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Debate: Should a 49-year old guy wear jeans for walking around town with loafers/mocs? If so, what brand, cut, etc?
Agree with all the above. There's no reason you shouldn't wear jeans when you're middle-aged. I'm 36 and have no intention of stopping - I wouldn't know what the hell else to wear. But like other parts of your wardrobe you are better off getting something classic and simple and that suits your body type. Maybe avoid the more overt back-pocket stitching (or avoid it all together). Get them hemmed if necessary. Match with a Paul Smith shirt - can't go wrong I reckon.
Debate: Should a 49-year old guy wear jeans for walking around town with loafers/mocs? If so, what brand, cut, etc?