One of my favorite looks when pairing jeans with booties is the half cuff. It's an effortless look and is fun when paired with an oversized tee and sunglasses for a weekend with friends. Tip #4: To make this look as effortless as possible, don't make your half cuffs match. Keep them about the same height, but roll/cuff them at slightly different angles and widths to make them look effortless and a little haphazard.