If you try to pare down your wardrobe, you'll end up with items you want to keep, items you want to toss and items that are somewhere in between. Before you decide on those "maybe clothes", give them a wear.
Photo by Steven Depolo.
Sometimes clothes become "maybes" because you bought them on a whim, or somebody else gave them to you. But sometimes an item becomes a "maybe" because you haven't really given it a chance. That's why Marlen Komar at Apartment Therapy suggests you try and wear the clothes that go into your maybe pile at least once — maybe even a few times. Perhaps you pull it off better than you thought and you actually do feel confident wearing it. Or maybe after trying a couple different outfits you can find a way to wear it that you haven't thought of before. If you still feel unsure about the item after giving it an honest chance, donate it.
No Regrets: How To Clean Out Your Closet & Feel Good About It Later [Apartment Therapy]