The kind of person I usually see wearing a shirt like this (though I haven't seen this exact one) is a very young woman, often a teenager, who wears it as an act of rebellion against parental and/or social strictures that are keeping them from expressing themselves as a sexual being. At least that's how I would like to read it. It does worry me, however, as a symbol of such, as it often is paired with naiveté and careless behavior.
I find the phrase particularly problematic as someone who is enjoying reclaiming the word "slut," but have no desire to claim the word "shame." I'd rather reclaim the "walk of shame" as a "walk of whoo-eeee I had great sex and I'm still glowing from it," or something like that.