I got into a debate not too long ago with someone similar to my age (26). We discussed if there was an age limit to wearing sneakers such as Vans, Air Force 1s and Chuck Taylors when a person reaches 30yrs old or older? I am an avid Air Force 1 collector and I can't see my hobby going away anytime soon. With that being said I know when and where to wear them, I usually sport them on family vacations, if I am hanging out with my friends or on casual errands and hang outs. I usually wear them with collared shirts and nice jeans. I occasionally wear graphic T-shirts with them and I usually try to match the shoe color subtly. I only get to do this when I am free and work on weekends. Work week I am dress for success (shirt, tie and slacks).
My rival however feels at a certain age someone should stop wearing sneakers completely and should always be dressed as if they are going to work or wearing some sort dress shoe or boots. It makes them feel more adult when they dress this way. Or fear of running into clients outside of work. To me if you're an adult you take care of your family, your bills and any obligations you have. Just because you dress a certain way doesn't automatically make you better than anyone else if you aren't handling your responsibilities.
In some cases I do agree sneakers shouldn't be worn to a nice dinner, a wedding, job interview or job fair or a very ritzy club event. Other than that why should one conform to what is a norm to some people and strange to others.