For the teacher, when school starts, summer is officially over. The calendar may still acknowledge additional days of summer, and the weather may still be balmy (I’m fanning myself on a humid evening as I write this), but it’s fall. That’s all there is to it.
When I shop for work clothes, I don’t shop for summer clothes. I have a much larger wardrobe for winter than for summer. The best pieces I have are transitional, and I find myself looking for pieces that will go from summer to fall with a few tweaks.
Last year I bought a skater dress in grass green, and now I have one in teal as well. I’m kind of obsessed with this as a transition piece, since you can wear it on its own or with a small shrug in summertime, or with a sweater or blazer in fall. A bright solid is perfect for late summer and fall, as it doesn’t seem too frivolous or summer-y. You can wear this dress with sandals in summer, knee-high boots as the weather gets colder, or flats in a bright (not necessarily matching) color anytime.
When it comes to skater dresses (or fit and flare dresses, or a-line dresses–whatever you want to call them), you really can’t beat ModCloth for selection. I love that site so much.