I'll admit, I do care about fashion. I'm not exactly what you'd call trendy, though. Since I have no sense of where different dress codes apply, all my clothes are somewhat dressy. I feel like a slob in sweatshirts, so I guess I usually appear somewhat put-together. I've been told I look like a stereotypical french girl (whatever that means?)
My jeans are all some sort of dark color and I wear a different blazer almost every day over various t-shirts or girly blouses. It transgresses into work, play, class, everything. And all the colors are pretty neutral, except for my shirts, so it all goes together. I love sneakers too, but not the type that look like running shoes. If I feel like it I'll wear giant sunglasses and carry a giant purse and pretend I follow trends religiously, but honestly I don't have the patience.
If something is comfortable but not too baggy where I get lost in it, then I'm happy. I think it's okay to repeat similar outfits as long as your clothes are timeless enough to not make you stand out like a sore thumb.