I think 'looking good' has different meanings depending on whether or not someone passes. What does it mean to say that someone who doesn't pass at all looks good? Looks good as what - a woman or a well turned-out crossdresser? Stylish, good hair/makeup? Perhaps that's what it would mean in that particular context. Ultimately I think it depends on what you're trying to achieve, and that may differ between transsexuals and crossdressers.