The Converse aren't "waterproof" persay although Converse does make several water-resistant converse styles (mostly in a mid or high top-- google pointed that out to me). However, I find that in my monsoon environment that a good leather sneaker with a bit of Dubbin or other waterproofing leather condition applied will keep my feet dry crossing the parking lot so long as I don't step directly into the very large puddles or the river running down the street and "swamp them" where I have lots of water coming over the collar or tongue. I like the Cons because they have less "fluff" inside the tongue and side walls than an adidas or similar alternative and since the Nike takeover tend to have better wicking components, which means if they get a bit damp in my carelessness they dry much quicker. I haven't tried this pair, but I'm hoping they will be the replacement for a pair of Tigers that went to shoe heaven when I was purging before I moved this spring because they were done for. I may be unusual in this aspect, but I've never been sqeamish about getting my leather sneakers wet . . . probably because I treat them similarly to how I treat my non-weatherproof leather boots, which I protect and then have worn on plenty of mildly snowpacked and wet days when snowboots, docs, etc aren't called for. Otherwise I never would have had an opportunity to wear them! I wouldn't treat loafers or pumps like this since the leather and construction are a bit different, but I've even been known to wash leather sneakers in the washer. Sneakers only last two or three seasons for me anyway, because the insoles and soles wear out (mine are in heavy rotation, since I work somewhere where they are the preferred footwear for comfort and safety reasons). Some of that may be due to my climate since the humidity comes and goes with the rains, which may mean I have fewer issues since things do dry. In my search for sandals (since my other pair this year is tan suede, and I'm not doing that in the rain) I saw that Blondo also makes a variety of "waterproof" shoes -- if that is a brand that fits, I would check it out
https://www.zappos.com/waterpr.....roof+shoes. They make a closed toe espadrille, loafers, slip on sneakers, etc.
Your summer faves sound lovely-- I purchased a pair of wide-leg linen pants on a whim and have been loving them (feels like the best sort of PJs and I'm tempted to buy a second for lounging on my balcony) but agree that although I love my bootcut and flare jeans and the wide legs, it creates an "issue" when it rains, unlike my skinnies that I can roll, or a crop.