I don't have this exact skort but a couple of similar ones. The closest is a cargo skort from Terry, which has a wrap around front like yours. All my skorts have the thin mesh short underneath. So far no embarrassing events. The skorts really seem to stay put, I don't feel like they are going to blow open when a breeze hits or as I peddle. However, when biking I can see the leg of the shorts as I peddle. But I don't think they are noticeable enough to be too worrisome. Even so, I don't always use the included shorts. Sometimes I use thicker stand alone shorts and they do feel more "secure." I use the mesh liner shorts a lot under regular shorts or pants.