I had these very old bootcut jeans in the back of my closet waiting to be DIY-ed for years. I am the anti-pack rat and get rid of clothing that I don't wear or that doesn't fit, so it was meant to be that I saved these two sizes too big, out of style jeans! I knew I wanted another pair of boyfriend jeans, as the one pair I do own are light blue and are pretty distressed. 
Super unflattering and too big! 
STEP ONE: Mark your jeans where you want to cut them. I wanted the bottom of the jeans to hit my shin a few inches above my ankles. 
STEP TWO: {Not pictured} Cut the bottom of the jeans in a straight line across at the place marked. 
STEP THREE: {Not pictured} Roll the cut-off portion to cover the frayed edge that was cut and sew to secure at seams. I actually pulled mine in a bit as well to eliminate more of the flare from the bootcut shape. Don't fear the sewing part--it's very easy with just a needle and thread. This part took me 30 minutes total for both sides.
STEP FOUR: Place the cardboard underneath the area(s) to be distressed to protect the other side of the jeans. 
STEP FIVE: Take a razor blade or exacto knife and gently move it across the area you want your jeans to be distressed. Gently remove excess jean fuzz that will ball up as you distress.
I distressed the pockets and both sides around the outer thigh and hip. I'm considering adding some more distressing, but it's better to take it slow if you're not sure how much distressing you want.
 
TA-DA!

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