Made from Supima cotton, the Los Angeles-based brand designed its updated signature staple to feel broken in from the first time you wear it. It has a looser boxier fit, which helps the shirt drape perfectly and makes it easy to style. I got it in black, but it’s also available in navy and white, along with limited-edition brick red and varsity blue. The shirt was so flattering and comfortable that I wore it for three days straight. I tucked it into jeans and wore it with a cardigan for a casual look, but the crew-neck style would work just as well with skirts, trousers, or a blazer if I wanted to wear it out to dinner or at the office. I could also see styling it underneath dresses when the weather gets warmer. I even slept in it for a night, and after I washed it in the washing machine—in cold water and dried on low—it didn’t get stretched out or wrinkled, or lose its soft feel. To buy: $40; american-giant.com. And if a boxy fit isn’t your go-to style of T-shirt, you’re in luck, because American Giant uses the same Supima cotton for its classic V-necks, tanks, and regular crew neck styles. At $40 a piece, it might seem a bit steep for a basic T-shirt, but seeing as you can wear it with practically anything and it holds up after washing, I’d say it’s well worth the price. Plus, you can save $20 when you buy three. Shop the Classic Relaxed Fit Crew T-Shirt here and browse other styles below. To buy: $40; american-giant.com. To buy: $40; american-giant.com. To buy: $40; american-giant.com.