In case you missed it, that moment was your wake-up call. Your go-to pair of jeans might hit slightly lower than Lauer's rib-cage-rubbing pairs, and they might have a slightly more cosmopolitan wash—darker, with maybe a strategic patina of wear—but if you picked them out all by yourself a couple of years ago and have established a monogamous relationship with them, there's a high probability that the two of you don't look so cute together anymore. There's also a very good chance that quite a few people—casual observers, the guys at the office, and all your wife's friends—think this and aren't telling you.

"Guys are a little afraid of jeans," says Rogan Gregory, founder of the instant-hit denim label Rogan. "They don't want to deviate from their tried-and-true five-pocket pair. But you can't wear those with a sports jacket. It's not a tight look. You can't just stick with your 'safe' jeans."

No one's suggesting you embrace calf-clinging skinny jeans, or ones that are torn up, or the conspicuously overdistressed kind twentyish guys wear on Cherry Bomb binges in the big city. That would be a mistake only slightly less tragic than Mr. Today's suburban-mom jeans. But it's worth taking a good, hard look at yourself in the mirror from the waist down.

"You have to reevaluate and give it some thought," says Carl Chiara, the design director of Levi's Capital E and Levi's Vintage Clothing. "Some guys don't even try their jeans on before they buy them." At the moment, Chiara is meticulously replicating a pair of Levi's from 1890—a simpler time, back before words like rise and wash and whiskering embedded themselves in your personal vernacular.

If you're feeling paralyzed by choice, it's understandable. But to take a grandpa-in-the-La-Z-Boy, self-righteous approach and stick with your L.L.Bean—cut pair is to do yourself a disservice.

"I don't think it's that big of a commitment to go shopping once or twice a year," Gregory says. He adds this incentive for double-checking that your jeans aren't the sartorial equivalent of a minivan: "I think women do notice. I've been told on many occasions by guys—Your jeans got me laid.'"