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I used the pictures you provided and think this outfit is very fashionable. You could mix up these pieces(or similar ones) to make many different outfits. A leather jacket, a nice pair of jeans, neutral shoes, and this shirt are all staples and won't go out of style. Everything is under $50, except the jacket. But good jackets are always an investment! I would say the jeans are perfect for you because apple body shapes look good in skinny jeans and hourglass figures look best if the waist band is curved, since it keeps you covered without gapping. I think the black boots would look best but I gave you three other choices since I know you still wanted to look feminine. If you want a pop of color I think the red scarf or hat (or both!) is a great way to get it. Ox blood is really trendy right now too! But that doesn't mean it can't be worn again for seasons to come!
I hope I was a help!
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