Are these boots good for wet weather?

They are cemented-construction leather boots with a lugged outsole, so grip on wet pavement is decent. The cemented build and leather upper are not described as waterproof, so heavy rain will soak through over time.

What is the outsole made of?

A foamed combination outsole with visible lugs. That means a lighter, cushioned feel underfoot than a solid rubber sole, with the lugs giving traction.

Is the lining leather too?

Yes. Both the upper and the lining are cow leather, which breathes better than synthetic lining but needs the same conditioning and care as the outside.

How do these compare with a plain leather ankle boot?

The wingtip perforation and lugged sole make them more decorative and more casual than a plain leather ankle boot. Choose these for the brogue look; choose a plain pair for a cleaner, dressier line.

How should I care for them?

Wipe off dirt, let them dry away from direct heat, and condition the leather periodically. Store them with shoe trees to hold the shape of the toe and the wingtip panels.