Recently, my friend Dana asked for some help with her spring wardrobe. She told me that she had a few pieces that she wasn’t sure how to wear and that she had a few things she needed to buy. I didn't go into the day thinking we'd have too much to do. We started by having a lovely lunch, and then paged through the Lucky Guide to Mastering Any Style. I wanted to get an idea of styles she really loved so that we could judge pieces she already owned by that standard. Dana was very “meh” about all the styles in the book, to the point that I was getting a little worried, until we got to “mod”. “I like THAT, and I like that, and I like that…” Ok, done. If you know Dana, you know that she has a good boho vibe going on already, but I would have never guessed that she was so into 60’s and mod looks.
We headed into the bedroom. Dana has a small closet, your typical 80-year-old-house-sized closet, but I'm telling you, it was like one of those clown cars. I couldn't believe how much she actually had packed in there once it started coming out. "I never know what to do with this, this I wear with this one other thing, this I need something with this exact shade of green to go with, this was a gift..." And so on. For a long time. I was getting overwhelmed. Just when she would tell me, "ok, I think that's it", I'd ask, "What about those storage bins on the top shelf?", and she'd remember that, oh yeah, those were also full of sweaters she didn't wear. Finally, I said, "Dana, the problem is not that you can't make these things work. No one could make them work. Plus, you don't even like them that much to begin with!" The low-key-only-need-help-with-a-few-options session was clearly going to be more than that.
Dana has had an interesting style evolution. At some point, she had decided that she wanted to upgrade her self-described "t-shirt and jeans" style, so she started trying to add pieces with more interest into her closet. By the time I saw her wardrobe, almost everything had "interest", and therefore nothing worked with anything else. She's also on a tight budget, so she felt bound to all these pieces because they "might work" and she'd have them "just in case" she needed an option without spending money.
After her bed was covered in clothing, we started with the obvious decisions. Things that didn't fit, things that were a gift, things that were worn out all went in the donate pile. I pulled everything to one side that she really loved, that she was excited about when she talked about them to me. This was maybe ten or twelve pieces.
Then we started the long process of evaluating all the "maybe" pieces. It's hard to let go of something that you've held onto with the hope of making it work. It's hard to accept that, actually, it's not going to work. Out went the mud colored pants, out went the awkward-length skirts, out went the tops that only worked with one specific cardigan over them.
Happily, there were also many pieces that did work. Dana just needed an outside pair of eyes to tell her that it was ok to wear x shirt with x pants, and that x dress didn't have to be relegated to dressy events, but could actually be worn to work as well.
I wasn't kidding when I said long process. We worked on Dana's closet for 5 hours. By the end of our session, she had gotten rid of three or four large storage bins of clothes, but more importantly, she had a new perspective on her closet. She realized that hanging on to all of these one-hit-wonder pieces in her closet was actually making getting dressed harder, not easier. She was able to accept that sometimes things just don't work and that you shouldn't beat yourself up about trying to make them work. She realized that, actually, you can have most things in your closet work with most other things, and if that's the case, getting dressed in the morning becomes much easier.