I have been completely living in this dress from Toronto line House of Spy. I have it in a blue colour, and it is completely transitional, chic, and sexy. Plus it is amazingly comfortable, seriously. Like, comfier than sweats.
It has a deep v-neck (sexy!) but a loose overall fit (not TOO sexy) and adjustable drawstring.
With the string drawn short, I paired it with heels and some sexy drop-earrings for drinks at Ultra Supper Club on Queen.
With the string drawn long (it goes as far as halfway down my calves when let loose), I paired it with some plain-old havaianas and big shades and wore it over my bikini up north.
I bought it at Pho Pa on West Queen West. I believe they still have a couple in light brown/gray, and they're on sale now! Also available at House of Spy's online shop.