I agree 100% with Marlene.
So much of this is very individual and context-driven. Personally, I am always conscious of the balance in this style issue because my life is very casual but I also strive for an element of sophistication, even on many of my most casual days. I don't need to worry about a professional appearance most days, but honestly, looking professional has never been a challenge for me. I learned office dressing at the age of 17 for my first part-time job (in a real estate office) and have always been one to err on the side of being "more dressed up" than my peers.
I *feel* like I pull off the ultra casual thing because of the details:
- graphic tee: usually a band that I truly love (Wilco, Old 97s, National, etc) so I think it avoids looking too cutesy or "ironic"
- jeans: try to keep them current and good fit, roll the hems, etc.
- hoodie in cashmere or a great-fitting denim or leather jacket with current styling (mixed media, great color, scrunch the sleeves, etc).
- casual shoes in a current or modern classic style - Cons, boots, etc. looking forward to the new slip-on sneakers as a fun option.
- details like a great, high quality belt, a current bag or clutch, and a signature piece of jewelry, which for me is usually a statement ring.
I don't think I'm delusional that I'm an almost-50-year-old wearing an ultra casual outfit like this. Part of why I share details of my life here is so you all understand the context of my style. I trust you all to let me know if I misstep.
But I digress -- back to you, Dana! I think you have your style nailed, and if you feel like something needs adjusting, I think you only need tweak some details. Honestly, I think sometimes we all get a little bored with our usual uniforms, and a little shake-up in the form of a new item or new remix can spark our creativity.