I work in the fashion industry and call tell you point blank, NOTHING IS TIMELESS. 501s have lost tons of market-share, and the unwillingness of Levis to change their business strategy away from this style has resulted in a business teetering on verge of extinction
when was the last time you heard of high fashion coming out of JC Penney, Kohls, or Sears? Take your 501s and burn them. Three major problems exist in the 501 design. 1. Tapered leg. NEVER BUY TAPERED STYLES This results in making practically everybody look shorter and fatter then they really are because you are adding volume to the top half of your body and reducing volume from the knee down. Tapering only helps individuals who are underweight or slight in build. Straight-legged styles create balance between the top and bottom halves of a man. If you are barrel-chested or have a belly try loose fit straight leg jeans, the wider you legs appear the slimmer your upper body will appear. 2. High rise. These jeans will say natural waist, or sits at the waist. They sit at the navel and do not flatter the front or the back; in fact they create a much larger backside than is necessary. 3. Stonewashed. This is a style that says i'm old and out of touch. Im not saying that you have to run out and purchase jeans that have been splattered with acid or destroyed by sanding or even whiskered. Im simply saying if the style says Stonewashed PUT IT DOWN and WALK AWAY. There are other styles, and a sales associate or consultant should be able to steer you towards jeans that are for a mature man that are not crazy and too youthful, but distinguished and updated to current trends. An updated pair of jeans can easily make a man look 5-10 years younger. Go down to the GAP or Banana take a look at the Denim Wall and try on a few different fits and styles
if your store has unisex fitting rooms dont be afraid to walk out of the room and ask another customer, especially a woman (theyll know if your ass looks good)
walk around in them
and dont get hung up on sizes
take a few sizes in with you some bigger some smaller
but remember you have to take time, like a good half an hour to an hour