The best way to continue to wear a dress that you've already worn (several several times - like this navy blue dress above) is to change how you style it.
First, change up your jewelry - try a different metal, try a different length & style of necklace, or perhaps add a watch. Or a ring. Several rings?
Next, change up the accessories. Try a belt, or a scarf around your neck. Or a scarf AS a belt. Or, go without a belt, if you always wear a belt with said dress. Maybe you've got a hat that would look great with this dress. See how many different options you've got?
As for your shoes, I'm more of a flats/flat sandals girl myself, but I have been trying to throw in some heels and wedges. You know, to "up my style game." whatever that means... So, if you always default to the same pair, dust off the neglected ones that could really make your look stand out. Or the ones that perhaps you're too afraid to wear (a la "In Her Shoes"?).
While you're at it, try something different with your hair. Maybe with your makeup. I tend to repeat the same hairstyles over and over (and over. and over.), but I have been trying to break up the monotony that is my hairstyling skillzzzz with some braids and different parts. However, that's tough to do when I repetedly hit the snooze button and am rushing out the door to work...*cough*
See? If I was good at math I could tell you how many outfit options we've created, just with the few above additions and swaps. Alas, I am not very good at math, but it would be something to the something-th power, and that would be a lot of options to change up a dress you repeatedly wear.
So, go forth, and have yourself a stylish weekend, my friends!
shoes: Rocketdog via DSW