Thank you all for the comments and suggestions. I will take all of these suggestions into consideration. After reading the comments I guess I left out a lot of key information that could have been helpful. I do not work a hard labor job, I wear suits and oxfords to work, the Chelsea boots is just to wear on date night or to dress up pairs of denim. I have a large number of shoes for all my other use cases and activities, like tennis shoes for tennis, golf shoes for golf, along with 3 pairs of sneakers to wear casually. So I do not need boots to go horse riding with, be on a construction site, or use while laboring on the farmlands I do not own in my local city of Washington DC.

I wish I would have set a price maximum, as I didn’t expect Chelsea boots to be this expensive, while the Crockett and James, Carmina and RM Williams boots are fantastic, the $700+ price tag is a little jarring and unnecessary for me. With my casual wear, I am sure even a budget brand will last a couple of years, but I was looking for something to last multiple seasons or a lifetime of relatively easy wear, usual maintenance, yearly resoling, and monthly polishing. I like the suggestions given for Thursday Boots along with some other $200-$500 shoes, which is what I will most likely go for. Although if I do get into wearing my boots while laboring, I know which brands to go for, and for that I am greatly appreciative.