Okay, I've been thinking about it all day, along with trying to find and recapture the indoor black kitten who slipped his harness when we went out to enjoy the sun and took off under the neighbor's fence. 5 hours later we found him, whew.
He's such a graceful, charming, rogue. That's it!
I think I have some overlap with Hil and DonnaF's ideas. When I've worn clothes that make me feel most 'me' and strong and centered they are:
Graceful - often a sleek silhouette, movement of skirts or scarfs, love draping, shoes that are easy to walk with a stride in. Can be sexy in an understated way. Tends toward simplicity, minimalism, and celebrates the lines or movement of the body. Color is harmonious if used.
Charming - there is a playful, confident, open aspect to the clothes. Graphic tees, some color, clothes are flattering and make it easy for me to strike up conversations with people. I can have in-jokes with my clothes that only I'm aware of. There can be a feminine charm quality, or an androgynous/handsome charisma.
Rogue - Can be UWP, can be a modern space cowboy, but can also be a Regency highwayman or Corinthian Earl who loves racing his matched pair. Style icons include Han Solo, Mal and Zoe from Firefly, Jim Morrison, a young Jamie Lee Curtis, Starbuck from the new BSG. So in practical terms embraces both historical and modern influences. Also Rogue in terms of stylistic freedom and mixing and matching. Can include an unexpected item, or contradictory impulses or break rules as long as the effect is charming and graceful. Encourages clothes to contain a little bit of excitement or the unexpected/unusual.
ETA: after some drinks and a really good pasta involving steelhead and shallots, I'm adding Grounded:
which is code for balanced, stable/strong/enduring, roots in the earth, practical, well-crafted, carefully and judiciously considered, often made of natural materials, considers sustainability/environmental impact .
I'm not the kind of charming graceful rogue that is a cardshark and will swindle you of your money, I'm the kind that is secretly reliable, down to earth, a good steward of the land and her investments.
ETA2: hmm... I also want Edgy/Contemporary there as an aspirational style.