I LOVE the idea behind this, but the blazer is too short/small IMO. If you are going to do chucks with dress pants, I personally would only do leather, just so i can ensure they are extremely clean and white. When dirty, they will deteriorate your overall look.
Man! This is the same look as always…We get the picture of what you like. I do not: Jacket is too short and it seems that it cannot be buttoned, and the whole look is not “fresh” enough to wear chucks (or any other sneakers)