I got my Timbuk2 Messenger bag back in 2002 I think, before they had become popular, particularly in Ohio. Back then, they only offered the one bag in various sizes (though now they have a huge variety of bags), and the online bag builder had debuted a few years earlier. I custom designed my bag, skipping the internal divider, but electing to have the boot, padded strap, and laptop sleeve. (New options include the grab handle, and smaller reflector tabs instead of the flags.) The boot is no longer an option for the bags, but it's an extra layer of material on the bottom of the bag for improved durability. I got the bag since it seemed uber-practical, and being able to customize the colors on the website was huge. I loved the bag, and I still use it occasionally.
More recently, I've been using the Osprey Torque. While I wasn't able to custom pick the colors, the integrated laptop sleeve, grab handle, external pocket, and nice selection of internal pockets are all advantages it has over the Timbuk2. Unfortunately, it doesn't have the convenience of the velcro flap for easy access, and it's a semi-rigid bag, which has it's pros and cons.
Anyway, I've seen a few Freitag bags here and there, and I'd imagine by brother's comment about then being the new Timbuk2 is two fold.
- They allow customization. In fact, this is probably their main selling point, as they re-purpose old truck tarpaulins.
- While I'd say Timbuk2 has jumped the shark, Freitag is the bag for trendsters . . .
Other hipster bags of note could include Manhattan Portage, Chrome, and maybe even Crumpler.