I've had shorts that were too small. You don't want the chamois to be taut - that will chafe just as much as shorts that are too big.
They should fit like a second skin. Like pantyhose. Some women get along fine with men's shorts - if you can wear men's jeans, then men's cycling shorts will probably fit you fine, and vice versa. Personally I'm not even CLOSE to being that shape.
How snug you like your jersey is more personal preference. They'll flap if they're too loose (all over or just in places), but some people prefer that to a snugger fit. Different brands are different lengths, so you should be able to find a woman's jersey that fits you if you want one. PI jerseys seem to be extra short, but I don't really know which brands are extra long.



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