I'm just past 50 and play with guys much, much younger here in LaLa land. For singer-songwriter music, pop, rock, americana, etc. just wear streamlined versions of classic stuff, just basic items. Things have to fit right, or get 'em tailored. The fit is as important as the style. Jeans should be slim, and tapered/rolled up at the bottom(sorry, no bootcut or piles of extra fabric down around your ankles--looks sloppy), shirts are slim/tailored and not Seinfeld puffy. Don't tuck them in or at least do it kinda casual and loose, so as not to like you're a waiter or in 5th grade getting your yearbook picture taken. Something as basic as black jeans that fit right, a denim work shirt that's slim, not baggy, with sleeves loosely rolled up, and some kind of cool worn-in looking classic work boots or classic sneaks(like classic Chucks, Vans, Allstars, etc.--no old man comfort walking shoes) does the trick for many genres. Plus, it's stuff you can wear every day. Go with the classics I say, but make sure it fits right.
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