Very clever and thoughtful post, Maneera! Many thanks to you and smart Suz. I'm one who finds white jeans too chilly-looking on my pale Winter self, so that moment of wearing them for the first time, like the first swimsuit outing, is a bit traumatic. I like all your suggestions, and will add that wearing a top that I really love (great color, happy associations, etc.) helps me, as does a loose, light oversized jacket or cardigan, worn open.
Years ago, when I did costumes for a small repertory theater, our lead actress in Star Spangled Girl went through boyfriend trouble and a sudden weight gain. I had to change her costume mid-season to maintain the illusion that she was an Olympic swimmer. A Speedo tank (red, white & blue stars of course) under white jeans and a loose, open white boating jacket worked--just!