I come from a pretty poor/rough around the edges background. (As in didn't regularly have enough food, etc.). I am lacking the knowledge of how to appear more sophisticated/credible at the office. (FWIW, I'm an exec in the finance industry. My female peers wear high end clothing, louboutins, hair is curled, etc. Every day they do this!) My goals are to appear stylish, sophisticated, and edgy. And to be comfortable. I cannot wear heels.

I really feel comfortable in a kind of feminine tomboy type outfit. Ann Taylor skinny crop slacks, Johnston and Murphy cap toe oxfords, or black leather pointy toe runners. Tops and accessories have always been my challenge. I like keeping it easy... I'm thinking I should go with high quality blouses, like silk, in white or cream. And then I'd wear a blazer... Black Velvet, purple/black tweed with a moto cut, cropped black with a rolled up sleeve, etc. No idea how to accessories this look, or what else I should do to pull it together. Also, what I'm the heck do I do with my hair? I have a chin length bob with the left side shaved. Please send help