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If I'm going out in the evening and don't want to carry a big pannier bag or rucksack, I keep my lights and whatever else in a small 'man-bag'. It's like a smaller version of a messenger bag: about 20 x 15 cm on a shoulder strap. I try to keep it towards my back rather than under my arm, to stop it swinging around, but invariably it slides out (especially on right-hand bends) and towards my front. If I leave it, it dangles under my chest and rubs on my knees as I pedal.

What can I do to keep it in place? I've tried shortening and lengthening the strap, and I've used it nearly empty or quite heavy, and it doesn't seem to make a difference.

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You could probably use a carabiner and hook one side of the strap to your rear belt loop. – Kibbee Mar 27 '13 at 21:03
I tried the over-the-shoulder bag and never liked it (and still don't understand why they're so popular with cyclists.) I use a backpack or a mid-sized saddle bag with no issue. – WTHarper Mar 27 '13 at 21:18
This question is not what I thought it would be about, from just reading the title. :) – Neil Fein Mar 27 '13 at 21:59
@WTHarper I much prefer my panniers usually, but if I'm going out drinking in the evening they're a bit of a millstone to carry. – Dan Hulme Mar 27 '13 at 22:06
@DanHulme If you are confident in your style, a fanny pack has the same sort of on-the-go style but doesn't intrude quite as much as a backpack. However, you will be made fun of... – WTHarper Mar 27 '13 at 22:15

At the beginning of this video:

it looks like this bike messenger has an extra strap for his bag that comes up under his left arm to stabilize his load. Looks pretty neat, like it can be easily unsnapped to get the normal messenger bag access, and possibly be DIY-able.

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A lot of messenger bags have a strap specifically for this. Timbuk2 calls it a cross strap and even made a video showing how to use it. – Drew Stephens Mar 28 '13 at 14:20

Instead of adding an additional stabilizing strap as suggested by @obelia, you could wear the bag like a fanny pack, around your waist. I'm a big fan of this solution, and I proudly sport my fanny pack (or waist bag/ hip bag) on the regular. In addition to solving your over-the-shoulder-sliding dilemma, it also has the added advantages of 1) no sweaty back, and 2) no uneven wait distribution on your shoulders.

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Leave it at home.

Those bags are such a pain and not worth the effort. There are plenty of cool looking backpacks out there.

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Got to agree. Unless you need that messenger style access, backpack is all around better. But backpacks are not as cool as messenger style bags right now. – obelia Mar 28 '13 at 16:39

If it's an over the shoulder bag with no stabilizing strap coming up from under your other arm, it's not a suitable bag for carrying while riding a bike. You could always go the DIY approach and attach such a strap yourself, but if you'd rather not then use a different bag that's more suitable.

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