Thanks everyone for the replies. I ended up going to s local boot store and he sold me on a pair of Red Wing Ely's. They fit perfect and were decent priced with a lifetime warranty/repair pass. He does in house repairs so i can go in there and get a sole glued back on or whatever the case may be for free. They are the mosy comfortable boots ive had and they arent even broke in yet.
I tried a pair of Red Wing flexbonds but didnt like them at all due to how skinny they were and the wire lace system felt corny to me lol.
Thanks again!
Bonus pic of my old Keens:lmao:
https://postimg.cc/gallery/DGKtRgS
On the next go-round consider a goodyear-welt boot - the ones that have the sole sewed onto the uppers. In most cases a new sole can be replaced on the existing welt, but it can be removed and a new welt sewn on to completely restore the boot.
The bonded soles on the Ely can be replaced, but not indefinitely, and they do wear out. You also don't have any options on a replacement sole - it has to be the same one in order to fit. With a goodyear welt you can choose from a variety of soles to suit your use.
And an all leather boot is obviously much more durable than one that has fabric panels and trim. Good price for those Ely's, the moc-toe work boots tend to run closer to $200. Sometimes you can find factory seconds on ebay for a lot less - I've gotten a couple of pairs that way, my moc-toe Briar Oil Slick ones were about $150. The Briar Oil Slick leather is simply awesome - just re-oil to restore, amazing.
I think I got my Iron Rangers in oxblood the same way and they're awesome boots - more for style than work, although guys do wear them for certain applications. Unfortunately these are over $300 a pair, I think I paid about $250-$275 from an ebay seller.
For daily wear I really like the work chukkas, I work in an office. I've had a couple of pairs for several years - they are so comfortable and just last and last. I've resoled both with darker soles - I think they look better than the white crepe soles they come with. These run about $200-$275 a pair depending on the style. The original 595's you can only get at a retail store are simply awesome, under $200 when they're on sale, and just super comfortable.
A really cool guy in LA puts out a series of youtube vids on restoring boots - Brian The Bootmaker - check 'im out if you have interest:
https://www.youtube.com/c/BrianTheBootmaker
Red Wing Boot Company has a nearly cult-like following. Old American quality that is so rare these days.