Jay, I agree with you; it is useful and seems "friendly old geezer" approachable. I commonly wear a vest even when not out photographing, and tend to also wear t-shirts or sweatshirts with harmless/amusing themes like the Kliban cat or Far Side. And the vest may not be of the photo vest type.
Stewmander, thanks for the link to Scott EVest, an interesting concept.
Some of the vests have a large pocket either low on the back or mid-level. The latter remind me of the trauma plate pocket on the front of a ballistic vest. The iPad might help a little if shot in the back...
Sam, that Woolrich on eBay looks very similar to (a low quality) one I just wore out; I wonder if it's been discontinued, as I don't see it on their site. I'm about your size, so the XL one on eBay would be too large.
The more bulging with photo gear, the less stylish (or more unstylish?) the vest appears. But when out actively photographing, I think style yields to utility.
I'm a little surprised we're so style conscious about photo vests. I agree that substituting a sport jacket would bring it significantly upscale, and that's always an option too. I'm imagining Steve Jobs at a board of directors meeting. 🙂 But if you cram a lens and flash into its pockets, the jacket loses what style it had. Then one considers a bag of some kind, maybe like a courier bag, while other clothing sets whatever style you want. That does sound attractive. I like pockets, but I don't really like them bulging.
What I find attractive about vests is enough outside pockets for small items like filters, meter, film, SD cards, phone, hearing aids, kleenex, glasses, keys, etc, and an inside pocket or two for checkbook, wallet, notepad, the mail, etc. Maybe a small second lens. I mostly carry just one camera over a shoulder anyway.