Oh yeah, the Duck's in trouble. It's like the Hotel California, Very Violet. You can never leave!
I think pearls go with jeans and flannel shirts the same way diamond earrings do- the contrast is fun. But to me it's also touchy-feely and can go the wrong way, too. I usually wear some kind of pearls every day, and I just go with my feeling because who wants to go about feeling silly. I'm more likely to wear baroque or smaller pearls with my usual very casual clothes. And if I'm not wearing makeup or going anywhere, I usually just wear small pearl stud earrings. My style is pretty simple anyway, usually no more than three jewelry pieces total.
As per another earlier post, ha I had forgotten all about earth shoes. One way I can think of to gain confidence about what goes with what is to watch a reality TV fashion makeover show. I can't remember the names of any now but if you feel like googling it, you can probably find one. Just be prepared to cringe, though! It reminds me of those house hunting shows where I keep seeing my kitchen cabinets and such and some lil Miss Priss househunter shrieks and says she simply shan't live in such squalor.