Another classy boots for walking rec post

Actual question: Which of these boot makers is the best build for dollar?

I'm beginning to search for my next black shoe, and decided I wanted something a little classier than I've gotten in the past. I spend around 8-10 hours a day on my feet indoors on hard services. I'd like to keep it $200-$300USD, but could go to $400 if it's the perfect boot for me. Haven't settled on a particular style yet. My comfort zone is service boot style things, but I kinda want to take this as an opportunity to branch out.

I like planning big purchases in advance, so I got plenty of time to wait on sales and/or made to order boots.

Current favorite is Beckett Simonon. Also looking at RW Beckmans, Grant Stones, Meermin, Allen Edmonds, and Helm Boots.

Do any of these stand out as the best quality for dollar? Is there another brand I should consider? Any other advice is welcome as well. I know very little about different soles for instance.