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How much do you like this person?
I think your outfit sounds like office casual Friday. Maybe change your loafer for cute boots or something nicer. If I’m really interested in the person, I wear a V neck blouse or a color that complements my undertones.
Avoiding wearing booties / heels because he’s on the shorter side 😆
Would swap loafers for heels or booties. I usually wear a sleeveless solid blouse with fun earrings and or necklace.
Mom jeans flatten your butt. Keep your ass-ets.
Silk blouse with one more button undone than you would do at work? Fun pattern and big earrings?
Check out “the Motherchic” on Facebook or instagram. Not sure if you’re a mom or not, but that’s really irrelevant here. She posts some great date night looks that might give you some ideas. Personally I think she wears too many ripped jeans, but that’s a simple swap.
Pro
My go-to is low heeled pointy booties, flattering black jeans, cute slimming top & leather jacket or cute casual oversized blazer