You're on!
And guess what? I have ACTUAL outfits worn for almost exactly the same situations a year ago!!
First, the theatre. I actually wore this twice, once to the theatre in Stratford, Ontario, and then later to a rainy night off-Broadway show early last July (though I think I had different footwear and a colourful cuff bracelet that time, plus an umbrella). The kimono jacket and peplum top were nods to last year's trends. The peplum is actually a knit, so it is soft and comfortable to sit in, not stiff.
Overall, my goal was to be comfortable sitting, standing, and walking fast; to be warm enough in cool air conditioning, but not too warm out in NY's humid air, and to look current and "with it."
I wore the cotton dress outfit in June to my aunt and uncle's 50th wedding anniversary party. It was held in a house, not a seniors' residence, but the event called for a not-too-dressy yet "dressed up" look, one that would be pleasing to a group of conservative older folks. My thought here was that they would appreciate the classic cut and the pretty colours. I was right.
I wouldn't wear the first outfit exactly as shown this year -- I'd want to make it more 2014 somehow, probably with a more fluid fit top of some kind, maybe with a different topper. But the tube skirt is a fab invention that can take you from the pub to the theatre without a hitch.
ETA: My main warm weather "strategy" last summer was colour blocking. It was a really easy way to give an outfit cohesion, especially when I couldn't add a topper (which often does that job to an extent).
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