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This outfit started with the boots. Whenever I get something new I wear it to death for a while, and since I just got these boots last week, you’ll be seeing them a lot for the next few weeks. So I knew I wanted to wear the boots, and I also started eyeing my new (used, fake) leather jacket. Since both of those are edgier pieces, I decided to go with something more ladylike for the rest of the outfit to get some contrast, so I went with my houndstooth skirt and my favorite oversized button-up.