It's Andy Fish!

I’ve always liked your style and I was wondering do you think it’s OK for a man to wear a baseball cap– and I’m not sure what your feeling is on sneakers after 45– I’d really like your opinion.

I’m on the record saying you should not wear a baseball cap after the age of 11 unless you’re playing on a team–it’s a child’s item, why not just buy a beanie with a propellor on it?

But I do own a baseball cap, it’s for Boston College, I bought it in a spur of the moment because it’s a neat looking cap, the brim is properly bent (I hate flat brims) and the color is cream with blue writing on it.

I’ve worn it officially once and my Number Three Son, who himself often wears a baseball cap took one look at told me I should be flagging him in to run for home.

So I won’t wear it again. I do own a Fedora which I wear when it’s raining or snowing. I always get positive comments on it.

As for sneakers, I do think everyone should own a pair, the simpler and plainer the better. Even past 45 we old guys do occasionally do athletic things and I’m not going to ride my Ten Speed bike or play Pickleball wearing my Italian Loafers.

But as an everyday shoe? Nope. Get some comfortable leather shoes. If you spend the money they’re actually more comfortable than sneakers and you look like a grown man.

And by the way, NEVER EVER EVER those sneakers with the super wide base (New Balance?) because you look like you are heading out to the short bus.