One of the investments I am looking to do this season is in a classic cropped jacket that I can wear all the time this fall/winter. As my mom loves to point out, jackets are the best investment because they are the first thing people see you in on the streets and you will probably wear it more than whatever you are wearing inside. So I figured that a smart classic cropped jacket would be a good choice- they are versatile and very chic.Something a little more edgy, we have this very stylishly tailored cropped jacket by Helmut Lang (who else?, left) and this printed jacket by Milly (right). I LOVE this jacket. This is my favourite cropped jacket of all because the bold print is still versatile being black and white and the feminine cut of the neckline brings edgy and girly together. It makes a statement and is still very wearable. I can totally see myself living and breathing this cropped jacket this season!