"Soy sauce?" "And berries?" "Chocolate syrup?" asks a white-haired, chubby, grandmotherly woman at the beginning of what I think is the most annoying commercial currently on television, for Lee Performance Khaki pants. (See it here.) The woman is in the kitchen of two people, presumably her son and daughter-in-law, and she is reeling off types of stains that may be inflicted on innocent trousers. At the spot's climax, the svelte daughter-in-law boldly spills a glass of red wine onto her slacks; then, calmly, she wipes the stain off—and magically removes all traces of it.

"No f-ing way!" I screamed at the tube when I saw this. I am a notorious spiller, a ruiner of garments par excellence. And my worst stain of all time happens to have been inflicted by red wine: Seven years ago, about an hour before my guests—fellow food writers—were to arrive for my first formal dinner party ever, I realized that I did not own a proper tablecloth. I called my then-boss, and she offered to lend me one from her own stock. I ran to her house, retrieved a gorgeous Provençal-patterned number, and put it down on the table with 15 minutes to spare. Three hours and many bottles of pinot noir into the dinner, one guest spilled wine all over the cloth. Suffice it to say that it took a two-liter bottle of club soda and a very high dry-cleaning bill to fix the problem, though a trace of it remained. I was forgiven (and, yes, I bought her a new tablecloth) but am eternally ashamed.

So the new Lee Performance Khakis, made of a new fabric called Nano-Care, struck a particularly sensitive chord. I simply had to check out the pants, and pronto. I was not interested in the art of stain removal: All those old wives' tales about pouring salt on the wound and other such alleged remedies are useful only after you're screwed. What I wanted to determine was something more general and more important: whether or not there is any good way—either by buying some special fabric like these pants or by pre-treating your other fabrics—to prevent stains before they can damage your reputation.

The Science
Three stain-preventing options quickly emerged as potential winners:

Nano-Care: Nano-Care is a synthetic fabric made by a company called Nano-Tex, which was founded in 1998 by Dr. David Soane, Ph.D., for the stated—if difficult to interpret—purpose of "controlling the design at a molecular scale, making possible the creation of limitless materials." According to the company, here's how the fabric works: "Molecular structures are attached to cotton fibers creating an invisible barrier that causes moisture and stains to bead on top of the fabric and prevent absorption." This means that the fabric is built of fibers chemically treated (at their molecular level) such that a liquid is unable to be absorbed into them and form a stain, while a semi-solid item, like ketchup, say, can be wiped off. In this day and age of worshipping everything organic, a product like Nano-Care is positively rebellious.

Scotchgard: Though Nano-Care is in a class by itself at the moment in terms of its stain-resistant aims, there are other ways to keep your clothes clean. The time-honored, Happy Homemaker method is, of course, Scotchgard. This "extremely flammable" spray contains enviro-unfriendly baddies such as hydrocarbons and propanol. It is an aerosol spray that is supposed to protect all sorts of fabrics, including silk and linen, if you apply it to clothing and then let it dry. It does on a macro level what Nano-Care does on a micro level: Spraying clothing with the chemicals applies a coating to them that makes it hard for stains to absorb into the material. This is also not an organic procedure, but perhaps it's better than investing in a new wardrobe.

20 Mule Team Borax: Another preventative staining measure exists: laundry boosters. These look like laundry detergents but are more intense and have other household uses—imagine a detergent that could also be a tub-and-tile cleanser. One brand, 20 Mule Team Borax, looked—OK, and sounded (love the name)—intriguing. In a detergent-type box, 20 Mule Team Borax billed itself as a "multi-purpose household cleaner" that can be used to pre-treat clothing. When added to your wash, it does several things that help it clean. It changes the pH of the solution swirling around in your washer to make it more alkaline (this makes detergents more effective), it creates hydrogen peroxide (a bleaching agent), and it acts as a chemical buffer in the reactions that get clothes clean. The enzymes in Borax also coat the fabric and thus help repel stains before they get a chance to sink into your clothes. Though you shouldn't rub this stuff in your eyes, it is made of a naturally occurring mineral—borax—and contains neither phosphates nor chlorine. (To find out more about the chemistry of borax, click here.)

The Test The first thing I did was order up a pair of Lee Performance Khakis, which were surprisingly hard to find in the New York City area though they are readily available at J.C. Penney stores throughout the country (I ordered mine from Spiegel.com).

Then I dug up a pair of old, worn, 100-percent-cotton khaki pants from my own collection. I also found a pair of my husband's old 100-percent-cotton khaki pants, ruined because he'd torn a big hole in an inconvenient location.

For the first pair, I followed the Scotchgard instructions by spraying the fabric evenly, holding the can upright about six inches from the pants. The container recommended letting one coating dry and then applying a second layer, which I did. ("Two light coatings, drying in between, are better than one heavy coating," it instructs.) The recommended drying time was 24 hours, which I also followed. The spray affects the texture of the pants in such a way that they become sort of grainy—almost like they'd been sprayed with heavy starch. And the fumes emitted from the Scotchgard are not for the faint of heart, literally. Scary label warnings include: "Danger! Extremely flammable. Vapor/mist may be harmful. Intentional misuse by deliberately concentrating and inhaling contents can be harmful or fatal."