Mid-90s. Among other things...
baseball cap, most likely Tigers or Yankees, mostly forward, with generous curving of the bill
tee-shirt, at least 2 sizes too large
flannel shirt, unbuttoned, also very large, sometimes with sleeves rolled up
wide-leg, JNCO-style jeans, often with large holes in the knee, sometimes with flannel pajama pants underneath, up to 6" too large in the waist
braided leather belt, too big so that the end would hang to mid-thigh