Figuring out what to keep in your closet really comes down to learning what clothes and accessories make you feel the most you. Take Jane Birkin, whose style I have always loved. She doesn’t exclusively wear jeans, tops, casual shoes (sneakers, ballet flats) and her Birkin bag (or when she was younger straw basket), but the most iconic pictures of her usually capture her in some form of those items. Being an actress she can basically wear whatever she wants–no work uniform, but still those clothes speak to her personality. They are her signature.
The first step to deciding what to keep and what to let go of in your wardrobe is figuring out what you want your signature style to be. Sometimes it seems easier said than done. Even when you have a pretty good idea on what makes you feel your best, many of us (myself included) go off track and end up with pieces that don’t feel right. Maybe you were having a romantic ruffle moment when you’re more of a minimalist, or the reverse–you bought an en-pointe oversize blazer when you feel much better in a dress.
How to begin determining your signature style? Start noticing what you have to wear that makes you feel really good (it has to be something you can wear most days, not some fantastical evening gown). Those items you wear that make you feel unlike you? You know in your gut what they are and in fact, I can think of two dresses I still have that fit into that category. Move them out of your closet for two weeks and see if you miss them. I’m going to guess that you won’t even notice they’re gone. Then think about letting them go. It’s one step in the process of sharpening your style.