Dear Ralph,

I’m getting ready to go to Greece next week. Is there any contemporary experience that so exemplifies the gap between how we want things to be and how they actually are better than commercial air travel?

To demonstrate, let me present your “Weekender Bag”:

Seen here, laid out in front of an antique luxury car, the tote version holding two wooden tennis rackets, next to a panama hat casually set on top of a seersucker jacket, the weekender bag is a travel essential only if you are traveling backward in time.

The reality is a little different. Imagine me with this bag over my shoulder, waiting in the long winding lines that are the inevitable reality of contemporary travel. I don’t want to set the bag down; it’s too nice to set on the filthy floor and I’ll just have to bend down and pick it up when the line moves three feet in a couple of minutes. So I wait, I shuffle forward; the strap is cutting into my shoulder, pulling me sideways.

I watch the people ahead of me casually inch their practical wheeled suitcases forward. I stand smugly in a sea of flip flops and sweatpants knowing that, despite the impracticality of the bag and the physical discomfort it is causing me, I am traveling in style.

Men are rarely presented with the choice between utility and style. Some men may have oppositional relationships to “dress shoes” or “suits”, but if these items are well made and well bought, they can be very comfortable and very practical. Women are presented with some form of this dilemma on a regular basis, the most obvious example being high heels.

Worse than the choice between style and utility that this bag represents, is the fact that it is self-imposed, a false choice that I have forced on myself as a result of looking at too many pictures of old movie stars disembarking planes and having read too many style-help-guides about how to travel in style.

This is a prolific genre of style writing. It ranges from ‘what to pack, how to pack, and what to pack it in’ to recommendations about which cashmere sweatpants to wear in the air. I’ve always been puzzled by this genre, mostly because I am not a business traveler nor are any of my immediate circle of friends, but also because the idea of getting dressed for commercial air travel is so obviously antithetical to the reality of the lounge outside the gate.

But worst of all, I’ve bought into it. I’ve probably spent as much time thinking about what to wear on the plane as I have thinking about what to wear when I visit the Temple of Poseidon at Sounion. So think of me, please, in an outfit colour toned to match my weekender. It doesn’t matter what bag we choose, we take our stupidity with us everywhere we go.

All the best,

S

PS – I’ll owe you a couple of extra letters when I get back in two weeks.