be easy, but there’s one other factor you should keep in mind.

If you have a small laptop now, but at some point in the future you could see yourself investing in a larger one, then maybe you want your bag to be a bit larger than your current machine.

This may seem insignificant, but if you’re looking to splash out on an expensive designer leather bag, and it is rendered useless in a few years when you buy a new laptop then you’ll be left needing a new one.

Extra Compartments

In terms of the other compartments and storage space of your dream messenger bag, you need to factor in everything that you might want to have access to when you’re out and about.

If you need your laptop for work, then what accessories are imperative to bring along? 

Chargers can take up a lot of space, as can over the ear headphones and other peripherals you may use with your laptop.

It can be a good idea to lay out your laptop and everything you use with it on a flat surface, and then you’ll have a clear idea of the storage space you’ll need.

Aside from electronics, are you going to need an extra compartment for important work documents or personal items?

If so, do you need them to be a certain size and/or depth?

Again either mentally or physically lay out everything you’ll want to take in your messenger bag, and then choose accordingly.

The last thing you want is to buy a brand new leather messenger bag, only to realise after a day or two that it lacks the storage space you need.

Craftsmanship 

Just as the interior of any messenger bag is important, so is the exterior.

The craftsmanship of a leather bag could play a big role in your decision-making process, since it will determine how practical and comfortable it is to use on a regular basis.

There are a few different exterior elements of any messenger bag that we’re going to take a look at now.

The Buckle

First up is one of the least glamorous elements of a messenger bag: the buckle.

While it may not be the first thing that springs to mind as you’re looking for your perfect leather messenger bag, the buckle can be very important.

Its primary role of course is to make the bag as easy to close as possible, and convenient to do with one hand.

This heightens the portability of the bag, and lets you do things like reach in and grab important documents should you need them while travelling.

The buckle also plays a large role in the overall style of the bag, and could make the difference between a good bag and a great one.

The method of fastening is the main way in which they differ, so let’s take a look at the most common types of buckle you’ll find.

  •  Traditional. The traditional buckle isn’t the most easily fastened, but it does boast a classic style that is appealing to many. It’s also one of the most secure buckles once closed, so you can rest assured that any important electronics or documents inside are safely hidden and difficult to get to.
  •  Single Clasp. The single clasp buckle will open with a simple press of a button, giving you easy access to your goods. Unfortunately, that also makes it one of the least secure options, since it doesn’t present much of a challenge to open. However, the best part of this single clasp design is that you can open it with one hand, so if you’re always on the go or on the phone then this could be just what you need in a messenger bag.
  •  Magnetic. The magnetic style buckle is similar to the single clasp in that it is easily opened, and fastened. A snap of the buckle is all it takes to access whatever’s inside your messenger bag and it’s a pleasing action. Again, caution when using this style buckle in a crowded urban environment, since it can be just as easy for someone else to get into it.

The Strap

The strap of a messenger bag is what makes it such an essential purchase for the modern man who’s always on the go.

A shoulder strap is designed for superior convenience and comfort, and unlike a backpack, will only go over one of your shoulders.

This usually makes the messenger bag much lighter than a backpack, and more suited to travel.

But this isn’t the only strap you’ll find on a lot of messenger bags.

There’s also typically a shorter handle-like strap on the top of the bag, like the one you see on briefcases, but slightly more comfortable and flexible in nature.

As for what you should look out for in a strap, it should fulfil the following three criteria:

  • 1) Adjustability

Adjustability is something you probably shouldn’t negotiate on. If your shoulder strap isn’t adjustable, then you won’t be able to find the perfect fit as you walk around.

Even if the strap seems to be ideal for your needs, you never know when you might need to loosen it to lighten the burden or make it tighter to keep your valuables closer to you.

2) Height

Then there’s the other key factor: height.

If you’re tall, you’re going to need a very different length for a shoulder strap than someone who is of average height. Likewise, when you plan on wearing the bag can have a big impact on the length of strap you need. Walking requires a different fit than cycling or travelling by scooter for example

  • 3) Detachability 

While this is one factor that isn’t 100% necessary in a leather messenger bag, it can be a huge benefit.

