Keeping the bottom button undone on a vest is the sort of information that fathers used to pass along to their sons, along with how to flush a public toilet with one’s foot rather than one’s hand. But as I am older than most readers of this website, allow me to offer a bit of fatherly advice about vests and buttons.
In leaving the bottom of the vest unbuttoned, a bit more trouser is revealed. That was fine in 1930 when vests were cut properly and many men wore braces. Today, however, two things are obvious about modern vests. One is that they tend to be cut too short, particularly if they are part of a suit. Secondly, some people – stylists at least – seem to think that a little peek-a-boo with the belt buckle is an attractive sight.
It is not. It makes one appear to be wearing a very cheap and ill-fitting article of clothing (this reminds me of the classic definition of the English bespoke suit: a beautiful and expensive garment that appears to have been made by hand for someone other than the current wearer).
There are several ways to deal with the problem of short vests that reveal the detested shiny belt buckle. The first is, as in antiquity, to wear braces, which will minimize the problem but requires one to practically disrobe if one needs to drop trou during the day. Another way, if one is purchasing an odd vest rather than one that is part of a suit, is to size up, so to speak. I am a 42 regular, but when I buy separate vests, most usually from tack shops, I choose 42 longs. The extra inch or so of vest length solves the problem. But with off-the-rack suits that include a vest, this is not usually an available gambit unless you can do some surreptitious switching of pieces from hanger to hanger.
So here is a simple little trick to deal with the buckle issue, and as far as I know it has nothing to do with the Ivy League specifically or higher education generally. In fact, it is a 1950s greaser technique, a concomitant style to the pointy Flagg Brothers shoes of the period and the habit of taking two rolls up on the sleeves of your short-sleeved shirts. The instructions that follow are for right handed men; lefties should reverse the instructions. As you stand with your trousers on and your belt in hand, you would normally insert the non-buckle end of the belt strap under the first belt loop to the left of the fly, as you look down. But, instead, ignore the first loop and insert the belt under the second loop and then all the rest.
When you are finished threading the strap completely around your waist, the buckle will be between the first and second belt loops, at your side, rather than centered in front. Only the belt strap will appear at the front, and even a relatively short vest should cover it, even if the bottom button of the vest is left undone. The strap, though it may inadvertently peek out from time to time, will be dark enough against the trouser fabric to not be noticeable. If you will follow old Dad’s instructions, you will look like an adult and not appear to have a shiny Cyclops peering out from the top of your pants between the points of your vest every time that you raise your arm or take a deep breath. — CHUCK WATKINS