What an amazing discussion! I can't believe it led to A Pattern Language and Laura has actually consulted with the authors! What an amazing book and amazing story (and would I ever love to see your house, Laura!) Perhaps I'd better find another superlative than "amazing" before the trip, though.
Gryffin, I love your jodhpur leggings and your belts -- I remember you posted a few of the belts long ago and I have always like to imagine the way they light up your darks and also add a bit of subtle contrast -- the idea of a western style belt with a blazer and jodhpurs is such a fun and clever juxtaposition. I'll bet you look great in those crossover jeans, too. I love that style also and have been sorely tempted by it myself.
What an interesting question about wild cards/ shadow style. I found myself nodding along with several people's comments. I think on the whole I agree with Staysfit -- it's something the moves my style along a little bit and over time it tends to become incorporated into the style and does not feel "wild" any more. My most successful wild cards often (though not always) have an element of luxury, as Peri said. Part of what is "wild" is treating myself to something so nice -- but that is not the whole story because my Reiss blazer is definitely "nice" and luxe but did not feel in any way like a wild card. Some become workhorses, and some are only occasional wear. Many strike me as "fun" in some way, whether that be because they inject an element of whimsy in and of themselves (a conversational pattern, say) or for some other, less-easy-to-explain reason. And every now and then, a wild card will be something that seems almost out of character. I do have to send some of those items back before cutting the tags, though. My EF skirted leggings fall into that category. Bought a pair last year at NAS, tried to wear them at home to see if I could love them -- and alas. They are not for me. A wild card gone wrong.
A few examples of ones that worked:
My Rebecca Minkoff hobo, which was a wild card because I truly prefer a structured bag. But this one won my heart and I use it all the time!
My BR sequinned culottes. While I liked culottes from the start and could see myself wearing them, we were 3 years into the trend before I found my first pair, and those were a very fancy sequinned version marked down to $25! I bought them and love them, even though I wear them only twice a year.
My lilac cocoon coat is a bit of a wild card...the style is expected but the colour was not. It's a great winter brightener.
My new red crops are similar. I don't know how they will turn out.
My Club Monaco silk dress is not a wild card in the sense of style -- but it was a wild card purchase in that I fell in love with it when it first came out but could not justify the price given infrequency of need for this type of item in my life. But then I saw it on sale, and simply had to have it. I wore it more than I expected simply because I love it so much!
My silver crushed velour top is also a kind of wild card, I think! It's a bit silly, a bit fun, but also surprisingly luxe-looking with a navy blazer over top and extremely comfortable!