The Best Messenger Bags for 2019

Much like a comfortable pair of walking shoes, choosing the right travel bag is so important. Along with being big enough to store all your essentials, the perfect option should be lightweight, comfortable, and free up your hands to do more important stuff like take memorable travel photos — which is why we love messenger bags so much.

These sleek crossbody carryalls will not only keep your belongings safe and organized, but they also offer ample room to store all the items you couldn’t fit inside your suitcase. The best part? These unisex bags are super versatile and look good with just about every outfit imaginable.

Related: 19 Stylish and Sturdy Laptop Bags for Business Travelers

Similar to other travel bags, the number of messenger bags in stores can feel overwhelming. To help you find the best options available, we turned to real reviews from customers to see which ones they love the most.

These best-selling products not only have countless glowing reviews, but they also have thousands of five-star ratings between them. Some of the items on this list feature anti-theft technology, while others boast padded straps for added comfort and a plethora of different compartments and pockets so you’ll never have to waste time searching for stuff.

From sleek leather messenger bags to eco-friendly cotton carryalls, keep reading to see the 13 messenger bags shoppers can’t stop raving about.

These are the best messenger bags to buy:

1. Best Overall: Kenneth Cole Reaction Risky Business Messenger Bag

2. Best Expandable Option: Ytonet Expandable Messenger Laptop Bag

3. Best Leather Option: Frye Logan Messenger Bag

4. Most Comfortable Option: Timbuk2 Classic Messenger Bag

5. Best Eco-Friendly Option: Everest Large Cotton Messenger Bag

6. Most Organized Option: Samsonite Flap Over Messenger Bag

7. Best for Left-Handed Wearers: Chrome Mini Metro Messenger Bag

8. Best for Frequent Flyers: Timbuk2 Command TSA-friendly Messenger Bag

9. Best Anti-Theft Option: LXY Small Messenger Bag

10. Best Canvas Option: Vagabond Traveler Canvas Messenger Bag

11. Best Long Option: Leaper Retro Messenger Bag

12. Best Padded Option: Filson Padded Messenger Bag

13. Best Waterproof Option: Peacechaos Waterproof Messenger Bag

Best Overall: Kenneth Cole Reaction Risky Business Messenger Bag

With over 1,200 reviews, this sleek messenger bag by Kenneth Cole Reaction is one of the most popular options at eBags, and it’s easy to see why. Along with a spacious main compartment, the leather bag boasts an adjustable padded shoulder strap, a cute flap-over closure, and plenty of pockets to keep your belongings organized. It comes in three neutral colors, and 92 percent of shoppers are such big fans of the stylish carryall they said they would recommend it to others.

To buy: ebags.com, $137, (originally $300)

Best Expandable Option: Ytonet Expandable Messenger Laptop Bag

If you ever find yourself needing more space in your bag while you’re out and about, consider this expandable travel briefcase from Ytonet. The work-ready messenger bag comes with a padded laptop sleeve and ten pockets and compartments to hold essentials like your cell phone, pens, tablets, and more. Plus, it can easily expand from seven inches to nine inches wide just by unzipping the expansion zipper. Over 1,100 Amazon customers love the water-resistant bag, with one writing, “I bought this because I travel a lot for work. First, the expandable option is super convenient. As a salesman, I have many catalogs and marketing material and this bag fits everything I need. The quality is top notch as well. You will not be disappointed in buying this.”

To buy: amazon.com, $33

Best Leather Option: Frye Logan Messenger Bag

Frye has been making high-quality leather goods for over 150 years, and this sleek and supple messenger bag is no different. The roomy interior is big enough to fit a laptop, water bottle, notebook, and more, while the magnetic flap closure will keep your belongings safe and secure. Nordstrom customers have given it an impressive 4.5-star rating, praising its timeless design and quality construction. One customer wrote, “This bag has been around the world with me on business for four years. About 45 trips overseas. Perfect carry on for laptop, iPad etc. Goes overhead and doesn't spill. Easy to move thru airport with. Looks great in the boardroom too!”

To buy: nordstrom.com, $498

Most Comfortable Option: Timbuk2 Classic Messenger Bag

Unlike other bags which can hurt your back and shoulders while carrying them, this Timbuk2 messenger bag features an incredibly comfortable airmesh strap pad to keep your shoulder pain-free all day. It also boasts a top handle for easy grabbing, a water bottle pocket, and compression straps for a secure closure. The cute carryall comes in ten different colorways, and over 650 Zappos customers have given it their seal of approval.

To buy: zappos.com, $99

Best Eco-Friendly Option: Everest Large Cotton Messenger Bag

Prefer to use eco-friendly products? Opt for a 100 percent cotton messenger bag like this option by Everest. The roomy accessory can fit everything from binders to laptops to books and more. More than 400 eBags customers have given the beloved travel bag an impressive 4.4-star rating and 90 percent of them say they would recommend it to others. “I was looking for a usable messenger bag with my everyday personal and professional work. This bag is attractive, full of pockets, flaps, and space. I am more than pleased with this item,” said one reviewer.

