Autumn/Winter, I don't bloody think so.. I go out in a t-shirt and get weird looks in winter, can only imagine a girl in those XD Would probably look cute, I don't see any issue with a girl in jeans tho.
Super cute. Definitely have a high-end, expensive look to them, even if you get them at a thrift store or a cheap shop online.
I'd probably wear them with a pair of one-color pumps, with no ankle strap or anything to show off the legs and make 'em look super long. On top, I think a super bright patterned shirt would look great, especially one that ties in the front.
Leather shorts definitely give you the excuse to wear crazy jewelry, like thick chain necklaces or really dangly earrings. Fedoras, if you're into them, also look super great. :)
I thought the link would be of something slutty, but those actually look really cute. With the brown ones I would pair a floral top (preferably in pink or aqua) and with the black ones, I would wear a red top with either a black leather or denim vest and a long, clunky necklace.