So i gave in and tried this whole messenger bag thing,i got a cheap timbuk2 bag for around $60 bucks and i wear it super high on my shoulders and as tight as the strap can be,i see other people riding around like this but im curious,where the hell do you put all that excess strap from tightening it so much besides having it dig into your back under the bag,i know its a stupid question but im just curious what you guys do besides having a long flap of strap hanging off the side of you.

Oh yea,and how the hell do you get it to not pull down on one side of your shirt? it makes me look more ******** than i already am.

I wear mine (same bag) centered on the lower part of my back. It stays that way while I ride with the aid of the extra cross strap, and feels comfortable, shirt-wise and otherwise. I folded the excess strap up and secured it w/ a heavy rubber band, I don't notice it now.

EveryManALion,

Your problems stem from the fact your bag is empty. It's not really intended to be. I think you've seen other people carrying empty messenger bags. Lowering the bag will help with both your problems. You can sort of roll up and band the strap. Maybe a smaller bag would be good.

I wrap the strap around the cross chest part of the bag. Sometimes it can be annoying. I am going to try wearing my bag differently to change it up

I'm not sure about Timbuk2 bags, but usually you form a loop with the excess strap at the buckle. This generally allows you to quickly add or remove slack with one hand. I don't know if the Timbuk2 buckle allows you to do the one-hand thing, but I would think the same principle applies in terms of being able to cinch up your bag as your load changes. Here's a pic showing the loop underneath the left arm of the rider on the right:

https://www.flickr.com/photos/onezilla/537297262/

My bag has a mechanism for attaching the extra strap you pull through to tighten it, to the bag. Its pretty convenient. With all other compression straps and such I use rubber bands, zip ties, or twist ties to keep them under control. When its raining they always find a way to drip down the back of my socks...

I'm not sure what you mean about the t-shirt either. I don't have problems like this.

Also, life is a lot easier when you have things in the bag. When a messenger bag is empty it is a horrible thing to try to get it to fit right... especially if it is a large one.

yeah. timbuk2's are great if they're sized right for the load and you use the cross strap.

otherwise, you are kinda stuck with a bunchy shirt. i never do anything with excess strap loops. the newer timbuk2's(2010) have a cam buckle quick release, which is nice, but i don't know if their extra features will help your problems.

i got a kemmer bag chrome copy and it's so much better of a design that i sold my timbuk2 messenger and picked up a swig backpack. the backpack, aside from looking pretty huge on me and being difficult to access without taking off completely, is awesome- comfortable at any load and just as durable as a normal classic messenger.
but as far as messenger bags, timbuk2's are very hard to wear if they're not loaded in a particular way with the right amount of stuff for the size they are. and think of the fit like shoe laces... you can adjust them a great many ways but you have to find what's right for you for it to be comfortable and snug enough that it won't fall off.

i sold my messenger bag and got a backpack. i just could not take that single strap bag. they 'look' cooler but still backpacks are more comfortable.

Not for me.

+1

Depends on what im doing. Urban riding I use my Timbuk2 Classic Messenger but out on the trail, I carry a Dakine Apex backpack.

I lowered the bag so the strap was as long as i would ever want it... then cut off the extra and singed the ends with a lighter so they wouldn't fray. Then I looped it back through the binder by the buckle.
Without cutting, the loop was obnoxiously long.