I don't dog walk but will weigh in on the shoes a bit:
Cons run a bit big so go by fit and not by size. Hard if you can't try in person I realize.

I have some similar Payless Champion slip on mary jane type (mine don't have a strap) shoes that I used at work in early morning running around, jumping up and down ladders, moving around merch before customers type of thing - they are really comfy. I like my slip on Pumas too. But i couldn't hike in those as I'd be afraid I would step in a hole or something and not enough grip on top of foot to stay on.

You might check consignment stores for nearly new non white footwear. I have found the best deals on gear - seems people buy nice stuff and then a year later discover it unused and consign! I have seen hiking shoes, new running shoes,etc. We have some stores around the Bay Are that specialize in used equipment and gear so you might check for those in your area too. Maybe a light hiking shoe is what you need instead of a cross trainer or runner?

Good luck with your furbaby - you are lucky that he found you And vice versa of course.

Fern - thank you for that link! I was looking at her blog the other day, but your specific link helps a whole lot.

I still didn't order any shoes quite yet, but no matter - just wore my ugly, practically neon white gym shoes. It was suggested that I try practicing on the leash in the backyard at first, if necessary. It was raining off and on all day and I had a ton of things on the go, so I took Gus errand running with me, and then when we got back we did some 'leash training.'

It was a good thing it was just in the backyard - he managed to squirm out of his collar (I'd forgotten to tighten it back up as per the Sharpie marker line we put on it the other day, specifically for this intensive leash training).

Gus is very challenging, but like I said - he has come a long, long way since I adopted him. This phase (be nice on the leash in the city) is just the next step. In any case, I'm pretty sure that at least half the problem is that I'm just too "nice" - making cutesy noises at him all the time. I can't say, "Gus, c'mon you big lug..." in a soft voice and expect him to listen.

I had a minor 'aha!' moment today - I thought it was kind of peculiar that my self esteem has been in the tank, and that I somehow ended up with this dog that needs me to be strong, tough and determined. I have a funny/eerie feeling that this is one of those 'meant to be' things.

I put on my (tacky white) gym shoes, my ancient old jeans, one of my gym shirts, a gym jacket, a ball cap (it was raining out there) and we did drills. No, I didn't look all that ....and Gus wasn't too impressed. He wriggled out of his collar after a few rounds of close/loose-leash training, at which point I remembered to tighten up the collar to the sharpie marked point specifically for this purpose and we started again...and when he realized he wasn't going to be able to wriggle out of his collar, he decided to fling himself on the ground instead. It really was funny, in a 'you had to be there' way. We practiced the leash walking for a good hour, and he did quite well after all (well, after a few shenanigans).

In the meantime, just wanted to say he is a very good boy, and that this is the final hurdle - going on walks where he has to stick close to me and behave in the city. He's *great* off leash and has learned so many commands. On the leash he's pretty good, but...the issue is that when he sees another dog, he lunges and gets all 'tough guy'. Being almost a hundred pounds, this isn't so easy to manage.

Ack! Once again, I've veered way off topic.

I have a crazy schedule right now, but I'm definitely going to get some (hopefully stylish) city dog walking shoes (thanks to everyone's great suggestions) with good arch support and a bit of grip on them.

...and Gus will learn to walk nicely in the city. Eventually.

This is off-topic, and I have to admit I always stop short of precision response when it comes to training with my dog, but when we were working on our heel - well, my dog is very short. I got a longish wooden dowel stick and a plastic end cap for it, which I'd smother in peanut butter. I held the stick down in front of the Lilypup to reward/lure her into the heel position.

Oh and yeah, the Lilypup *does* know when I'm just babbling and am not committed to enforcing a command. LOL.