32 Chic Tops That Will Instantly Command a Second Date

Whether it's your first date or date number 50, anything that streamlines the getting-ready process and removes the pressure of a special night outfit-wise is a win. Let's be honest. There's nothing worst than the panic of realizing you have nothing to wear five minutes before you're supposed to leave, (I know the feeling all too well!) That's where having a solid rotation of go-to date-night tops comes in handy. Just grab your favorite black pencil skirt, elevated jeans, or miniskirt, and voilà—you're ready to head out the door.
I've curated a selection that caters to every mood, vibe, and budget, from bold velvet pieces to laid-back, effortless sweaters. Whether you're looking to impress that special someone or keep things flirty yet casual, I've got options for every type of night. The best part? I'm sure these are guaranteed to get you a second date. Below, shop my favorite picks for date-night tops you won't want to miss.

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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