Comfortable Low Cut Boots

[ColM]

Looking for a low boot that is more along the line of a high top trekking shoe terms of comfort but with the looks of something like the Alden 403 (the 405 is too bright for my taste) or White’s Semi-Dress boots (which I currently have and are heavy and stiff as hell). Would prefer leather, but I need waterproof so maybe something with a GoreTex liner, whatever. Objective is waterproof all day comfort with a classic look.
Any help appreciated!

 

[AeroFan_07]

https://freenotecloth.com/collections/boots

They have several options.

How long have you owned the Semi-Dress? Have you done a "PNW-break in" with these?
Once fully broken in they are very comfortable.

This is from Nicks - same basic boot, but shows the correct way to break in these boots...
https://nicksboots.com/blog/post/how-do-i-break-in-leather-work-boots/

On edit - I read your original post a little more closely. Honestly if you can do with less "classic" looks, you might like the Adidas Terrex models, I use a pair of these quite often when the weather turns wet/icy/snowy and grip in icy conditions is very important to me. Falls are not fun! Here is one of the many models they offer: https://www.adidas.com/us/free_hiker

 

[Jasonissm]

Goretex is not durable, that will be the first to go and then you will have a shell of leather that's perfectly good to go, while the liner is completely destroyed, either broken down with friction or delaminated. If you need Goretex, then go for a light modern hiking shoe, if you don't need that level of water resistance, to be honest I don't think it will do much for a low top shoe unless you wear it with a gaiter, because water is still gonna get through the top and into your socks.

Regular welted leather footwear, if gusseted is perfectly adequate for most situations unless you're really spending hours fully submerged in water. I wore boots in heavy downpour that were gusseted, for about 2-3 hours, the only water that came through was through the stitch holes. That was the only time water got through while I wore them frequently in rain, if you work where you're always in water though, then maybe the Nick's Waterworks boots are more suitable, those are designed for people who work in very wet conditions and require waterproofing for very extended period of submersion. I would consider your use case, because Goretex although a great membrane, I don't think it pairs well with leather considering the lifespan of the materials being so different.