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I have the 253 in Large. The reflective strip doesn't bother me, but I don't know how much it helps; I never used the light loop. The strap got too intimate with a space heater and 2/3 burned through. Was fine before that through nearly 7 years of continuous commuter (not messenger...) use.

The other bag is built to fit a small front rack, is not listed on their website, only used it for about two years now, but is holding up without complaint so far.

FWIW, if I was getting another bag, I'd be considering a backpack, and probably one not as pricey as any of the Bailey offerings, probably not mfg in USA...

I've kind of lived out of my old Timbuk2. Great bag, holds a lot, not H2Oproof at all. Just got a BaileyWorks Super Pro and it's a huge upgrade. The strap adjustment mechanism is just great. Great fit for me at 6'4". Haven't really put it to much serious heavily loaded use yet, so I don't know how much of an improvement it will be from my Timbuk2 as far as riding fit goes, but it certainly is an improvement.

I have a Bailey Works Super-Pro, my friend has a Seagull. They are both great bags. Seagull has tougher velcro (more like Chrome & Timbuk2), but I've never had any issue at all w/ Bailey Works velcro.

Seagull has the nice option of back padding. Bailey Works has the laptop sleeve, which can be added, and works the same way, + it carries a laptop.

Seagulls are more customizable, if that's something you want. Bailey Works, you just pick a color.

Bailey Works has a split-strap, Seagull does not (I don't think). It's a nice feature, but I never actually use it.

Bailey works has far more compartments. Bucket pocket, two outer bellows pockets, one with a small pocket + pen holders, one exterior side pocket next to the bellows (another can be added for $), inside, two side pockets (Think water bottles, tubes, tools), also inside, an open pocket (separate from the bucket pocket), and a zipper pocket. Seagull has the bucket pocket, two exterior bellows pockets, and a small velcro pocket on the inside. Nothing more.

Both handmade in the US.

Both have stabilizer straps. Bailey Works comes across your rib cage, Seagull comes a little higher, under the armpit.

Both ride well, cinched high & close to your back.

Bailey Works has reflective strips (at no extra cost). They do work well, and one is located on the bottom of the bag, which is the side that faces cars while riding. Seagull has no reflective strips.

One more thing- the only complaint my friend has about Seagull, is that the corner of the flap sticks up when closed, so it obstructs her view when she looks behind her to check for traffic. She remarked to me that she likes how Bailey Works "hugs" the body, meaning, it wraps around the shoulder more, and doesn't obstruct the view. I had never thought about it, but she is right.

That's all I got.