The best way to rip your clothes to make it look intentional and fashionable is to rip it in areas. Do not over rip up a piece of clothing, it will look like your dog tried to eat it. As shown in Jess's shirt, she decided to make small holes near the hem and at the shoulder.
I love how she paired it with the combat boots, makes it look casual, cool, and trendy.
Another way to wear this look is to layer things under the holes. Try wearing lace tights under holy jeans or leggings. Or wear a patterned shirt under a hole-y shirt. The possibilities are endless!