Speaking as a just-turned 57yo, I have no self respect and so I spurn Jock Wan’s well-intentioned advise and wear jeans. However, I avoid spurious logo’s, stitching, pockets, buttons, flaps, embroidery, rips, etc, and stick with regular or loose fit, dark blue indigo denim. I’ve got several old pairs of Oakley jeans, one well-worn pair with a flannel lining which are perfect for winter, several pairs of Howies including a pair of their indigo dyed Tom Proof riding jeans, and a couple of pairs of my new favourite Uniqlo selvedge Japan Denim jeans, which are a brilliant fit and really comfortable. And cheap. Did I say cheap? You do have to watch the size, tho’, as others have said. I take a 32×34, but I tried some regular Uniqlo in their London main shop, and couldn’t even do the damn things up, so I took a chance and ordered a pair of 34×34 selvedge when they next arrived in the online shop on offer, and they were perfect, in length and waist. And no logos to be seen anywhere, just a small number on a leather waistband patch.
The old Oakley’s only had logo rivets, and the Howies only have the little stitching detail on one pocket, which I rather like. I’ve also got three Uniqlo flannel shirts, in different weights, which are bloody marvellous for the money, really soft and comfy. My new favourite jacket’s an Alpha Industries CWU45/P NATO issue pilots jacket, again, not a logo to be seen anywhere, just a Velcro patch on the chest for a name patch. Not even a logo label inside. Really anonymous. It is fireproof though, which might come in handy one day.