Saddleback

Nailing the balance of cool-but-not-girly is a rare and impressive feat for leather messenger bags, so I gathered the best examples for this list. I spent nearly a decade personally wear-testing these bags and visiting multiple bag factories. All of them are durable, suitable for everyday carry, and cool. They're all the "best" leather messenger bag in different ways; consider this a list rather than a ranking: https://youtu.be/YJf1ynl7UYk Our Top Leather Messenger Bag Picks Best Overall: Cravar F.C. 15 ($425) Best Leather: Satchel & Page Mailbag ($545) Best Value: Thursday Boot Co Commuter Bag ($349) Most Sustainable: Bleu de Chauffe Eclair Postman Bag ($445) Most Rugged: Saddleback Leather Flight Bag ($599) Best Overall: Cravar F.C. Leather Messenger Bag I use my Cravar F.C. bag more than my other bags because the F.C. is my coolest leather bag. It's not like it's bristling with tech, but you can feel that it has been designed with extreme thoughtfulness: memorable, not ostentatious, and with a good amount of pockets. What I Like Unique design: casual, functional, thoughtful, and low-key all at once No breakable parts Finished edges (some bound, some waxed) Lining protects contents (a favorite of photographers) Lots of colors and sizes available Made by a small and cool Indonesian brand, which is cool Lifetime warranty A not professional shot from my Instagram stories to show that I really do use it all the time, and it just gets better with age. Downsides But Not Dealbreakers No laptop sleeve (but they'll add one for a surcharge) See the scuff in that picture above? The dye isn't penetrated super deep into the leather The lining is acrylic, some customers prefer natural fabric Note these handy, book-sized pockets that are hidden under the front flap. Features / Specs / Leather Wide range of vegetable tanned leathers Lots of cool, thoughtful non-leather options, like locally sourced, Indonesian denim Good amount of pockets and no breakable parts 15.5" x 12" x 5" (15.2-liter capacity) Padded and articulated shoulder strap was remarkably comfortable, I found https://www.youtube.com/watch?vz1Uw5RKh5aU I made sure to visit the founder when I was traveling through Indonesia – after I'd already spent years using his bags. The straps' load dispersing design keeps the holes in the stud closure system from stretching out. So the bag is surprisingly secure; even though it's easy to open on-the-go, the studs have never, ever come undone. Also, there are three sizes in tons of leathers. It's way, way more range than you ever find with brands like this. There are heaps of different colors and sizes of the F.C.,, from black to green and a few cotton versions too. Price and Value $425 for the larger F.C.s, $385 for the 13-inch ones, $355 for 11 inches Price includes shipping from Indonesia, relax Besides the cool story and unique look, another cool thing about buying Cravar's F.C is supporting a small brand where your dollar is very meaningful. I'd have liked a zippered pocket somewhere and the lack of a laptop sleeve is surprising, but if that's your dealbreaker, they told me they'll add one for you for an extra $20. Or you can peep their R.F. and Rana bags. Their Mailbag in the light, showing more color depth than your average veg tanned leather Best Leather: Satchel & Page Mailbag Satchel & Page’s Mailbag captures the vibe of "high quality but easy to dress down" better than any bag I've seen. It's the perfect choice for guys who want a messenger that's uncomplicated and masculine. What I Like My all time favorite bag leather Tanned the old-fashioned way in Tuscany Secure design while easy to open and close Padded laptop sleeve secured with its own stud closure Available in a smaller size that still looks great Lifetime warranty There aren't a ton of features, but minimalism is just what a lot of guys want in a messenger. Downsides But Not Dealbreakers No zipper closure pockets It's unlined; might feel less "luxury" to you Features / Specs / Leather Vegetable tanned leather will age wonderfully Certified by Tuscany's consortium of vegetable tanners 12" x 16" x 4.5" (14.1-liter capacity) 4 pounds Padded, suede-lined shoulder strap for comfort Listen, I've been to tanneries all over the world and seen almost every leather there is. There are different priorities for boot leather and jacket leather and bag leather. And when it comes to bag leather, the Mailbag's veg tanned leather is simply unmatched. 💡 Tanneries use natural plant extracts to make vegetable-tanned leather, creating a tougher material that develops character but costs more and starts out stiff. Learn more → I would have loved a zippered pocket to stash extra valuables. The simplicity might feel sparse to some, especially with the lack of lining, and minimally finished edges. But you get a padded laptop sleeve with a good amount of pockets and sleeves where I pop my wallet and phone. Instagram stories, I posted the very month that I'm writing this — yup, I use this bag a lot. I could buff those scratches out if I wanted to, but I don't! Value $545 There's a slimmer version for just under $500. Ths a fair price for the lifetime — no, generations of use you'll get from this bag. Listen, here's the thing: in your mind's eye, far in the future, I know you've envisioned a messenger that is old as shit and looks absolutely incredible. This is the leather that will take you to that vision. Further Reading Best Leather Briefcases for Men: High-End, Budget, Vintage, and More We spent over a decade testing leather briefcases before landing on our top ones. Learn more → Best Value: Thursday Boot Co Commuter Bag This next one might be the most versatile in its ability to be used as both a nice briefcase and a casual satchel. Since you can use it in so many situations and it's the least expensive on this list, Thursday's Commuter gives lots and lots of messenger for the money. What I Like Best value and lowest price on this list Huge range of colors and leathers and canvas versions available Super versatile, works as a casual messenger or smart briefcase Many kinds of pockets and options for organizing belongings Level of finishing, like the rolled edges, is uncommon at this pricepoint Chrome tanned