I have a pair of old redwing moctoes, they're wonderful and the moc toe boot... The new ones are supposedly still made entirely like they were in the past (but some other redwings are not quite the same as they used to be.... like, I heard the iron rangers use some more synthetic linings inside now).

Mine are the classic 875 model. If I was buying them today I'd get the 1907 model which is a bit wider and more comfortable. Well, they're practically moulded to my foot now and are very comfortable, but I'd like a bit of a wider sole regardless, The 875 are very narrow.

For less than the Redwings, you can check out Thorogood, those are really nice too (I think just slightly inferior materials). Also Thursdays are great boots for the money (compared to the redwings they have slightl. inferior materials and made in Mexico...).

Above Redwings, you need to look at pacific northwest boots... Whites, Nicks, JKs, Wesco, Franks...

For 50$, or even 100$ (with inflation...), Solovairs/classic Docs would be awesome. But UK mass production is gone and labour got way more expensive, while the iconic style of the Docs also has a price now... That's why I think Jim Greens are awesome, sure they won't get as classic as Docs but they do offer amazing quality for what they cost.