The 10 Worst Stains, Ranked — and How to Get Them Out

From chocolate to red wine to paint to makeup, a lot of substances can become a headache once they come into contact with clothing. But how do they stack up against each other? 

With that question in mind, we rounded up 10 tough stains and took them to someone who knows all about them: Dr. Pete He, who holds a Ph.D. in chemical engineering and is the cofounder and chief scientist at Dirty Labs. We asked him to give each one a ranking, presented below with 10 being most likely to come out in a normal wash, down to 1 as giving your laundry detergent a run for its money. And don’t worry: We covered how to tackle them, too. 

A quick note: Of course, not all fabrics and clothing items are the same. With any stain removal tips below, make sure to follow your garments’ care label instructions for washing and spot test pretreatments before presoaking or pretreating.

If you’re dealing with an oil or grease stain, you’re in luck: Dr. He says animal and plant fats and oils used in cooking are not that difficult to remove because their chemical makeup is mostly triglycerides. In water, those types of molecules are emulsified by surfactants in laundry detergent relatively easily, and will typically come out in your normal wash cycle. Take a peek before throwing the splotched garment in the dryer, though — if the spot isn’t completely gone, the heat can set the stain. 

And if you’re dealing with a stubborn oil stain, Dr. He says you can take a few extra steps, first by pretreating the stain for 20 minutes with laundry detergent (or dish soap if detergent isn’t available), then machine washing in hot water with a warm rinse cycle.

“Cocoa butter is basically a plant-based oil — a fat. That is pretty easy to remove when compared to other things,” Dr. He says. “What makes chocolate hard is the cocoa powder.” 

Cocoa powder contains minerals such as calcium, copper, magnesium, and zinc, plus flavonoids and caffeine, Dr. He explains. Both flavonoids and caffeine are unstable at higher temperatures and can oxidize when exposed to air, meaning the longer you wait to treat, the harder this stain will be to remove. 

Your first step for this stain is to gently scrape off as much of the chocolate as possible. Dr. He suggests then taking laundry detergent, or dish soap in a pinch, and pretreating the stain for five to 10 minutes. Immediately wash with the same detergent in cold water.

Dr. He also notes that, when you’re dealing with chocolate, you should steer clear of using baking soda, vinegar, or lemon juice on the stain. Baking soda will react with cocoa powder’s aforementioned minerals and become insoluble, while vinegar and lemon juice’s acidity can make the flavonoids and caffeine even harder to remove. 

Nothing dampers a pasta dinner like looking down to see a red splotch on your outfit. Dr. He explains that this stain is a little trickier because tomatoes are rich in carotenoids, which are antioxidants that show off a variety of colors. 

This is another oxidizing stain — as in, the longer it sits, the more stubborn it gets. Dr. He recommends spot treating ASAP using laundry detergent, and reaching for dish soap, hand soap, or baking soda if detergent isn’t readily available. Immediately rinse under cold water and wash in cold or warm water using an enzymatic laundry detergent with pectinases listed as an ingredient. (It’s an enzyme made to remove plant-based stains.) If the stain has been sitting for a while, he suggests starting with a presoak in oxygen bleach and an enzymatic laundry detergent with pectinases for 20 minutes. Then, wash the item using both the bleach and detergent in cold or warm water. 

Coffee, Dr. He says, is somewhat similar to chocolate. “[Both coffee and chocolate] have caffeine for sure, but they also carry the color — those chromophores — in a brownish color,” he explains, adding that the chromophores (the part of a molecule responsible for color) and flavonoids make up most of the stain coloring in both substances.

With coffee in particular, however, Dr. He explains that there are more than 100 ingredients in a brew’s chemical makeup, including plant oils and waxes, carbohydrates, and proteins. It’s the coffee’s oxidizing components, such as caffeine, tannin, and other flavonoids, that will make you want to act on this one fast, especially if you like your coffee hot. Dr. He cautions that the high temperature can speed up the oxidizing process, making it even harder to get out the stain. 

