It may seem odd to put a dressy jacket with casual shorts, but I really like the contrast between the two. It dresses up everyday shorts and at the same time allows you to wear your blazer as something else besides the typical pant suit look.
This is a nice outfit to travel in because it's comfortable and the jacket can be worn if it becomes chilly.
I love how Nicky takes three closet staples (white t-shirt, jean shorts, and a black jacket) and adds a fun pair of shoes to create a look all her own.
Roll up the sleeves of your jacket to make it more modern and less stuffy.
Experiment with different texture fabrics, such as tweed, to accommodate your personal style.
And if you're brave, try a jacket with a length that hits the end of your shorts.