Dressy casual outfits party

Discover Pinterest’s best ideas and inspiration for Dressy casual outfits party. Get inspired and try out new things.
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a woman wears an old money style black lace dress for dinner date night

Old money style is all about timeless silhouettes, understated elegance, and knowing exactly how to dress for the moment. These 25 outfit ideas are perfect for dinner nights, whether it’s a first date, anniversary, holiday evening, or just a casual night out. From tailored trousers and chic dresses to polished yet simple pieces, these looks feel refined and relaxed all at once. The kind of outfits you’ll reach for again and again when classy is the goal.

a woman wears a mauve off the shoulder wedding guest dress

Not sure what to wear for a casual dinner date this spring? These 15 outfit ideas are the perfect mix of relaxed and romantic—think sleek jeans paired with heels, breezy spring dresses, chic sneakers, and elegant layers that feel effortless. Whether you're heading out for a fancy dinner, a night of casual cocktails, or a cute springtime stroll after your meal, these 2025-ready looks keep it classy, stylish, and totally date-night approved.

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