The Essential

True story:* Guy's got a Big Day at Work. Guy breaks out his five-year-old Big Day at Work suit. Guy wears it to the office, mighty impressed with himself, until Guy's pants split clear up the back, right in front of his boss and other assembled dignitaries. Guy spends the rest of the day in borrowed pants, no longer mighty impressed with himself. The lesson here: Don't wait until it's too late to realize you need a new suit. Instead, once a year, right about now — May offering optimal suit-wearing weather — take stock of your suits; remove the weakest, shiniest, most worn-out link; and upgrade with the best suit you can afford. On the higher end, we like the quality and variety in Giorgio Armani's made-to-measure program: You choose the cloth, cut, and details from an Armani-approved menu of options, and Armani's tailors take more than a dozen measurements to make sure the jacket and trousers fit your body just about perfectly. It ain't cheap, but for a good-looking suit that won't quit (or split) on you for a good long time, think of it as a bargain.

*Guy may or may not be a senior editor at this magazine. Guy is pleading the Fifth.

Cashmere made-to-measure suit (from $2,995), cotton shirt ($345), silk tie ($195), and leather shoes ($625) by Giorgio Armani.