Re what to wear with different style jeans, I tend to wear all of mine with oversized tshirts, button down shirts and chunky knits.
On feet, I wear my skinnies with Chelsea boots, riding boots or wellies. They're the best jeans to wear in the rain as they can be tucked into boots. Don't care about style in the rain 
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I wear my girlfriend jeans with white trainers or brogues and no show socks, as they have a turn up and show a bit of ankle.
I wear my flares with trainers, high tops, brogues or sometimes boots on the inside. Great for colder weather, as they go over shoes and I can wear long socks underneath.
My boyfriend jeans only seem to look nice with a fitted shirt, jacket and brogues. Otherwise, I just wear them slobbing around the house in my slippers! But theoretically, I could wear them with any shoes as they go down to the ground. I might even try them with heels one day, though I hate heels generally (can't walk in them) and only own one pair, (a hangover from my office work days), as a result.