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I don't think you can stylize a sweatshirt (try as you might). Sweatshirts are usually too bulky and too warm to be... are we talking about looking chic with sweatshirts? Because if so, that's almost impossible. One would be trying too hard to be stylish with terry sweatshirts better left for going to the gym on cold days. However, you may design a sweatshirt with feminine touches. For example, you may have puffy sleeves around the shoulders and forearm and just make the rest of the sleeves in some other special way. I just don't see dressing up sweatshirts in any such way.
There is no such thing as dressing "too pretty" or "too dressy." I think one shall dress however they please. I really get tired of the "don't look so girly" thing. It's like with gladiator sandals- not supposed to be cute, but not stylish either. The skirt (or is that a dress in Post #5) is fine. I'd get rid of those sneaker pump-like boots and especially the sweatshirt. I'd probably replace the sweatshirt with a dressy blouse or top. A regular T-shirt with a stretchy shrug or bolero jacket would work better than trying to style up a sweatshirt. Kind of funny that these fashion track pants and hooded jackets are pretty much fair to me, but sweatshirts aren't. And if you're going to have something athletic to offset anything lovely, just go with one of those athletic-style silver T-shirts than sweatshirts.
And remember... different doesn't always mean better.
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