Sunday evening in Chicago called for an outfit that was effortlessly chic but cozy enough for lingering over cocktails—an oatmeal twin set paired with a taupe silk midi skirt that swayed just right with each step, knee-high brown boots for that perfect mix of style and practicality, and her go-to gold necklace with coordinating herringbone earrings for a little extra shine. The night was one of her favorites—a monthly tradition with some of her oldest Chicago friends, starting with a cocktail at Sportsman’s Club, then a glass of wine at Nettare, and finishing with a standout dinner at Lao Peng You. The kind of evening that reminded her why she loved this city, the friends who felt like home, and the magic of a Sunday well spent. LTKParties LTKWatchNow LTKStyleTip

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Adaline Riding Boot - Brown | Jack Rogers
Gwyneth slip skirt | J. Crew US
Sweater shell | J.Crew Factory
Classic cotton cardigan sweater | J.Crew Factory
Herringbone Chain Necklace | Ring Concierge
Double Herringbone Chain Dusters | Ring Concierge
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