I'd say this first outfit is quite military inspired because of the detailing on the shorts and lace up boots, the colours are also reminiscent of this theme. Perfect for going out if you want achieve a smart look but wish to show off your tan at the same time.
This look is definitely focussed on the shorts rather than the shirt because of the bold print. Keeping the shirt and the shoes black focuses the attention on the shorts giving the look an overall summery vibe. The wedges make it more of a night time look but changing them to a pair of sandals or flats will make it perfect for the day.
This is one way I would choose to dress down the shirt; the distressed denim gives it a more casual feel whilst the boots add some edge to the look. I would wear it when I'm going out with my friends or even to do some shopping.