Interesting idea, Gaylene. I think it's largely true, although sometimes we need some unifying elements to bring the disparate bits together. I guess that's where the classics come in.
Yes, yes and yes from me on all three items you linked. Now I want that grey tunic too:) These are all that far removed from how I see your style Shannon. You are defiitely on the right track in my very humble opinion.

I'm feeling rather dense because I think the pieces you linked to and the jacket in Angie's pics would all slide into your wardrobe beautifully. The jacket especially actually screams your name to me. I can see it on you over a dress, or a column of neutral.

More fabulous thoughts!

Runcarla - you make a good point about the bandage dress. I do feel more comfortable wearing a blazer with it but I still see what you're saying.

Rae - oh you are sooo smart! Yep - if these were by Cleo or VC I would have them in my closet already. So what is it about a name then that makes a person more hesitant about owning that piece???

Gaylene - your friend is pretty smart. I do suspect that's quite true although as Suz mentions, it's making sure you tie everything in together to make the look "you".

Deb - thanks for the positive reinforcement

Traci - I'm crazy in love with the HL jacket that Angie linked to. But that's unfortunately not in the budget

Still thinking and pondering...
I sure hope so, Shannon, because I have the same desire to mix things up....and the same worries/difficulties as you, Suz, Ingunn, and others who've posted that they struggle with "how" to do this effectively.

Gaylene makes a good point about trusting your instincts. It's funny, but I have a painter/interior designer friend who told me the same thing: Trust your instincts. You know [what's right for you] better than you think.

Desire to mix things up is why I'm clinging to the style descriptor "elegant eclectic"....it covers a lot of bases and allows for a lot of deviation/experimentation!
Of course! Sorry to be late here. I do this all the time, often with footwear. Classic outfit plus RATE footwear. Some find this jarring, but for me it keeps me feeling like myself. And a HL piece is the perfect way to go, IMHO. The smoking jacket is very much like my Theory blazer and will go with everything.
Well I think I decided to give an item a try and I contacted all three sellers regarding specifics.

The plain grey cowl neck tee is no longer available.

The dress she states would fit anyone from a size 6 - 10. Well I'm a 10-12 so that's not gonna work.

The abstract pattern tee, based on the detailed measurements, will also be too small.

Poop. When I look at the HL item on the Nordstrom website, they list a large as being equivalent to a size 12. But I have the feeling that HL sizing just isn't going to work for me after all