1. If you would like to go for the 'over-sized' look, make sure what you are buying is not actually over-sized in the sense that it is a few sizes too big. There are actual items that are made in the 'over-sized' style, so that they are tailored to fall a little longer or bigger in just the right places for your specific size- and those are the ones you should be buying.
2. I would also encourage everyone to avoid buying too many 'trendy' items and stick to buying items that are more resistant to changing times, such as a classic black pencil skirt, one good pair of black shorts(like the one Olivia is wearing), a well fitted blazer, etc. because these items never go out of style!