Quote Originally Posted by Mabouya View Post
Bumping this with a semi-random comment/question:

About 15 yrs ago my workplace went from dress shirts & pants + ties to casual (jeans, Dockers, polo shirts in summer, etc.) so now I can wear shoes that are way more casual. I've gravitated to stuff like Sebago Docksiders (with dark sole, not the white).

Here's the issue: I've also found that for me shoes with somewhat squishy soles and heels are way, way more comfortable for walking than the old dress-shoe plain leather soles, or the harder rubber casuals. Unfortunately, I've been having a hard time finding a brand / model that is consistently available. When I visit my sister in Maine we often swing by LL Bean and I can sometimes find something good there, but when they wear out I check the web site to get another pair and that particular model is gone.

So, what's your go-to comfy Topsider/Docksider?
For domestic type things, look at Eastland's Made in Maine, Rancourt, and Quoddy. I think all of these are resolable, too.

you can catch the Quoddys on sale at Brooks Brothers every once and a while.

Hording is also an option if you find something you like.

for a shoe that is more dressy than this, you might want to check out some of the new orthotic shoes from Allen Edmonds. Looks like they have a softer vibram type sole. Tricker also makes some like this, but you have to be committed to the shoe game for these.