You can look smart and can dress well if you select your outfits that matches to your personality. You should also take care of colors while selecting an outfit for you. Beside this you should also know what exactly suits you.
Realize you can still keep your personality and style. If you tend to dress frumpy or older than you really are you'll need to let go of your comfort zone and be willing to try something new.
Choose the most comforable way, when you are not feeling you are dress,then you find your perfect clothing.
Why not give yourself permission to go to the shops and just try anything you like.then,shopping online what you are interested in.My old sister bought her occasion dress on nissenbridal.com, It was beautiful. I am also ordering from a similar company. You'd better to be very careful and look closely at feedback. Also be very upfront and clear with them since a lot of the time they make the dress from sketch to fit your measurements. Good luck!