I used to have an on-going source of misery in trying to figure out what to wear. I was 100% unhappy with my clothes 100% of the time. I went clothes shopping and tried on clothes and hated whatever I put on. I bought something so I'd have something to wear. I hated all of it. I felt like a loser. I felt ugly. I felt stupid. It all made me feel as if my body was defective because I thought I looked so strange in my clothes.
A few years ago I started tracking my spending. I read that by tracking it as if you were the bookkeeper for someone else's business, you will become aware of when you're spending money that doesn't benefit you and when your spending does benefit you. At the end of the year I added it all up and discovered I had spent a tremendous amount of money on clothes and didn't have a thing in my closet that I actually liked. What I really wanted was the ability to travel, and I could have taken several lovely trips on the money I spent to buy clothes I didn't like.
So...I started buying used clothes and very cheap clothes since I didn't seem to be able to buy stuff I looked good in and actually liked. What the hell - spend as little as possible. To my surprise I found a bunch of clothes that I really liked and that I looked good in that were used.
Eventually one of my friends told me about a store that sold clothes for middle-aged and older women that were beautiful, fashionable, that fit our body types, and that seemed to be indestructible - never wrinkling or wearing out. Those clothes were exactly what I had been hoping to find my whole life. Flowing, beautiful colors, very basic blacks, etc.
So...for the past 20 years or so, I buy 90% of my clothes at that store. I don't need to put much thought into what to put on every day because what's hanging in my closet is simple and already matched up. I could simplify a little more, but that would take a little bit of the fun out of dressing myself.
Being able to stop worrying about what to wear, how I look and whether I'm dressed appropriately has opened up space in my mind and my time for other much more valuable things.
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