Anyone who has worn an ill-fitting bra or the wrong bra size knows that doing so can ruin an otherwise flawless outfit—or worse, an entire day. (The breast pain and backaches that can come with large breasts are nothing to joke about.) The solution is finding and investing in a set of undergarments that are the right cut, fit, and size—but it’s not a simple solution.
Lena Dunham told us that she loves “a slightly baggy, but fun underpant,” and called out these Joe Boxer string bikinis as ones that fit the bill. “Joe Boxer was cool and hip when I was 12, and now it’s a Kmart property. Leaving aside the ethical implications of that, I fucking love the underwear,” Dunham says. She told us she orders the bikinis in a large to get her preferred loose fit. “A medium might be more supportive of my butt, but this gives me a little tail,” she says. “A six-pack of three solids and three patterns for me is the perfect balance.”
Here are a few telltale signs that you may not be wearing the right bra size: wrinkling in the cups, underwire poking the sides of your breasts, a band that rides up, cup spillage, slipping straps, or a bra that hikes up when you lift your arms, says Sandi Simon, a fit consultant at Bra Smyth, in New York City. (Keep in mind that certain factors can cause you to change bra size, a weight gain or loss, a new exercise regimen, pregnancy, and a change of diet, among them.) If you suffer from any of the fit issues above, head to a professional bra fitter—or bust out the measuring tape and follow the steps here.

You should not be able to stick a finger under the center gore. It should lie flat against your chest.Which brand is best for you? Bra sizing DOES vary by brand. The descriptions below may help you select the right brands for you. A smaller-busted woman may need to go down a size to fit well in a brand designed mainly for larger women. A large-busted woman may need to go up a size to fit well in a brand designed mainly for smaller-busted women.
When we talked to model, actress, and entrepreneur Amber Rose about the things she can’t live without, she told us a story about going underwear shopping: “So my friend Chyna, we were at Neiman’s the other day, and I was picking out some La Perla underwear,” said Rose. “They were like $120, and Chyna is like, ‘What the hell are you doing? Why are you buying such expensive underwear?’ And I was like, ‘Girl this is going to change your life,’ so I bought her a pair.” If you’re on the fence about splurging on pair of underwear, Rose makes a compelling case for doing so. “I know this sounds crazy, but wearing expensive underwear under your clothes gives you a certain type of confidence in a really cool way.”
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