Dressing well takes practice and you have to take some risks. You may have to get it wrong a few times before you realizes what works for you but that's absolutely normal. The social risk of wearing something outside your comfort zone can be intimidating. You feel like everyone is noticing your clothes or shoes or hair, but you are uncertain of what they think. You just don't feel 'at home' in your own clothes. I am very sure Mr Kanye West must have felt kind of awkward when he stepped out in his white stripped 'shadeless' shades which by the way became a trend at the time or his sneakers on his tuxedo suit but no one will argue with me how huge Kanye is as a fashion icon or will ever doubt his sense of style. Rihanna as well is known for her immense sense of style but often steps out in bizarre outfits and am sure she also would have felt awkward at first but they thrive in confidence in pulling off the risk taken. You just need to overcome the initial awkwardness until it passes. Until then, you can't judge the way they look on you objectively.
Remember ' The fit' is everything but there are always rules when it comes to fashion. They can be broken but you have to know them before you can break them.
If you see a style that you really want to try but are a little intimidated by it, practice wearing it around your house till you gain confidence with it. You need to feel comfortable with the look to be able to pull it off and as long as it fits you will definitely be able to pull it off!
If it is a dress you are rocking or a mix and match print or it's not your style to show off some skin or you just feel the outfit will not go down well with your size, colour, prints, whatever it may be. Sometimes it's cool to turn up your style by challenging yourself to rock something out of the ordinary by putting the fab fashion trends to the test.