Leather Laptop Bag

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if you want a messenger bag, get a real messenger bag, not a leather briefcase with a flap and a long strap. It will be uncomfortable. Take it from someone who commutes to work on a bike and often carries a laptop. A couple I suggest are:

https://trakke.com/collections/waxed-canvas-messenger-bags/products/wee-lug-messenger-bag

https://bedouinfoundry.com/products/barbary

neither are leather, but are waxed canvas. Which is a lot better if it might get wet.

A leather satchel like others have recommended is fine, as long as your realize it’s just a briefcase/satchel with a strap.

Absolutely best advice here. Also my experience. Those beautiful leather satchels/briefcases made to last 100 yrs are not really made to be regularly carried hanging from your shoulder, they already weigh a few kg empty and those straps... well, I spent a little fortune on shoulder/neck massage until I saw the light of cross-body design and got one of this:


https://www.wardow.com/es/chrome-mini-metro-bolso-de-mensajero-bg-001-bk-es-0.html
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My Saddleback items are nicely made, but leather is heavy. I travel with a Saddleback duffle, and it gets a lot of compliments, but it's a burden to lug around. (And what does it say about my vanity that I still travel with that same duffle?)
 
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Absolutely best advice here. Also my experience. Those really beautiful leather satchels made to last 100 yrs are not really made to be regularly carried hanging from your shoulder, they already weigh a few kg empty and those straps... well, I spent a little fortune on shoulder/neck massage until I saw the light of cross-body design and got one of this:


https://www.wardow.com/es/chrome-mini-metro-bolso-de-mensajero-bg-001-bk-es-0.html

yeah, Chrome makes a good bag as well. The straps and position of a true messenger bag make all the difference.
 
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Couple brands that I'm partial too for Briefcases are Hex Bags (More budget) and Killspencer. The killspencer bags above the price point you listed but if you want something to last 20-25 years that's gonna come at a premium. I dig the aesthetics of them but some may not be too keen. Some of their bags are outfitted with mil-spec hardware and I can attest that the build quality is wonderful.
https://killspencer.com/collections/briefcase/products/utility-attache-briefcase?variant=44538091726
utilityattachebriefcase1.jpg

https://killspencer.com/collections/briefcase/products/briefcase-3-0?variant=41316189798586
Briefcase_30.jpg

This, though is my day to day:
https://www.hexbrand.com/products/n...ase-black-ripstop?_pos=1&_sid=1e840e85e&_ss=r
HX2551_BKRP.jpg
Not leather, but the exterior is a water resistant poly rip stop. I use it every day going to construction sites and client meetings and so far after four years it's still holding up.
 
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My first post in a while, I have a Satchel & Paige Counselor, very well made, and is holding up well…
 
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I own this leather briefcase from Von Baer. I've had it for 2 years now, and I've been extremely pleased with it. It's good-looking, well-crafted, durable, and ages really well.
The leather is premium and has handled daily wear like a champ. It's the kind of leather that gets better with age. The stitching and hardware are also of high quality, which reassures me that it's going to be with me for the long haul.
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This is just under a year with my Waterfield SF bag. Zero complaints.
 
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Found this one in a charity shop this week.
Nice find! The previous owner probably had to have rotator cuff surgery after carrying that for a few months.
 
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Nice find! The previous owner probably had to have rotator cuff surgery after carrying that for a few months.
Yeah, very heavy indeed.