Decently distressed jeans are, somewhat counterintuitively, sparing in their ripeness. Distressing needs to look like years of wearing, not something mapped out on a cutting table in a few hours – placement is more important than quantity. Rips dead centre down the knee can look promising, but real wear and tear along the thigh where a seam would naturally split, some weird little ragged spot catching the light instead of gaping abrasively like some Medieval torture device, those things speak intention. Large gaping holes that look like they were drawn on with a children’s clown marker and stacked on top of each other tend to feel costume-y and pseudo-rebelbish, which is your first filter.
The denim itself needs to perform as well. Stiffer denim or something that’s on the heavier side of cotton will hold its shape around tears instead of ballooning out into oblivion after two wears, and will age better instead of slouching around your knees after three weeks.

Too much stretch and your distressing will recede and grow with wear, which is one of the quickest ways to look worn out instead of worn in.
My favourite pairs live somewhere in the middle.

Stiff enough that when you first put them on you can actually feel them conforming to your legs over the first few wears.
Cut is where you can get fussy or you can walk. Straight legs or something faintly relaxed through the thigh and calf allow tears to fall open naturally without constricting across the tear itself, which is where slim-fit jeans usually lose the fight against themselves, pulling holes wide and angry when they were only supposed to look lived in. The right rise, sits right at your waist or just comfortably below it will make the whole outfit feel intentional.
A soft sweater or an immaculate white shirt, tucked in to keep the jeans looking sharp will provide enough backbone that rips provide texture instead of looking unkempt. Boot or sleek trainer will keep you street-ready all day, but throw a sharper jacket on and slide into heeled boots and you’ve got an outfit that can take you into night time territory without needing to change at all. They’re great for those catch-all occasions that need a little grit without needing to be too dressy. A concert, a low key dinner, a long weekend binge – anywhere that rewards a slightly worn out finish.
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