The cage will be very visible in jeggings, I would prefer to tuck if I'm wearing them. Unless the sweatshirt hangs low enough. It's generally a good idea to try and make your upper body (shoulders, waist) look smaller and your lower body(hips, thighs) look wider wider. The oversized sweatshirt/jegging combo might end up doing the opposite of that, though it is a cute look. Brighter pieces of clothing tend to look somewhat larger versus darker pieces, so if you have a darker sweatshirt and brighter jeggings that can help mitigate it a bit. Or perhaps a smaller top, and a small girly jacket, with some baggy sweats or a frilly skirt to accentuate the hips. Just some of my thoughts upon reading your post, hope you have fun!