I'm super guilty of wearing these polka dot trousers from Old Navy to death. I swear I wear them once a week, because both black & white and polka dots are super versatile and just go with everything. I've paired them with buffalo plaid, florals, stripes and even a basic cropped sweater like this one from Banana Republic. There are certainly times I think "I don't want to feature these again, people will think I only own one pair of pants!", but a big part of being authentic is admitting that I am a chronic re-wearer, especially in the fall and winter!
Sweater|Banana Republic Trousers|Old Navy Shoes|Jessica Simpson Bag|Coach Glasses|Vintage