RachyLou, what a great question ! I absolutely think that you can. I look at so many young bloggers that wear similar outfits right down to the accessories and I never tire of how they look.
As for me doing it, I have a harder time. It is a bizarre dichotomy for me. I have no qualms being somewhere and having someone else in the same outfit. In fact, I would have no problem at a YLF get together if the other ladies and I were all in similar, Angie approved outfits. Yet at times, I feel oddly uncomfortable pangs of looking or having something like everyone else. For example, I have a Longchamp bag that I LOVE and I bought the same bag, same color in a larger size. I had not had a chance to use the larger one before the Boston get together. In Boston, I saw large Longchamps bags EVERYWHERE. And I saw many, many in my beautiful Billberry color. I decided to come home and return mine because it was everywhere in Boston. I was inexplicably disappointed. But then I needed it for Hawaii and used it daily there. And I did not see one other Longchamp....and I rarely see them where I live, so I decided to keep it. It isn't that I feel less stylish but rather uninspired, I guess.
I also felt this way one day at a mall over the winter. It seemed like every female in there had on skinnies tucked into boots. Most boots were cognac or tan, mine at least were black. But I felt disheartened.
Maybe I am ok in a more intimate situation when I know people or can approach them. But in a large, impersonal crowd in bothers me. HA ! A revelation...now to figure out why in God's name it happens that way....