Warning: I'm about to drop an opinion on a particular fashion style that you might feel partial to. Like Squashgate, please know I'm mostly writing about this in order to fill up space and will easily back down from my opinions when confronted. Fortunately Gawker has my back on this issue (I spotted this ad yesterday morning so I promise I'm not just re-hashing their rant).
For reasons unknown to me I have a subscription to Town and Country magazine (even though I can't afford anything in it I like looking at it and pretending I'm the type of person who can drop $20K on a pair of earrings I'd wear two or three times a year). T&C puts out a wedding issue and even though I'm all settled I still like looking at the issue ($40K for a pair of earrings you'll wear once in your life). Strangely, it wasn't the jewelry, or the $1200 wedding cake that caught my eye for all the wrong reasons in the latest issue, it was this photo in an ad for a company that makes bridesmaids dresses:
I feel like this photo is the Kinsey scale of your preppiness. How much of these guys' outfits do you hate? If you think they're totally cute and normal, then you're a 100% old school prep who doesn't bat an eye when people use the word "summer" as a verb. If you can abide the jacket and pants but not the shirts, you might be half prep. Me, I gauge I'm about 75% prep based on the fact that I think these outfits are totally normal and nice for a coastey-type wedding but then when I get to the flip-flops I am filled with rage.
Preppy style was not the thing when I went to high school in the midwest, but then I got a huge dose of it when I went to college with a bunch of eastern (and southern) folk. I developed a distaste for male dress-flip-flops from being around guys at college who wore them (so I feel the same way about Nantucket Red). I knew some very nice guys who dressed like this but unfortunately I also knew some guys who embodied the preppy prick so thanks to the bad apples, now to me the fancy-guy-flops is a prick look that screams of entitlement or striving to appear entitled. Only a certain kind of guy can get away with this look, the kind of guy who can afford to purposefully make himself look worse. These guys probably own many pairs of nice shoes but they're rich and are going to inflict their bare feet on everyone because they can.
I'd normally worry that my extreme reaction to flip-flops with dress clothing is a sign that I'm an antisocial human being, but this photograph happens sums up perfectly what is wrong with male dress sandals: look at what the girls are wearing! The kind of flip-flops that make me angry are the ones that are worn at occasions where the ladies are expected to wear heels. Ha ha, let us all enjoy how rich we are and rich we look and how comfortable we are while the girls have to pretend like they're not dying inside. Let's all have a cigar. Hey girls, mind bringing us a drink? You have to walk all the way down the gravel path to the bartender to get them, but that's life. If you get cold maybe we'll lend you our blazers.
So, if my argument that "dress flops=jerk look" doesn't fly, let's at least apply the code of chivalry to this style. If the girls are in strappy heels and strapless dresses, the very least the guys can do is throw on some shoes--otherwise, they're rubbing their comfort in the gals' faces, unless that's what it's all about of course.