Waterproof, breathable socks, booties, shoe inserts, and footwear assemblies containing the shoe inserts are provided. The booties and shoe inserts include a laminate of a seamless ePTFE membrane and at least one textile. The bootie is conformable over a range of sizes and shoe shapes, and may be shaped to fit numerous sizes and shapes of asymmetrical shoe lasts. The bootie may shrink to fit, or, alternatively, be stretched to fit, an asymmetrical last having a desired size to form a shoe insert. Such a conformable bootie eliminates the need to have multiple sizes of shoe inserts correlating to particular shoe sizes. In embodiments where the ePTFE is seamless and continuous, the shoe insert eliminates the need for a waterproof seam tape, which is conventionally used to make shoe inserts waterproof. Methods of forming the socks, booties, and shoe inserts are also provided.