To remove the remnants of your morning joe, try to treat it as soon as you notice the splotch. Dr. He’s suggestion is to spot treat with laundry detergent, subbing in hand soap, dish soap, or baking soda if detergent isn’t nearby. Rub the stain, rinse with cold water, and wash with an enzymatic laundry detergent in cold or warm water. For older coffee stains, pretreat or presoak the stain with oxygen bleach and an enzymatic laundry detergent for 20 minutes, then wash with that combo using cold or warm water. 

How stubborn can a makeup stain be? Dr. He says to remember cosmetics’ purpose. “When you develop those products, the number one principle is try to make them stick to your skin or lips,” he says. 

Makeup is made of a combination of oils, waxes, and coloring pigments, the latter of which can be composed of minerals or organic metallic compounds. “So think about that: If you have similar things on your clothes, those things can function as a permanent dye to the fiber,” Dr. He says. 

With this kind of stain, he says you’re going to want to start as soon as possible by scraping off excess makeup. Then, immediately pretreat with rubbing alcohol. “Rubbing alcohol is an organic solvent that can help dissolve oil-based pigments,” he says. Rinse with cold water, and then pretreat whatever’s left of the stain with laundry detergent and an oxygen booster. Finally, use the same detergent and booster in a machine wash with warm water. 

One thing Dr. He says you shouldn’t apply at any point? Your oil-based makeup remover. “That will stain your clothes,” he cautions. 

Dr. He notes that, in general, ink is made of a colored pigment and a solvent that will evaporate or oxidize to cure on a surface like paper — or sometimes, sadly, your clothes. Some ink is water soluble before it dries, he adds, but a dried ink stain will stick to a fabric’s fiber and can be pretty tough to remove. So, like most items on this list, ink is a stain best tended to immediately. 

Grab some rubbing alcohol to use as a pretreatment, rub it into the spot to help dissolve the pigment, and rinse with cold water. Repeat those steps two or three times, then pretreat again with heavy-duty laundry detergent. Throw the item in a warm or cold wash using that same detergent ASAP.  

If you don’t have those materials immediately on hand, you can look to the back of your fridge for sour milk (or mix fresh milk and vinegar). “Depending on the ink, soaking ink-stained cloth in sour milk right away can help remove the stain,” Dr. He says. “But, since ingredients in different inks vary significantly, this may not always work.” 

“Paint is an interesting one,” Dr. He says. “These days, in a residential situation, most of the paints are water-based, which makes [them] much easier to remove, especially before they cure.” But what makes them thornier, stain-wise, are the binders used in some oil- and acrylic-based paints. Those will put up a tough fight for rubbing alcohol and detergents. 

Because ink and paint are made of similar substances, Dr. He’s recommendations for removal are the same. You want to get to a paint splatter before it dries, if possible. Use rubbing alcohol as a pretreatment, rub the spot to dissolve the pigment, and rinse with cold water. Repeat two to three times, then pretreat and wash with a heavy-duty laundry detergent in warm or cold water immediately. 

“This solution should work well for latex and acrylic water-based paints,” he says. “For oil-based paints, this solution should help a lot before the paint is totally dried. But after it has dried, removing [an] oil-based paint stain from fabric materials can be very difficult.”

“Let’s talk about what is in the grape,” Dr. He says. Water and ethanol make up about 98 percent of the grape, while the remaining 2 percent includes tannins, pigments called anthocyanins, and chromophores that seal the staining deal, most of which are found in the skin. The tannins and anthocyanins are also some of the main players in making red wine an oxidizing stain, so it will bind to fabrics if not treated quickly.

But the acid in the wine plays a role, too, especially if the garment in question is made of natural fibers or certain synthetic fibers, like nylon. To give an idea of the effect this can have on your clothes, Dr. He says that, when cotton is dyed, it’s acid-washed before color is applied. “This acid wash opens the pores of the cotton to make it absorb the pigments better,” he says. “So the acid in the wine contacting our cotton-based clothes, it functions the same. It opens the pores of the cotton. When you have the pigments from the grape skin coming down to the fiber…it’s like dyeing your clothes.” 

