Distressed jeans require a specific kind of confidence to wear convincingly because the deliberate damage to the fabric is the most obvious thing about them and that obviousness means the rest of your outfit needs to be doing something credible enough to contextualise it. A well distressed jean in a good straight or slim cut with a clean simple upper half and decent footwear reads as a deliberate casual choice. The same jeans with a similarly chaotic upper half and neglected footwear just looks like everything needs replacing. The quality of the distressing itself matters too. Good distressed denim looks like it happened through wear. Cheap distressed denim looks like someone attacked it with scissors and sandpaper which is because that’s exactly what happened and it shows. We’d look for something where the fading and wear looks authentic rather than manufactured and keep everything else clean and minimal around it.