Recently, I cut the sides of my hair around chin length. I also dont pull my hair back tightly, keeping it messy but still protected. Tbh im more confident with my hair loose but I freak out when I'm outside in the cold, windy weather. My need for long hair with minimal split ends is higher then my need to feel confident. Having bangs, side bangs, face framing layers, etc, can really make a updo look cuter!!
I think the most important thing is that you feel happy with your hair. Feeling confident is also important. But I really get where you're coming from! I hope you will feel better about your hair on the future.
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