Hey, I like them both. Personally, I love the Church's/Barker style of shoes (I have a few pairs, which I wear regularly), and I actually think they can look very well with jeans and/or khakis and a smart shirt, or t-shirt and say, linen or leather jacket. Besides, good well-made shoes - even good formal shoes - can actually be extremely comfortable once they have been broken in.
Basically, the first one is extremely stylish - and thus, a bit more formal. To my mind, it's the sort of thing you could wear to a cocktail party, formal launch of something (book, movie, play whatever), I'd see it as evening wear, wheras the second, although still 'smart', is a bit less formal, and so could probably be worn to a wider number of venues and settings.