Keeping one's clothes classic and simple is always a good idea with more formal modes of dress, but it's frequently an even better idea in the casual realm. There are a lot of inherently American combinations which have stood the test of time, but I think my favorite is this:White oxford and blue jeans. Can't be beat. Finished off with boat shoes and a surcingle belt. What better outfit is there for the first really nice day of Spring, spent largely outdoors with the wife and kids.
To me, the key to an outfit like this is the shirt. These days it seems to be all the rage to prattle on about these jeans or those, and which are more "authentic". As far as I'm concerned, jeans are from Levi's, and you wash them when they get dirty. No, the shirts the real thing here.
This kind of thing works best with a really old shirt in heavy oxford cloth. It should be one that used to serve as a dress shirt, but its been washed and worn so many times that it has reached an absurd level of comfort. Worn un-ironed of course, it's heavily frayed collar is unbuttoned:the sleeves rolled in an effort to mask the hole worn through one elbow:And yet its still bright white. I think Ralph Lauren made a lot of money selling this very concept in pre-packaged form to the young-uns, which is all well and good, I suppose. But a hole in your clothes only counts if it's your hole.
Keep it simple: wear a white shirt to death, and then keep wearing it. Just make sure your wife doesn't throw it out when you're not looking.
p.s. since when do Baracuta jackets cost $265? When I was a kid, we all got them for school jackets because they would go on sale at Sears for $10. I also remember them being popular with old men on Social Security. What gives?