Until recently I had always considered the shirt to be an item for the office - All stiff and buttoned and collared, not to mention, who would want to iron a shirt for the weekend?! But over the last few months I've had an absolute 360 change of heart. There is something so casual cool about having a collar peek out of a knitted jersey or having the bottom half-tucked into a pair of jeans. And if you roll up the sleeves and layer it under something, the burden of ironing then becomes optional!!
To keep it comfortable I would go for oversized and cotton and (while I'm probably stating the obvious) always team with pants or a skirt!! Oversized shirts are NOT the same as a shirt dress. I know this because once I actually tried to wear an oversized shirt as a dress and failed miserably. I thought I looked so FAAARRSHON when in reality I probably looked more like Tom Cruise in Risky Business (there's a good reason he does that dance in the privacy of his home). Thankfully I had good friends who told me to change before the shirt went public.
So, now that you have a clear example of a "Don't", please see below for some amazing examples of "Dos".
Images: Vogue Australia, Shine by Three, SNOB fashion blog, TheyAllHateUs.