Timbuk2 has horrible strap designs. They're only decent as shoulder bags or for carrying light, flexible loads on an upright bike. In the drops, heavily loaded, on a road bike, they're absolutely awful.

I own a PAC Designs Ultimate which I regularly use to haul 20 - 30 lbs back and forth from work, in addition to hauling 40 - 50 lbs of groceries. The bag is absolutely amazing, but will run you around $400 with shipping from Canada. They are generally regarded as the best messenger bag on the planet, and you pay for that.

I've heard good stuff about Seagull too.

For hauling school-type loads, unless you want to buy a PAC along with the X-strap and waist belt (more money...), I'd get a Chrome Sultan backpack. Big, comfy, well made, lasts forever, and honestly, Chrome is the best bang for your buck.

Chicago Wig also makes a backpack, and they seem to have a good reputation, in addition to Reload and Timbuk2 (their backpack seems good, even if their mess bag are not).

Most people would just use panniers for hauling school books though. I don't like panniers, but I can imagine using them if my daily load was 40 - 50 lbs.

Bailey Works can be moved to either shoulder. The strap adjusts with a simple pull of a front loop, not sure about chrome, maybe it does the same?

One thing i've read about Chrome bags, since you're in school.. if you've got jokester friends, they might be tempted to 'test' that buckle release. I checked out the Chromes in the store and they look to be built pretty much the same as the Bailey Works as far as weatherproofing and materials. I almost got a Chrome myself, but I liked that fact that not as many people have the Bailey works bag, (i see mostly chrome bags in l.a.) plus the big reflective strips were a big selling point for me.

http://www.bhop73.com/pictures/sun.jpg

Just learned that my Chrome Metropolis can carry a Wii Fit in its box. ;)

Timbuk2s are still well made. One bag of theirs died on me after 6 months (Commute), but I beat the snot out of my medium laptop messenger for at least as long and other than stains it looks new. I know lots of people who have been using the same Timbuk2 bag for years.

My problem with Timbuk2 is that they are the retrogrouches of the messenger bag world. They seem to think that it's good that they haven't changed their strap design since 1985 or whatever, despite the fact that their straps are fundamentally unergonomic. Good companies like Bailey Works, Seagull, Zugster, PAC, etc., continuously update and experiment with different strap designs. I don't know about Chrome, but their straps are quite good and very ergonomic.

You can see that Timbuk2 doesn't get it just by watching their little animated "how to wear your messenger bag" thing. Their model wears her bag way, way too low, and probably too loose for cycling. Fine for walking around with, which maybe is the point since that's about the only thing their bags are good for...

Went for a twenty or so mile ride today with the Seagull black bag. This is my same school load, which doesn't even put a dent in the bag's capacity. The only time the bag moved was when I started bouncing from spinning the pedals too fast [~120 RPM or so...I am still a n00b to cycling for the most part], and even then it was because I was bouncing a little bit. The bag is far more comfortable in the drops than the Timbuk2.

I like the fact that the Timbuk2 is more organized, and it pretty well designed as far as carrying pencils, notebooks, small things, etc. I picked up a few organizational pockets from REI, and I am going to use them to keep the Seagull straightened out.

There really is no comparison between the two bags. The Seagull is a messenger bag; the Timbuk2 isn't. Great bag for wearing over the shoulder and walking around in, but not great on a bike. OK, but not great.

Two questions about the Seagull Black Bag: has anyone broken one, and what the heck will happen if I take a spill and land on my chest with that giant buckle there? Chrome is the same way, I think.

ok

I bought also this nice bag from REI

http://media.rei.com/media/t/1285646.jpg

It fits my lunch (not small) my dress pants, my shoes (size 13) my dress shirt, socks, etc ... and then its full

The thing i like is when i want to go fast on my bike it does not create that much aero drag.

Lightweight when empty too ...

my extra large classic timbuk2 bag has 4 times the capacity.

Both have their functions; but I wanted something smaller for going to work back and forth.

meow

The R.E. Load Deluxe is at the top of my short list for a new bag. They are really nice, I know a few people that have them. One guy has had Timbuk2, Chrome, among others and likes his Deluxe the best. Worth checking out...

http://reloadbags.com/bags/deluxe.php

If you're on a tight budget,Timbuk2. You can get mediums and larges on eBay for $50-60 shipped if you're not super picky about color. But if you've got the cash,Bailey Super Pro all the way. Awsome reversible strap,lots of room,lots of pockets,keeps rain out,very durable.

I used to have a Timbuk2 but didn't like the strap and how it adjusted. I then got a Chrome and love it. It easy to use, comfortable, holds a ton and has been super durable so far (had it about a year). The only downside with it (as others have mentioned) is that you can't really switch sholders. Not a big deal for me, but may be for some. I love it.

I got a medium black bag, and it's still fairly big. I use it for school and keep about 3-4 books in it plus a binder and it could definitely hold more. The first night I got it I bought $200 worth of clothes at the mall and rode home with it all in my bag, stopped at best buy and bought some ipod stuff and that went in there as well with 1 u-lock and 2 cables. The strap design they use is genius, it tightens and releases so easily, although the buckle was an eyesore at first it adds some character to the bag like the seatbelt buckle to chrome. Fits extremely well and was a very solidly-stitched bag, I'm extremely happy with it.

