Oh, Nancy, thank you SO much for raising this subject! So near and dear to my heart. I am going to be reading along here with great interest in the hope of discovering some helpful ideas. Already the insights and questions are prompting some thoughts.
You know something? The woman whose photo you posted actually looks quite a lot like you, not only in superficial ways (the blonde hair, the slender build) but also, and more importantly, in what she is wearing! So maybe you are closer to that artistic style than you really believe. Still, I know what you mean. I think you and I are both attracted to classic looks, you with a bit of boho/western; me with a bit of retro/vintage thrown in. The boho/western and the retro/vintage were probably our way of trying to inject a bit of personality into our outfits, but it's not always easy to figure out how to do that in a way that feels coherent when your main inclinations are towards classic, tailored looks.
Isabel, you raise a really good question, I think. Just what does it mean to express oneself through one's clothing, and why would it be (or seem) important to express one's artistic leanings, in particular?
Here is my take on this:
First, just as with any other profession, people have certain expectations of artists. You would be shocked and a little uncomfortable, probably, if your lawyer or accountant showed up to a meeting wearing distressed denim and or a lamé dress; so, too, it's a bit disconcerting to see an artist dressed in a business suit. Many artists do appear in public (for openings, readings, performances, etc.) or even for teaching. And even artists need some credibility—within their own profession, and with the wider world. Clothes can be help to categorize us. And that, in turn, can make others more comfortable with us.
Next, there's the question of comfort. Painters need to work in clothes that can get dirty. Photojournalists need to wear footwear that lets them get around. Writers sit at desks, so in that sense they are more like office workers...but their desks are usually in their homes, and they need to consider that in creating a wardrobe that satisfies their needs.
And then there is the question of self-perception. More than most professions, perhaps, artists need to believe in ourselves...because the world, in general, does not believe in or care about artists. (I am not speaking about present company, of course!)
Here is the thing: artists work very long hours, often on top of regular paid jobs, in order to produce work that is usually rejected many times before it receives acceptance. In fact, many artists work their whole lifetimes without being "seen" or accepted as artists by the outside world.
And even if they ARE accepted by a group of peers (this in itself usually takes up to ten years of unrewarded work), there is very low likelihood that they will be financially compensated very much for their work. Society does not value this work in the way it values the work of doctors or lawyers, for example.
That's not a complaint. It's just a reality. And what it means is that sometimes it becomes very hard to have faith in what we're doing or even to believe in our own identities. What other work requires such acceptance of constant rejection? Or the ability to deal with questions like, "Oh, so you're a writer...why don't I know your name?"
Which in turn makes it feel important, somehow, to SHOW who we are. We are showing ourselves as much as the world. Buttressing our sometimes fragile sense of identity. Clothes are a kind of armour.
And yet another reason is that they are a kind of play. We want to have fun!