WP Standard – formerly called Whipping Post Leather – makes rugged leather bags, totes, and briefcases and their Rucksack is one of my favorites. Designed to look like something a Pony Express rider would slip on for a visit to town, this $275 is sturdy, handsome, and ages surprisingly well.
There are some trade-offs, however. Except for two small front pouches there are no hidden nooks and crannies in this spare 15×15 inch sack. The main compartment can fit a laptop and a few notebooks and the front pouches can hold accessories like mice or a little collection of plugs. There is no fancy nylon mesh or gear organizers here, just a brown expanse of full grain leather.
I wore this backpack for a few months before writing this and found it surprisingly comfortable and great for travel. Because it is so simple I forced myself to pare down my gear slightly and I was able to consolidate my cables and other accessories into separate pouches. I could fit a laptop, iPad Pro, and a paperback along side multiple notebooks and planners and I could even overstuff the thing on long flights. As long as I was able to buckle the front strap nothing fell out or was lost.
This bag assumes that you’re OK with thick, heavy leather and that you’re willing to forgo a lot of the bells and whistles you get with more modern styles. That said, it has a great classic look and it’s very usable. I suspect this bag would last decades longer than anything you could buy at Office Depot and it would look good doing it. At $275 it’s a bit steep but you’re paying for years – if not decades – of regular use and abuse. It’s worth the investment.