I recommend Thursday Boots. I work in medical sales, so I am constantly on asphalt or standing on hospital floors. Sub $100 dress shoes wear out in less than a year and aren’t waterproof for rainy/snowy days. I looked for a long time to find a dress boot that was waterproof and would work with a mainly business casual attire but could also step up to a suit on rare occasion.
AE, Alden, Viberg are all great but I have 4 kids, a mortgage, and am the sole breadwinner. Thursday’s met my budget needs at $199 and for what you get, I couldn’t be more pleased. Goodyear welted so they can be re-soled when the time comes, well crafted, and good leather quality.
I got these:
www.thursdayboots.com/products/mens-brown-captain?collection=boots
They have slip on Chelsea style also. They run about a half size smaller than tennis shoes.
I am very frugal and spent almost a year doing research, reading reviews, and even watched a video of a shoe cobbler taking them apart and discussing how they compare to more expensive brands before I took the plunge. Sad I know...but I am convinced that for a new shoe/boot, you cannot beat their prices for how well they are made. YMMV.