My BF is also in his 50's and not the most trendy dresser, although I'd definitely say he is stylish. But, yeah, no skinnies, no blingy pockets. He is quite slim with a 31/34 pant size, so many jeans don't fit in the legs or butt. We tried on over 20 pair a year or two back before we got him Citizens of Humanity jeans at Nordstrom. Jagger bootcut and Sid straight legs. No crazy washes or whiskers. Not the cheapest at around $150, but soooo much better than the Levi's he wouldn't wear anymore because "they are just too uncomfortable and stiff."
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