Lately I've been toying around with the old preppy two collar look. Though admittedly something of an affectation, dare I say tres Muffy Aldrich, I find it comes into it's own late Spring/early Summer. I find it handy on warmish days of variable temperature, where the outer shirt can act as more of a light jacket over the tennis shirt. I generally stick to solid, light colored tennis shirts under soft old dress shirts. In this case, a well worn pink tennis shirt from Lands' End (bought new four Summers ago, see here) and an old Brooks Brothers oxford with an unlined collar (thrift shop, $5.49). Remember, this is about dressing comfortably, not like a slob. There is a difference.
I know this may cause a bit of wailing and gnashing of teeth among the hard-liners, but I think it works best with the top shirt untucked, jeans, and a ball cap. Like I said, this way the top shirt is more of a light jacket. Shorts or khakis work as well. (I hope nobody out there is zooming in on this picture and keeping a detailed journal of the books on my shelf, what time the clock reads, and the presumed provenance of my furniture ...snark,snark,snark. Sorry).
It can work dressed up a little too. Here, a white tennis shirt and university striped oxford are worn tucked into khakis with a navy blazer and surcingle belt for a parade on Memorial Day weekend. The flag was given to me by an old lady in the VFW women's auxiliary.
In either case, bare ankles and moccasins are de rigeur. Camp mocs with the jeans, penny loafers with the blazer. Of course boat shoes work as well.
I must admit to having some trepidation not long ago about my, or anyone's, ability to pull off the two shirt thing. It always seemed to smack of some mean spirited spoiled character from some bad movie from the 80s. But I've grown to enjoy it, and I've found that the trick to wearing it is, as with so many other sartorial "moves", confidence. It's kind of like jumping in cold water at the beach: once you just go in and dunk, it gets easier. It helps not to have to much concern what others think of you.
Of course, to be fair, I do live in a liberal place full of arty college kids of every stripe, so most likely I'm just perceived as a Dad whose becoming more and more of a fuddy duddy the older he gets.
p.s. lots of great new Summer stuff in the Shop.