Yes, exactly, Suz! Angie, I do think it's tied to authenticity and genuineness, and I love Jenn's addition of playfulness and gracefulness, and how someone who is skilled can make what they are doing (wearing?) look easy. Again, I am talking about the benign usage of effortless, as Helena described.
Continuing with your example, Suz, and picking up with Angie's dog walking style: Angie walks her pups in her immaculate velvet pants, pearls, and beautifully tailored wool coat and this is "effortless" for her, in that she doesn't have to think about it too much--she's just going about her day--and she conveys stylish ease, confidence, and genuineness. Whereas for me, if I were to wear a similar outfit to walk my dog, it would definitely require a lot of effort and I would feel ill at ease and conscious of what I was wearing, if that makes sense? So that would not be "effortless" for me.
Lol, Carla :)!