The idea behind a detachable strap is that you can easily reduce it to a briefcase-style size if you have to go through airport security or attend a business meeting.

Another situation in which it comes in handy is if you ever have a lot of heavy goods in the bag.In this case, you’ll most likely want to carry it by the handle, and as such, you probably won’t want a long shoulder strap dangling close to the floor.

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Comfort

Another non-negotiable factor in the craftsmanship of the bag you choose should be comfort.

If you’ve carried a messenger bag around for an extended period of time before, you’ll know that it can get uncomfortable before long.

That’s why it’s essential that you find one with padded shoulder straps, so it doesn’t feel like the strap is digging into your shoulders and neck so much.

If you have to move around a lot with your belongings, then you want to know that you have a comfortable way of doing so.

After all, the messenger bag is meant to be a practical accessory you wear often, not one you use once every blue moon.

Colour

The colour of your leather messenger bag may not seem like the most important factor at first, but if you are fashion-conscious at all then it’s worth taking into account.

As with any men’s fashion accessory, there are some loose rules and guidelines to follow to pull off a stylish look.

One such unwritten rule is the idea that there should be some element of coherence in your outfit.

For example, your belt and shoes should typically be a similar colour. You wouldn’t necessarily wear a black belt with yellow shoes, unless you were looking to make a bold statement.

As such, your leather messenger bag should fall in line with the colours you tend to wear on a regular basis.

If you have a lot of blacks and browns in your wardrobe, then you’re in luck.

The most classic styles of leather messenger bags often come in these two colours, since it’s hard to go wrong with either.

The colour you go for should not only go with what’s in your current wardrobe, but also coincide with the context you plan on wearing it in.

For example, black is one of the best colours for a formal business setting, whereas variations of brown can work well with casual wear.

Extra Features

Not all messenger bags are created equal, while the mention of one might bring to mind thoughts of a rectangular bag with two compartments and a shoulder strap, there are several worthwhile features to look out for.

  •  RFID-Blocking Technology

RFID (Radio-frequency identification) is a form of technology which is integrated in passports and credit cards. It’s also a means through which data from your gadgets can be retrieved or stolen digitally via the process of skimming.

Some messenger bags can largely omit the risk of being a victim of this type of identity theft through RFID-blocking technology. 

They do this through the pockets you’d use to store your electronics. The logo on the pocket tells you that your gadgets and personal information will be safe from digital theft as you’re out and about. 

This is especially useful if you have to travel a lot for work and have your credit cards and laptop with you.

While some people claim that the risk of being on the receiving end of RFID skimming is rare, it’s best to be sure when it comes to something so important.

  •  Phone Pouch

Some messenger bags will have a special pocket which is designed to carry important possessions like your mobile phone, passport, or other small documents.

This is useful if you prefer not to have the bulge of your mobile phone protrude from your pant pockets, and also if you want to spend some time without access to social media.

It can also be a great place to store important documents like a passport and others that you need to be able to access quickly while travelling.

  •  Padded Laptop Compartment

This is a big one if you carry your laptop around with you a lot.

To ensure the best protection for your electronics, it’s useful to find a messenger bag with a padded sleeve or compartment.

This will come in handy if you ever drop your bag or fall over while in a hurry – it happens to the best of us!

Price

The price you pay for a leather messenger bag will depend largely on one factor: the quality of the leather.

As we looked at earlier, leather comes in various grains, each with its own characteristics and level of quality.

The more complete the grain, the higher the quality. At the top end, you have what’s known as top or full grain leather. This is what you should look for if you want the most premium quality.

At the lower (and cheaper) end of the spectrum you have genuine leather, and faux leather.

To figure out how much you should put down on a leather messenger bag, it’s worth asking yourself a few questions:

  1. Do you care about having the best quality? If so, then your only real option is to splash out on a full/top grain leather bag. One excellent option we’d recommend is the FRYE Logan bag, which is made from 100% full grain leather.
  2. Do you want a messenger bag that will last longer than a few years? If this is the case, then you’re going to want to find one that’s highly durable. The most durable type of leather is full grain, but you can also find some great faux leather bags that are designed to last a long time.
  3. For this purpose we’d recommend a sturdy built one like the DHK messenger bag.
  4. Are you looking for a bag that’s resistant to rain and/or wear and tear? Water-resistance along with abrasion and scratch-resistance can be hugely important features to look for in a messenger bag. A bag with these features will extend the lifespan of the bag, and preserve its original aesthetic. For this purpose we’d highly recommend our top pick the Kenneth Cole Reaction which is designed to withstand a lot of punishment.

