Fashion is not a bubonic plague and shouldn't be taken so seriously so don't be afraid to take risks! Sure, every risk taken may not work out exactly as planned but maybe it will. Bottom line, how will you know if you don't try?  

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However, when it comes to taking fashion risks, you must be willing to own the risks you take - confidence is key. Because confidence is so important when trying something new and or taking risks, if your fear or discomfort supersedes your urge to try it, then maybe don't do it. But if you have been yearning to try something that may be totally different from your typical style, especially if you continue to go back to it, try it! It's only fashion. Okay well maybe it's not ONLY FASHION since fashion is everything but point is you won't die if you try it and it doesn't work.

By the way, taking risks doesn't have to only mean trying something you have seen. Perhaps you've been envisioning a look; this is actually how a trend starts. Someone jumps out there and tries something that may not have been tried before and not only does it work for the person who tries it but others notice and then decide to do it as well.

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It's fashion and exploring fashion is meant to be fun, so go for it!