Cool and rumpled is the way to go - middle age style for men

I'm beginning to think that cool and rumpled is the way to go in middle aged style. It shows self-confidence and, more importantly, a feeling of comfort in one's clothes. However, it could also suggest slovenliness unless done very carefully.

Don't overdo it, as it could look too studied. A linen suit will achieve the affect naturally and without artifice. Or simply sleep in your clothes for a night. All these pictures are from the Sartorialist.

Rumpled, dishevelled, untidy, scruffy, tousled, mussed up, messed up, messy, disturbed, ruffled, jumbled, topsy turvy, disarranged, discomposed, disrupted, disorganised, disordered, disarrayed, broken up, in a shambles, slapdash, slipshod, cluttered, chaotic, confused, sloppy, slovenly, unkempt, unfastidious, bedraggled, ungroomed, unpolished, grungy, rough, creased, neglected, shabby, bedraggled, tacky, etc etc.