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Yet much of the time choosing what to wear feels intimidating, uncomfortable, and awkward: we don't know what to wear or how to wear it, and we definitely worry whether what we're choosing is right for us. That's funny, if you think about it: in most aspects of our lives we have a really good sense of what we want and what suits us best.
But with clothing, somehow it's different. Where we get lost is when we think dressing well is more complicated than it really is. We think that looking good is an unattainable thing that only cool, skinny, tall people -- models essentially -- can really pull off...and the rest of us are left thinking, "Oh well." But that's not true -- at all. We just go to the store and choose. It's not such a big decision.
Think of the clothes you see at fashion shows as art.
What you see at fashion shows is designed to make an artistic statement. For the most part the clothes you wear should be used as a tool to increase your happiness and confidence and sense of well-being. Start by separating those two ideas: there's art, and there's your daily "uniform," the day-in, day-out clothes you wear that can sometimes be an expression of art if that is in your personality... but sometimes just is what it is: your daily uniform.
That's step one. Separate art from everyday, and separate trying (and probably failing) to make an artistic statement from wearing clothes that make you feel empowered and at your best.
Remember a time when you wore something and felt great.
Maybe it was in college, maybe it was years ago, maybe it was last week... but at some point you felt great in something you wore.
" I'm reasonably fit, so I like how that looks, but I'm also shy, so I like that it's understated."
Never wear something just because other people are wearing it. Never wear something just because you think you should. Feeling hip will never outweigh feeling comfortable and confident -- in fact, if hip is not right for you, you'll actually feel insecure and self-conscious. Your clothes should always empower you.
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