How old is too old to wear leggings and skinny jeans? I just did a fashion show for the Geo Wives Club and most of my models were in their 50’s and 60’s. We put several of them in either leggings or slim legged pants, and they looked great! The issue isn’t whether a 65 year old can wear leggings. This issue is how to interpret the trend for a mature woman. First of all, we didn’t choose a slim silhouette unless it flattered the woman wearing it. In other words, those with larger hips and legs wore a-line skirts or looser fitting slacks. Those with slim legs wore leggings or cigarette pants and loose fitting tunics that came down to the appropriate length. About 90% of the models wore layered tops. A jacket and tank, for example, work well together to hide figure flaws while still showing off a waist. With some well thought out clothing choices, they were all dressed in the latest trends and looked classy, fashionable and perfectly dressed for their age.