There's only 1 bag

http://www.demartinibags.com/

I still have mine from when Mr. Demartini was making them in Little Italy. You had to actually call ahead and tell him what messenger company you worked for before you picked it up. I had my friend call him and pretend I was him.

The original does not always mean the best.

That strap design looks unergonomic. Like a shoulder bag, which is what they were originally designed for.

You didn't say whether or not you want a built in laptop compartment. You might consider that in your search. Most of the above mentioned mfgrs make such a bag. FWIW I have the Timbuk2 with one and I really like it the dedicated laptop pocket.
Not sure I would get the Timbuk2 again. It's great quality but the handle ends up digging into my back and it's not exactly shaped to fit your back very well. Oh but once I had a large full bottle of water explode in there once and the outside remained dry...so I know it's waterproof at least from the inside!

I guess you've never rode with one for 25+ years and hauled a lot of stuff in it. The strap was the best thing. Nice and wide and it fit over the shoulder perfect. The heavy duty buckle is the opposite of what Timbuktu has. You can swing it around your front while riding and loosen it and get stuff out, swing it to your back and tighten it again.

The strap was long enough to accomodate very big and heavy loads and the entire bag sits right above your butt and just below your where your shirt would end. Really right in the perfect center of gravity where if you have 20 or more pounds of stuff in there, you really can't feel it cause its in an inert part of your back. If you pull on it and bring it up higher on your back, it really defeats the purpose of the design. Its meant to be ridden just above the saddle.

ooh. looks like dimartini wins. i want one.

I ride daily with a Chrome Kremlin (the huge one) and I've never had problems looking over my shoulder. I think it's really important to keep the flap strapped down tight, otherwise it can bunch up and get in your way.

Chrome makes great bags, though definitely not cheap. I lucked out and scored mine for $40 on eBay.

No complaints about my chrome. Only reason I chose it was because I saw a good deal on craigslist. It does get in the way a bit when looking to the left but I have never given it any thought as it is not obsctructive to me.

I don't believe that the minor differences between higher end bags warrant much thought - the only problem I have with all bags (except some of the suspension backpacks - might look into those but I am leaning toward panniers these days) is that they sweat up your back in the summer. Every other difference seems to come down to exclusivity, which I could care less about. So one material or clip or nylon doohickey is slightly more refined than another (a clip will perform for 20,000 openings/closings versus 25,000) - who cares?

This Demartini bag sounds like it works on different principles but I've no experience with it nor have I ever seen a bag worn in the way triplebutted describes and I live/work/go to school in NYC. I don't think he is making things up but this sounds like a trend of the past.

Chrome bags seem to be the choice of nearly every messenger here and the Metro seems to be the preferred size for most although a few other guys and I use the Kremlin which can carry an immense amount of stuff.

I addressed the issue of there being no back padding...

If you go to an outdoor supply store you can get camping rolls that are made of some very high quality and high density foam... I just happened to have an old one kicking around.

I cut a piece to size and slipped it between the liner and outer shell of the bag and it makes a world of difference in comfort when you are carrying a few bricks...it does make things a little warmer but that can also be good thing when one has to work / ride in sub zero temps.

I figure that one day I will probably pick up a Metropolis.

That addresses what I don't like about carrying heavy or dense loads in the Chrome. It's most secure high on my back, but it's not high enough to lift loads above the small of my back -- which really starts to hurt after a while. Shifting them further back and down like you mention would really help a lot.

Chrome Messenger Packs
 

After casually following this thread I decided to visit Chrome's site. I don't think there has been a mention of their Messenger Packs; http://www.chromebags.com/products/bags/packs/ Seems as they would be a more comfortable option because the weight is evenly distributed over both shoulders. After spending six years as a wagon messenger I know time is money and the single strap bags are easier and quicker to get in and out of. Anyone have experience with the Packs? I could use a large bag for shopping trips.

I currently use a Osprey 700 cu. in. pack that works well with a 3L CamelBak bladder; http://www.ospreypacks.com/detail.ph...ab=description For short or sporting trips. When a little cargo room is needed I go to a North Face Exuinox with 1850 cu. in. that is discontinued and available at REI for a very good price; http://www.rei.com/outlet/product/773360. Nicely padded but no hydro sleeve.

I can only look at the guys I work with and see that among the 20 or so full time messengers here, one uses a chrome backpack and the extra time he might need to get in and out of his bag is made up for the fact he is also a Cat 2 racer.

My boss also prefers a backpack over the sling as he says it is more comfortable and even more water resistant.

I think it all comes down to preference and what one has to carry on a daily basis... if I am travelling light I don't use my Chrome bag but prefer a small rock climbing bag.

Upon further review their Roll Top Packs; http://www.chromebags.com/products/bags/show/31/ Make even more sense for me. Dual straps, padded back and exterior pockets. But the $, ouch!

Freight Bags ftw! They run large..be aware!

Did you check out a pannier that converts to a backpack when you get off the bike? They are more expensive than a simple pannier or a simple messenger bag, but it's really worth it to invest in the perfect bag so it doesn't become a PITA. :)