I do love that suit, Shannon. It is classic, but with subtle modern proportions, and you would look beautiful in it. I'm in total agreement that items like this, that seem like "outliers," are crucial to growing style and having fun with fashion.
I've been mulling this over a lot -- part of the reason I read, but didn't post on your last thread about spring items. I know I should only need a little refreshing, but there's a good portion of my warm weather wardrobe, particularly my "high summer" clothes that I'm not excited about wearing again.
Last year, I was experimenting with doing "super casual" summer looks well. I think it was largely successful, introducing new silhouettes with BF jeans, for example, but I don't feel quite "myself" when wearing those outfits todays. I could easily replace 1/4 of my spring and 1/2 of my summer closet......I'll have to write for a "style grant!"
This year, just like you, I will look for a trend or two to embrace that stretches me a bit and allows me to play with, say, a shadow style. Most of my funds and effort, however, will go to furthering my sense of "personal" style -- dressing in a way that seems to reflect my own body, complexion, lifestyle and tastes, and incorporating the trends into that goal, rather than vice versa.
I still resonate with retro dressing, particularly Kate Hepburn trousers, turtlenecks and soft shirts (although a different color palette), but I'm finding "clean" versions of these silhouettes impossible to find in RTW. The retro look of a few years ago is quite different --- more focus on details than "architecture" and silhouette, if that makes sense. I'm not interested in anything that might read as "twee," although I like those looks on others. I'd love more fluid fits, and I'm interested in adding one or two full midis to my spring/summer wardrobe, along with some pants with beautiful drape, both tapered and wide leg. I think I will get closer to the outfits I have in my mind if I get out my sewing machine again --- surmounting the issue of time and space!