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The Best Retro Bags Have Vintage-Appeal Without Sacrificing Practicality

The internet has made it so that many people can do their 9-to-5s from anywhere. What before would have been an entire desk can often be reduced to a laptop. But being able to work from anywhere presents its own challenges. For one, people can have a hard time separating their work life from home life if their office is anywhere they have WiFi. But on a more practical level, the work-from-anywhere lifestyle necessitates having a good bag.

A good bag needs to be able to accommodate your tech and daily essentials without slowing you down too much when you’re running to catch the train. There are a lot of stylish technical bags out there that appeal to the streetwear set. These bags will be made from modern materials like nylon and done in sleek neutral colors like black and gray. But if your style leans a little more old school, it can be hard to find a daily bag that suits your sense of style. Having a technical-looking bag when you prefer Red Wings to the lastest sneaker can create a mismatched look. But you don’t need to choose between the practicality of a technical bag and that rugged look you prefer.

We’ve rounded up a few of our favorite retro bags. These include single-strap cross-body bags,  messengers bags, and duffels. They’re cut from traditional-looking leather and canvas. Some of these bags have designated tech pockets for your laptops and tablets, and others just have a ton of pockets for easy organization. What they all have in common is their rugged, vintage look.

1. KomalC Leather Laptop Messenger Bag

If you want a bag with that rugged Filson look but you don’t have Filson money, this affordable leather bag from KomalC is a good pick. While it probably won’t last you as long as the premium options, it is made from genuine leather. Plus, the distressed look will continue to look good with wear. There are two front pouch pockets and one rear-zippered compartment. The main compartment has a center divider with organizers for pens and notebooks. The laptop compartment can hold up to a 15-inch laptop.

Pros: Rugged genuine leather bag, available in various colors like distressed brown and charcoal black. Has several internal organizers for keeping track of essentials. Detachable shoulder strap.

Cons: The shoulder strap is thin, and may dig into the shoulder.

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2. Leaper Retro Messenger Bag

This shoulder bag falls somewhere between a crossbody/sling bag and a traditional messenger bag. It comes in two sizes. A medium bag can accommodate a 10-inch tablet and a large can hold up to a 13-inch laptop. There are several side pockets that are secured using clasps or zippers, allowing you to securely stow your phone and wallet while still being able to quickly access them. The single shoulder strap is padded and adjustable, and there’s also a loop handle on top of the bag for carrying it in your hand. The main compartment has various pouches for staying organized.

Pros: Compact backpack that’s somewhere between a crossbody bag and a messenger bag, making it good for carrying daily essentials like small laptops. Has ample exterior pockets and internal organizers.

Cons: Mesh water bottle holder on the large bag tends to fray pretty quickly.

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3. Sweetbriar Classic Messenger Bag

Vintage and rugged doesn’t mean that it has to have leather. This simple bag from Sweetbriar is all canvas, and the simple design is perfect for a variety of uses ranging from a work bag to a supplementary bag for grocery shopping. It has a roomy interior compartment with a small zippered pouch for hiding small essentials. Under the main flap are two pouch pockets, and on the side of the bag are two water-bottle pockets. There are a few rustic colors like army green, olive drab, and tan. On the back of the bag is a small webbing strap for carrying in the hand.

Pros: Minimalist but rugged messenger bag for carrying a variety of essentials. It has a roomy main compartment, four discreet external pockets, and one internal zippered pouch. It comes in a variety of colors.

Cons: No zipper for main compartment and pockets, so internal items are less secure if the bag rolls over.

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4. S-ZONE Oversized Duffel Weekend Bag

Once you have a rugged day to day bag, you might want something that complements it for travel and weekend trips. This bag is made from a mix of tough canvas and leather details. There are a variety of vintage, earthy colors available such as khaki, coffee, and army green. The bag has internal organizers for pens and notebooks, and there’s a small zippered compartment on the outside to maintain easy access to essentials like passports and wallets.

Pros: Stylish weekender bag made from tough canvas and genuine leather. Various internal organizers and external pockets for travel and daily essentials. Detachable shoulder strap.

Cons: Color transfer may occur.

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5. Berchirly Retro Unisex Canvas Leather Messenger Shoulder Bag

For an easy everyday option, this bag from Berchirly is made from canvas and comes in a range of distressed colors. The bag comes in several sizes, and you can choose based on the size of the laptop you have. Options range between a 13.3-inch and a 17.3-inch laptop. Even the smaller options are deceptively large, and there are several pouches and pockets. The front has a buckle-style closure, but instead of being an actual buckle, it uses a magnetic clasp. That makes it more convenient than trying to undo a buckle every time you need to open the bag.

Pros: Good option for those with large laptops. The XL size can accommodate a 17.3-inch laptop, but you can also choose smaller sizes. All of the options are spacious enough for filling with multiple binders and books.

Cons: The bag doesn’t have a top handle, there’s only a shoulder strap.

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6. Komal’s Passion Leather Rustic Vintage Leather Messenger Bag

For someone who needs a simple and stylish bag for carrying a laptop, pens, and maybe a couple notebooks, this leather shoulder bag is a good option. It has one main compartment with a single divider for organizing your essentials. There’s a zippered pocket on the back of the bag, two buckled pouches on the front, and two small pockets on the side for small items like pens and chargers. Despite the minimal organization and slim profile, it expands to hold a lot of stuff.

Pros: Stylish and simple leather bag with a top handle, two front pouches, and several other small pockets. Made from genuine leather. A slim bag that can expand to hold a lot of items.

Cons: Thin leather and minimal padding, so it may be good to have a laptop case when using this bag as a laptop bag.

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7. BLUBOON Canvas Vintage Backpack

While there are many great messenger-style bags on this list, some people simply prefer a backpack. If that’s the case, this option from BLUBOON combines the ruggedness of a rucksack with the organization of a technical backpack. It has plenty of exterior-zippered pockets, plus a few internal pockets and organizers. The shoulder straps are adjustable and there’s a top handle for carrying in the hand. It comes in a range of rugged colors, too.

Pros: Rucksack style bag with plenty of secure, zippered pockets and internal organizers. Roomy enough to accommodate a 15.6-inch laptop.

Cons: The magnetic buckles are not the most durable.

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