leather is softer and feels more "broken in" compared to pricier veg tan leathers Tons of pockets, compartments, and zippers both inside and outside this bag. Downsides But Not Dealbreakers Some prefer stiffer vegetable tanned leather Lined with polyester, some prefer natural fabrics The shoulder pad is a bit slick Carry handles dangle outward when not in use The Commuter also comes in a few canvas colors, which I prefer when I'm wearing a leather jacket and kangaroo leather boots. Features / Specs Two full length exterior pockets Internal laptop compartment and 4 zippered pockets 16.5" x 11.25" x 3.5" (10.6-liter capacity) 6 leathers, 3 canvases available Thursday is really good at versatility. After all, they made their name by combining work boots and dress boots with Thursday's Captain boot. Likewise, the Commuter is a neat balance of smart and casual. It even has leather counters on the edges, like boots do on the heels. Price $349 (less for canvas) The lowest price on this list, yes, but it's not built like most cheap bags. Notice they're using large pieces of leather that span its length, bags at this price point usually save money using lots of smaller pieces. You might prefer veg tan leather or a "we fix it no matter what" kind of warranty, but if what you prioritize is function, versatility, and value, this is what you want. Most Sustainable: Bleu de Chauffe Postman When it comes to longlasting leather bags, a lot of designs lean "rugged American mountain man," but I love the different vibe of Bleu de Chauffe. Their designs are still brings inspired by vintage workwear (in this case, old postman bags), but they're inspired by the rich history of French workwear. The "Eclair" postman bag is the best known of their collection. Also, this bag is a favorite of the photographers I know. What I Like 3 sizes available Veg tan leather in an impressive range of colors Ethically handmade in the French countryside Pretty well priced, given all that Hidden, quick-release closure system Zippered internal pocket; rare in this game Downsides But Not Dealbreakers The (bestselling) Medium doesn't fit my 16-inch laptop No pockets are accessible without opening the bag Edges are raw and unfinished: it works with the design ethos, but you might prefer more refined finishing https://www.youtube.com/watch?v25KqlRLYYEI Features / Specs / Leather 15" x 11" x 4" for the Medium, but there are other sizes External front pocket and internal zippered pocket (none accessible without opening the bag) Felted laptop sleeve (Medium just fits 13-inch models) Popular for carrying cameras Bag opens easily with hidden quick-release snaps Unusually soft vegetable tanned leather available in several colors I like the zippered internal pocket, since many of these brands avoid zippers because they're a breakable part. (It's easier to give a lifetime warranty if there's no zipper.) I'd normally consider the buckle closure a con because it's more clumsy to open and close when you're on the go. But the buckles are basically decorative, concealing a quick-release stud closure system beneath them. I love the bag, but Stridewise contributor Mike takes better pictures of it! Price ~$440 for Medium, ~$515 for Large (depends on the exchange rate) For a vegetable tanned leather bag that's made in a highly developed country, this is really good value. No other brand on this list gets both of those qualities at a lower price. Another cool thing about the way it's made is that instead of an assembly line model, it's one craftsperson making your bag from start to finish — then they sign the inside. Many fans of such handmade products like them because they have a more human touch than mass produced stuff. Bleu de Chauffe really leans into that, maybe better than anyone. Most Rugged: Saddleback Leather Flight Bag If the main reason you like the idea of a leather messenger is because it makes you look a little more like Indiana Jones… as Belloq says in Raiders, "you and i are very much alike." What I Like Distinct, antiquated design and Gladstone opening make the Flight Bag beautiful and unique at this price Functional: lots of pockets (and hidden pockets) Well built, with high quality leather, hardware, and thread Thickest, heaviest leather I've seen 4 colors available Stridewise writer and Saddleback superfan Troy Barmore snapped this pic on a trip to Europe. Paris, I think. Downsides But Not Dealbreakers Not subtle: this is a loud, confident bag Heavy at 6 pounds empty Internal laptop sleeve is loose and floppy Sometimes $599, sometimes $629, it's the priciest bag on this list Pigskin lining means it's not kosher or halal, if it's a concern Features / Specs Bristling with pockets, hidden pockets, buckles, and attitude The thickest, heaviest leather on this list 16" x 12" x 6" 5.5 pounds While I talked a lot about how many guys prioritize subtle, low key, minimalist messengers, you might want one that’s more evocative. And Saddleback is the old-timey adventure bag company Heavy, buckle-bound, and ideally suited to plundering Peruvian temples, the Flight Bag is not for the faint of heart — or the light of wallet (it's expensive) — but it's very good at what it does. Well designed to repel the elements and pickpockets alike, your valuables can be secured beneath buckles or a sneaky false bottom — or you can access items quickly in the hidden slip pockets behind those big pockets. https://www.youtube.com/watch?vd7MW4eEHWgg Price Currently $599, but I've seen it jump to $629. Some bristle at such a price, especially for a bag that's made in Mexico with chrome tanned leather. It's true that many purists prefer vegetable tanned leather over the chrome tanned kind you get here, but it's still the thickest I've ever seen. Plus, chrome tanned leather tends to be more resistant to the ravages of sunlight and water. Wrapping Up If you're a guy who shies away from messenger bags for looking too bike messenger-y, this list should provide a few great options. All of these bags are suitable for most offices and many come in multiple colors and sizes. Maybe your vibe is minimalist, quirky, European, or archaeologist. Whatever your flavor, there's a bag you'll love that will probably last the rest of your life.