I'm such a sucker for oversized button downs. They never fail to look simultaneously chic, sophisticated, relaxed, timeless, comfy, put-together... the list goes on. While the classic button down has been around for decades, it's really Coco Chanel who first popularized the style for women around a century ago, with lots of borrowed-from-the-boys shirting and tailoring details. And, of course, there's that famous scene from Risky Business involving oversized button downs, worn by everyone. All of which is to say, it's an iconic piece that has been around, is currently around, and will stay around.
One of the reasons they're such a genderless, season-less staple is the sheer versatility factor. You can wear an oversized button down to the office on Friday, and then as a swimsuit coverup to the beach on Saturday. Keep it classic with jeans and sneakers, or slip into some heels to style yours as a dress. You can even wear one around the house as loungewear and then tuck it into a chic slip skirt to go out at night. When I say the options are endless, I mean you can get at least 50 outfits out of just one generously-proportioned button down. (No, really!) And to help track down the very best oversized button down shirt for you, we've rounded up 14 of our faves, ahead.