Angie, I agree with you about the spiky, unpleasant and even sometimes dreaded expression "trying too hard". This is a infallible freezer for anyone embarking the journey of discovering and defining their style. I put it in the same category as "too young for her age" and "too loud". It does however describe one reality we see around, although what it describe is the reverse of what it actually is.
Just as "Effortless" means actually effort, "Trying too hard", as Ruth beautifully explained, actually comes from not trying enough!
Looking at JA's picture, it occurred to me that a great part of her effortlessness is also due to all the care and effort put on the canvas on which these clothes will land. Besides the fact the actress is insanely fit, her body shape is respected, her skin is tanned, her hair colour is perfect for her skin tone, her hair must have taken time to style, her brows are done and done well, her nails are manicured, if she were to speak you would see her teeth have been whitened, and she walks elegantly with feet pointing straight. Not just that: the details are certainly the most expensive parts of her "effortless" outfit: her sunglasses are just the perfect size and shape for her face and must also be top of the line with top $$$$, her hand bag lands just at the perfect height on her side and I don't dare imagine how much it must have cost, the colour combination screams "I did not shop in a 'common' store where the only available colours are beige, black, blue and red" ... etc.
Well I am certainly not advocating we all should emulate JA and the unreal (and very expensive, time consuming) level of care she maintains for her bod. Looking at stars and the ease they seem to carry their clothes with is deceptive and depressing. Also, what credit do they have when they are surrounded by professionals and can spend any amount of $$$ and time on their looks? Do you think these stars are _really_ confident? I wonder what would happen if they were stripped of all this help.
I just want to make a point that for a style to be effortless, simply pairing one item with another won't do it. There is more to it underneath! However it isn't necessarily what Hollywood stars and pop culture pushes at us either. I don't think beauty can only lie in perfect teeth, tanned skin and skinny legs! The most stylish and beautiful women I have met have not fallen into this mould. Yet they are the ones who inspire me, the ones I remember. They cared for themselves. Their hair matched their shape, their styles, and flattered their eyes or smiles. Their nails were clean, filed. They smelled good. they paid attention to details.
This said, ButterflyLady, I understand what you mean in this picture about the _idea_ of effortless in JA's outfit. Even if completely fake in its making, the resulting image translates a feeling we all aspire for I think, when we go out in the world with our daily clothes, a feeling of being pretty no matter which direction the clothes fall, the feeling that we can confidently confront the world without having to pay the price of pain, energy, stress. Which we shouldn't, really, but unfortunately too often is the reality of women.