If you find yourself on the receiving end of this spill, Dr. He recommends you first combine one part hydrogen peroxide and two parts water. If a washing machine is accessible, immediately apply the solution and an enzymatic laundry detergent to the stain, let it sit for three minutes, and machine wash using the same detergent with cold water. If you’re not around a washing machine at the time of the incident (or the garment isn’t machine washable), apply just the hydrogen peroxide solution to the stain as soon as possible, let it sit for three minutes, then rub and rinse the spill using cold water.

Whether you find one on a piece of clothing or your favorite set of sheets, a blood stain can be a bummer to deal with. Blood is yet another oxidizing stain, and an especially stubborn one — Dr. He says that its oxidative components will bond to the inner layers of fabric, adding another layer of difficulty (literally) to blood stain removal. 

“The red cell has enzymes that are pretty unique in that, in open air, when it’s exposed to oxygen, [the red cell] begins to get clogged,” he says. This is what causes the cells to penetrate fabric and bond to those inner layers. “At high temperatures, the clogging process is accelerated,” he adds. So when it comes to blood, cold water is your best friend. 

Dr. He recommends soaking a freshly bloodstained item in cold water the minute you see the mark. “Rub laundry detergent into whatever remains of the bloodstain. If detergent is not available, hand soap or dish soap can be used as alternatives,” he says. “Scrub the stain by hand in cold water by gently rubbing the sides of the fabric against one another. Rinse the fabric under cold water.” Throw the item in the machine or give it a good, thorough hand wash. 

If the stain’s dried, your pretreatment is going to look a little more complex. Dr. He suggests presoaking the item for 20 minutes in a mixture of cold water, oxygen bleach, and an enzymatic laundry detergent with proteases. He adds that, in a pinch, you can use your saliva, which contains proteases, to help break down a bloodstain. If the item is machine washable, throw it in a cold or warm wash and cold rinse cycle using that enzymatic detergent and oxygen bleach. For more delicate pieces, you’re going to want to hand wash by rubbing the sides of the fabric together or using a soft brush. 

“If you look at sweat from a laundry cleaning angle, there are two types,” Dr. He says. One is most body sweat, predominantly composed of water, salt, and a little body oil — all of which he says are not that hard to remove. The other is armpit sweat, which starts to have a different chemical makeup when we hit puberty. That’s where things get complicated. 

This sweat includes proteins, lipids, carbohydrates, and steroids, which then mix with sebum that brings triglycerides, wax esters, squalene, and free fatty acids. All of those biological materials then mingle with any underarm products you’re applying. Therefore, biological substances, bacteria growth, and antiperspirant and deodorant all can play a role in the development of pesky yellow or gray patches, according to Dr. He. 

Another tricky point with pit stains is that they can sometimes be invisible before they yellow, sneakily curing onto your clothing over time. The stains can start to smell beforehand, so take note if you’ve got a fine-looking item with a stink you can’t shake. 

The thing is, because this is yet another oxidizing stain (of course), your best bet is to get to it as soon as possible — potentially before you even notice it’s there. Dr. He recommends giving your sweaty clothes a wash ASAP so a stain doesn’t have a chance to oxidize and you limit bacteria growth over time. When you wash, make sure to use a detergent with a variety of enzymes that can target more components of the stain. 

If you come across a garment that’s aged and smells of sweat but hasn’t yet shown signs of yellow or gray, presoak the garment in that enzymatic detergent, or an enzymatic detergent and oxygen booster if your stain is really odorous. Follow that up with a wash in warm water. 

And if you are dealing with discoloration and want to attempt removal, follow a similar pretreatment. Pretreat or presoak the stain for 20 minutes with both the enzymatic detergent and oxygen bleach, then wash with the same combo in warm water. 

Apartment Therapy’s Laundry, Sorted vertical was written and edited independently by the Apartment Therapy editorial team and generously underwritten by Samsung.