Thank you all for your thoughtful replies. It's interesting to hear that for some of us, like Bijou, "statement" items tend to become surprise workhorses. Whereas for others it is more likely to be something closer to a wardrobe "essential."
For me personally, it's split between statements and essentials. I don't expect all my statements to become workhorses, but some of them do turn out to be. Recent examples the scarf and top in Finds. But a lot of my workhorses are "trendier" or "more current' versions of my old favourites. Those might surprise me in the way Gryffin describes. I might worry initially that they aren't quite the thing I want, but then their workmanship persuades me, or the slight difference turns out to be a huge benefit, either practically speaking or as a way of evolving my style in new directions, allowing me to see the beauty in some of my older pieces (in new combinations) etc.
Christina, good call on returning that (admittedly fun!) shirt. Same to you, Fashintern. The right suit will appear when you need it.
Janet, Staysfit -- both your purchases fall into the broad category of items you typically love to wear (jackets, jeans) and in each case find relatively easy to fit (jeans for Staysfit, jackets for Janet). They sound like the "evolving your style forward" items that become workhorses in my closet.
Suntiger, I can imagine burnt orange being a real winner for you!
Cardiff Girl, I use that strategy too. I walked away from booties without trying on, and bag (though on sale) and went home and thought for a few days. They were still in mind so I went back to investigate more thoroughly. I tried on. I bought.
LaPed, Fashintern -- I'm curious about this "things I'm supposed to like" comment. What does that mean? Things you feel you have to buy to fill certain holes, but never really like?