Ask the MB -- Chuck and Frank
A: Stick to Penguin for clothes and avoid their footwear; and definitely avoid the Chuck Ts as you hit 40, unless you're either John McEnroe or entered into a Dee Dee Ramone look-alike contest.
Franks fully pass muster for 40-somethings in our opinion. First, their roots are from the hardcourt; you rarely if ever see Frankenclydes at the skate park. Second, Puma has done something smart by introducing luxury Frankenclydes like this pony-hair version (which we've mentioned before a few times). They're fairly expensive, quite difficult to find, and will hold up well to 20-something scrutiny.
Say, for instance, you run into a Frankenclyde-wearing lad and you're in a pair of these. No words need to be spoken but here's what you're communicating: "Yes, you are wearing cool shoes. However, we both know that mine are cooler. I am your style and disposable income superior. Have a nice day."