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Happy Birthday to DH! This pleated style skirt is a nice change from the tube style you wore last year. Since the skirt is flowy and has lots of volume, I'm thinking short tops and slim fit tops tucked in will work best and not compete with the skirt. Don't laugh, but those bodysuit style tops was the first top style that popped into my head. Or maybe a body con fit sleeveless mockneck top tucked in would work.
Great outfit! I love the sneakers with the skirt. It looks great the way you've styled it, but I have problems with that type of skirt too. I always feel like they emphasize my belly pooch and I can never quite figure out the right tops. You have lots of suggestions here and I hope you get it figured out because the skirt is great.