To buy: ebags.com, $40

Most Organized Option: Samsonite Flap Over Messenger Bag

You’ll never have to endlessly search through your bag to find something again thanks to this hyper-organized messenger bag by Samsonite. The sleek leather accessory boasts a spacious interior, multiple compartments, and an organizer under the front flap that has special pockets for pens, phone, business cards, and more. With details like this, it makes sense that over 1,900 Amazon customers have given it a 4.4-star rating. “The bag is great! It looks extremely professional, and, despite the more than reasonable price, the construction very sturdy. I must give extra kudos for the many compartments that help you stay organized, especially while traveling between business meetings for which you must have multiple things with you,” raved one customer.

To buy: amazon.com, $107 (originally $150)

Best for Left-Handed Wearers: Chrome Mini Metro Messenger Bag

While most messenger bags accommodate right-handed wearers, this cute option from Chrome is designed to be comfortable for both lefties and righties. The roomy bag is big enough to fit a 15-inch laptop along with other daily essentials, and it features a seatbelt release clasp on the shoulder strap that doubles as a bottle opener. “This is a great messenger bag! Besides getting lots of compliments this bag is well constructed and durable. The bag is very comfortable over the shoulder and literally hugs you without feeling bulky,” wrote one reviewer.

To buy: zappos.com, $120

Best for Frequent Flyers: Timbuk2 Command TSA-friendly Messenger Bag

If you fly a lot, you’ll love this messenger bag from Timbuk2. The sleek accessory is TSA-compliant so you won’t have to take your electronics out as you go through security. Along with an interior organizer for smaller items, the bag also boasts a comfortable strap pad and sturdy aluminum hooks that will keep the inside contents secure. It also features a slot on the back of the bag so you can hook the bag around the handle of your rolling luggage. One happy customer wrote, “Very pleased with this bag — it provides protection for my laptop and easy to access storage compartments. Nice looking, comfortable shoulder strap are added features.”

To buy: ebags.com, $75 (originally $150)

Best Anti-Theft Option: LXY Small Messenger Bag

This slim messenger bag from LXY has a hidden zipper to help prevent thefts from occurring, plus six pockets to store and organize your belongings. What’s more, it also boasts an RFID-blocking pocket so you can keep all your personal information safe from digital hackers. The sturdy bag has an impressive 4.6-star rating on Amazon, with one reviewer writing, “This bag is amazing for every type of person. There are great pockets and very lightweight.”

To buy: amazon.com, $23

Best Canvas Option: Vagabond Traveler Canvas Messenger Bag

In the market for a durable canvas messenger bag? Consider this option from Vagabond Traveler. It boasts a spacious main compartment, side pockets, and an adjustable strap. The casual bag’s brass hardware makes it look polished, while the flap-over panel keeps your belongings in place. There are six stylish colors to choose from, and 93 percent of shoppers said they would recommend the carryall to others. “I was looking for a casual messenger bag and this one is great. The fabric and construction are sturdy, it's attractive without looking too busy. My 15-inch laptop is a perfect fit with room to spare for cords and gear. The carry strap is wide enough to be comfortable. Entirely pleased with the purchase, a good value,” said one customer.

To buy: ebags.com, $83 (originally $128)

Best Long Option: Leaper Retro Messenger Bag

Unlike other messenger bags which are horizontally shaped, this vertical option from Leaper Retro will help evenly distribute the bag’s weight across your body. The stylish bag features smooth zippers, magnetic snap closures, a padded strap, and plenty of pockets. More than 1,200 Amazon customers are fans and have given the travel-ready accessory a 4.5-star rating — in fact, it’s the number one best-selling messenger bag on the retailer right now. One customer raved, “This messenger bag is awesome! It fits my 13" MacBook Pro perfectly — like it was made for it. You cannot beat the price for this bag. I’ve had it for a few weeks now and it has held up well and it looks great. I get a lot of compliments on it. I searched hard and long for the perfect size bag and this is it. You will not be disappointed.”

To buy: amazon.com, from $29

Best Padded Option: Filson Padded Messenger Bag

If you are carrying precious cargo like laptops, tablets, and other expensive electronics, opt for a fully padded messenger bag that will keep the contents safe and protected like this Filson option. The high-quality padded twill bag features an adjustable shoulder strap, multiple pockets, and a secure snap and zip closure. One perfect five-star review said, “There is no bag better than this, and it will last a lifetime.”

To buy: nordstrom.com, $425

Best Waterproof Option: Peacechaos Waterproof Messenger Bag

This Peacechaos messenger bag is made from a waxed canvas that is not only super durable but also waterproof. The shoulder strap is fully adjustable, and the carryall can be worn as both a shoulder bag and a crossbody bag. The leather accents give the casual bag a polished feel while the interior pockets help keep everything organized. “I predominantly use the bag while traveling. The waxed canvas is perfect during the rain. Stitches are strong and I throw everything in it, even an extra sweatshirt so I can use it as a pillow while on the plane. It’s just the right size. I have received a number of compliments,” said one customer.

To buy: amazon.com, $41