Rugged/waterproof dress boots?

[BlkCfvy]

I’m a musician and I play a lot of wineries and outdoor venues in the spring through summer. We have to load in walking through grass, gravel, and sometimes mud or other things one may find in a field. I’m looking to upgrade from just grabbing a pair of cheap shoes from Ross or Target to get trashed in the muck and just buy some shoes or boots that will shrug off the gunk and will hold up like my regular dress shoes. Any recommendations or favorites?

 

[Crispyj]

I’m a musician and I play a lot of wineries and outdoor venues in the spring through summer. We have to load in walking through grass, gravel, and sometimes mud or other things one may find in a field. I’m looking to upgrade from just grabbing a pair of cheap shoes from Ross or Target to get trashed in the muck and just buy some shoes or boots that will shrug off the gunk and will hold up like my regular dress shoes. Any recommendations or favorites?

I like Heschung Ginkgo boots ($600 ish), not sure if that's within your budget though.

I also have a pair of wingtip boots by "Rush by Gordon Rush". Got it at C21 for $85? Worn in through 3 Syracuse winters and 2 NYC winters, barely took care of it and it's still doing well.

People would generally recommend Thursday Boots and Meermin around the $200 price point, but I didn't have a really good experience with either of them. I bought a pair of chelsea boots for my sister from Thursday Boots and the soles worn out pretty fast, like within a year the heels were noticeably shot. Meermin shoes are stiff and if they don't fit you perfectly, they are going to hurt your feet and it's not worth trying to break them in.

Allen Edmonds have a sale going on and you can get some boots for $200, quality should still be decent.