The Rules
Before you go to bed at night, ask your roommate, significant other, best friend — anyone who’s at your place, really — to select one piece from your closet. If you live alone (lucky you!), close your eyes and land your finger on a single item. This includes shoes, tees, scarves, belts, and tanks as well as sweaters, dresses, jumpsuits, and your more standout, go-to numbers.
Truth
If you don’t think you can construct a look around the garment in your hand, be honest about it. The “truth” aspect of this game is, in fact, most important. While you probably loved all of your clothes at the time they were purchased, there’s an inevitable point of retirement for most of them. Perhaps your style has evolved. Maybe your body has changed and you’re a different size (which is totally okay). Or, it’s quite possible you’ve outworn some of your items.
Dare
Now, if your roomie happens to pluck one of your all-time-favorite dresses from your armoire, then you will wear it tomorrow morning. Challenge yourself to style it with something new or unexpected. Invite heads to turn everywhere you go. Really, what’s the point of accepting a dare without taking a little risk?
The Win
In Linda Grant’s book The Thoughtful Dresser (this writer considers it a must-read), she writes: “Clothes as text, clothes as narration, clothes as a story. Clothes as the story of our lives. And if you were to gather together all the clothes you have ever owned in all your life, each baby shoe and winter coat and wedding dress, you would have your autobiography.” This is a pretty wise mentality about how your wardrobe weaves together so many life experiences. In a sense, that heap of clothes in the corner of your room is a sort of diary, and each piece falls into a different chapter.