Frequently Asked Questions About Leather Messenger Bags 

Do messenger bags look good on guys?

Originally a style of bag worn only by those delivering goods, the messenger bag has soared in popularity in recent years as a men’s fashion accessory.

The modern man has to go about his business without compromising a keen sense of style. As a result, accessories like the messenger bag come in handy as they are one of the best ways to carry a laptop around for work.

Since it has become so ubiquitous amongst men, it only makes sense that brands focus on creating bespoke options that compliment all kinds of styles.

There are few better accompaniments these days than a high quality leather messenger bag slung over one’s shoulder. The messenger bag is rapidly becoming the new briefcase, and in a lot of cases provides a more versatile and more stylish form of mobile storage.

Are messenger bags out of style?

No, if anything, messenger bags are more in style in 2020 than ever before!

The reason why messenger bags have stuck around for so long as a staple in most men’s looks, is because of its great utility and ability to elevate a style.

Now more than ever it’s common to travel for work or move from one spot to another in search of WiFi in the case of working remotely.

With this being the case, it’s important that you have something that you can easily pack your laptop and other important equipment in at a moment’s notice.

Alternatives like the backpack can still be a popular choice, but the move towards favouring more minimalist options renders them redundant for certain purposes.

Briefcases are still perfectly stylish and functional too, but they lack the same convenience of a messenger bag which can be carried in a variety of ways.

What’s more, the messenger bag is suitable for many different uses. Whether you’re dressed in casual wear or something more formal, you can pull off a well-chosen bag.

Who makes the best leather messenger bags?

The great thing about leather messenger bags is that there is a healthy amount of competition between brands.

That means more choice for you as the consumer, and more affordable pricing for the most part.

Unlike some areas of fashion like shirts or polos, it’s difficult to pinpoint a single brand which makes the best leather messenger bags.

With that in mind, here are some of the top brands known for producing quality leather bags.

  • Kenneth Cole

Kenneth Cole is an American brand focussing on urban gear, offering everything from luxury shoes to designer watches.

What makes it a great choice for the leather messenger bags is their simple yet elegant designs, built for the urban man and his needs.

You shouldn’t expect to find a cheap option with Kenneth Cole, and that’s for good reason. It’s leather bags are designed with top quality faux or real leather which should leave a lasting impression.

An investment in a Kenneth Cole messenger bag should elevate your urban style without taking anything away from a minimalist look.

  • FRYE

FRYE is a US-based leather accessory manufacturer that started out in 1863.

It’s dedicated to providing the best in premium products, boasting gorgeous leather and fine craftsmanship.

FRYE bags are a bold statement, and an excellent way to introduce a touch of class to your outfit, if you have the budget.

  • Samsonite

Perhaps a surprising brand to see as a top leather bag producer, Samsonite offers a great selection of quality messenger bags.

Primarily known for its incredibly durable luggage and bags, you know you can expect a long-lasting investment should you choose to invest in a Samsonite messenger bag.

It’s bags have their own distinct styles, many of them featuring lots of convenient pockets and features, as you’d expect from a brand that specialises in portable storage solutions.

Is it OK for a man to carry a bag?

Absolutely! In fact, we would strongly recommend that you carry a bag.

For a start, a messenger bag is highly practical.

If you’ve ever fancied going to a cafe and bringing your laptop along to do some work or general productivity, then you know the struggle.

Beyond that, this style of bag is very in fashion, and can compliment an outfit well.

Whatever the context, whether you’re wearing a shirt and jeans or a suit, you can find a messenger bag to match.

The messenger bag is becoming as important an accessory to the modern man as the designer watch or stylish belt.

A Final Word on Leather Messenger Bags

Leather messenger bags can do a lot for you in terms of both style and function, so they’re well worth every penny you spend on them.

Find the bag that best matches your most common look, and you’ll have a fashionable accessory you’ll want by your side at all times.

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