In my second installment of my Acquiring The Look series, I was inspired not only by the photo above, but by a couple recent business trips.  I spent significant time in some airports, and on planes, and while looking around I got to observe how people dress for a flight.  Now, as I was traveling for business I was wearing business attire.  But even those times that I travel for pleasure, there’s a certain image I wish to portray to those around me.  I will not wear sweatpants/track pants, flip-flops, or ratty t-shirts on a plane, ever.  I also wouldn’t wear shorts.  Jeans or chinos (or a suit if running right to an appointment) are good starters.  Wear a collared shirt, or a sweater (planes tend to get cold), shoes, or simple canvas sneakers, and some sort of jacket.

The image above looks like something I would wear on a plane.  It’s simple, and comfortable, and would take you from the plane to most destinations.  And remember, once you get there, you can change.  So don’t worry about jumping right from the plane into the pool.  You’ll have a few minutes in your room to put on your trunks and flip-flops.

Something like what you see above could be from a variety of places.  I managed to find what I think are good, affordable substitutions from J.Crew, Mr. Porter, Amazon, and Allen Edmonds as illustrated below:

 From top left

J.Crew Slim Secret Wash Shirt in Abott Tattersall $64.50

J.Crew Ludlow 2-Button Blazer $365

Drake’s Flower-Print Linen Pocket Square $85 at Mr Porter

Longines HydroConquest Stainless Steel Chronograph $1375 at

J.Crew Broken-In Chino in Urban Slim Fit $69.50

Allen Edmonds McGraw Penny Loafer in Bitter Chocolate Suede $335