Red Wings are lovely and the quality is clearly evident. I’ve owned their moc toe and chukka boots, however they take a fair bit of breaking in. The other downsides are the soles which are useless on snow, and they’re not properly waterproof.
Timberland’s 6″ boots are waterproof, insulated, and the soles grip well in snow, so a better winter option. Their earth keepers are nice too, however the soles on the version I owned weren’t as grippy as the classic 6″ Timberland’s and I found they wore down fairly quickly.
Timberland also have a higher end brand called Abington which are really nice, they’re made with high end vintage leathers and cost around the same as Red Wings, although again they’re not all waterproof and not as good in the snow (if that matters to you). Owned a few pairs of these, although always got them for around half price in the Xmas sales.
If you want a really nice pair of boots, (and have deep pockets) Yuketen are meant to be great.