For many people, and understandably so, the second that vacation begins, the care to construct a styley look ends. And truly, I will never fault anyone for taking off the work clothes and slipping on the t-shirt, shorts and flips-flops.

On the other hand, as long as you gotta wear something (assuming you’re vacationing with family in, say, San Diego, and not at “Sea Mountain Nude Hotsprings”) why not wear something well put together?

The trick is this: if you know that you won’t have the headspace to pick out a bunch of vacation outfits as you rush to cram your suitcases, pick them out in advance. Way in advance. In other words, identify a couple of pairs of pants, a few shirts, a pair of shoes, and yes, a classy layer-piece: a sweater or an unconstrcuted blazer or both.

Then, when your plane takes off in three hours and you still haven’t filled your suitcase, you need not panic: you know what you’re packing.

As Gabi and I approach our first week as (and with) future-family, I’m struck by two competing forces at work. First, there is, well, the familiar. Gabi’s family is very tightly knit and meals with them are full of laughter, good-natured ribbing, and decades’ worth of stories. They seem to appreciate and understand my humor, although folks are divided on whether my puns are brilliant or groan-worthy.

On the other hand, there is the unfamiliar. Deeply unfamiliar. People who are dear to me, and have been for years, take on roles of new significance. Future father-in-law. Future mother-in-law. Future brother-in-law. I have never really known these roles in my life, and I’m acutely aware of this, the way a new article of clothing feels very there.

It seems appropriate, in these circumstances, to wear something fitting this odd and beautiful confluence of well-known and never known. Here, on this San Diego beach, what could do that better than comfy sneakers, a soft sweater, my old hat – and a red flower in my lapel?

#fashion #mensfashion #vacation #mensstyle #mensstyle #Turning41