Fashion crisis: shoes

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So...am I too old for the shoes on the left?  Too young for the ones on the right?

I recently bought a pair of Adidas similar to these (canvas, rubber toe cap, no "CAMPUS" on the side, but very similar otherwise).  I like them, I wear them, they are actually comfortable, and they happen to look great with jeans or beat-up khakis (which are the only kind of khakis I own...primarily because I don't want to buy new pants).

But am I too old for them?

I personally hate seeing people my age ("my age" is late 40's) wearing clothes that they obviously had a teen-age skateboarder pick out for them and I laugh, thinking "why are they wearing that?!?".  (And of course don't forget the mid-40's pizza delivery guy we always get who wears hoodies, tight black (but still sagging) shorts and sockless high-tops...but that's another post in itself.)

But now I'm thinking I'm approaching that age where I can't wear what I used to.

But what can I wear?  I own cargo shorts; are they OK?  Half my life is spent in t-shirts and shorts; does that meet with public approval?  Ironically this is why I miss Eddie Bauer stores: they seemed to specialize in clothes for the 30-50 crowd (which may also be the reason why they aren't around anymore...nobody likes knowingly being targeted by marketers).

When do I stop wearing what I like and start wearing what I should?

When do I place my first order for power-walking shoes?  Or shoes with Velcro closures?