I can't stress enough that sometimes you just have to try it. Make combinations that you never thought of before. Take a jacket and try to pair it with every shirt you own. Some won't work, but you might be surprised how many combinations you can make with clothes you already have!
Military jackets are my favorite because they are SO versatile! You can wear just about anything with a military jacket. In the outfit below I'm actually wearing a turtle neck with a turtle neck on top and then layers the military jacket on. It took 2 average looking shirts and made them interesting!
Another item of clothing that is super easy to change up is skirts. Challenge yourself to pair it with a unique shirt. You never know what could happen! You could layer it with a cardigan, pull on a sweater, or add a jacket. Wearing a cropped top with a high-waisted skirt is a personal favorite of mine. It's different and gives of a casual vibe while still looking feminine and poised.

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