For the past four or five years, I haven’t bought a pair of jeans. Instead, I’ve shopped in my younger brother’s closet. Unable to resist buying new pairs, my brother David has happily passed along his ‘hand-me-ups’ as they’ve been displaced by newer editions.

The problem: my brother’s waist is about an inch and half larger than mine. And while I’ve taken to simply cinching down the excess with belts, a slew of female friends have recently pointed out that, in short, it looks retarded.

So, I set out to buy a pair or two of new jeans. And, in the process, I discovered I’m no longer really a 30-30, and closer to a 29-30 instead.

After extensive searching, I made a second discovery: while 30-30 jeans are easy to find, 29-30’s don’t seem to exist. Drop to a 29 inch waist and everything comes solely in 32 inch length. So, realizing I’d already spent embarrassingly long on the jean search, I quit while I was ahead and picked up two 29-32 boot cut pairs from Banana Republic.

Which sent me, after washing each pair twice to counter initial shrinkage, off to have the jeans tailored.

Previously, I’d simply taken any about-right length as good enough. Now, faced with the chance to trim to perfect size, I could angst about a whole brave new world of jean fitting concerns.

Shorten them to fit with a pair of oxfords, and a set of flat-bottomed sneakers drags the back of the jeans an inch and a half underfoot with each step. Flip things around to fit the sneakers, and the jeans look like high-waters with anything else.

So, after a week or two of serious consideration, I simply gave up, had them tailored at some arbitrary length mid-way between the sneaker and soled-shoe ideal, and set about re-convincing myself that the whole thing isn’t even vaguely important in the broader scheme of my life

For borderline obsessives, too much choice is a dangerous thing.