Even if it’s a mani at Chill House, a matcha with the girls, and a quick browse at Barneys Downtown—it still counts as errands! A lace top and paperbag-waist pants will ensure that you’re as chic as you are comfy for scooting around town, and a spacious tote means there’s room for a bit of shopping.

ULLA JOHNSON Oksana Flutter-Sleeve $230 $139 / ULLA JOHNSON Agata Cotton-Linen Paperbag-Waist Pants $265 $159 / LOEFFLER RANDALL Rubie Striped Suede Slide Sandals$350 $209 / BARNEYS NEW YORK Leather Tote Bag$315 $229


A rowboat in Central Park, mini golf at Chelsea Piers, oysters at Maison Premiere—spending quality time in the light of day with a special someone has an allure all its own. Since day dates are often active, you’ll want to be comfy, so balance a shorter hemline with cute flats, and bring a bag big enough to haul some makeup for touchups as evening approaches.

JOURDEN Embroidered Fit & Flare Shirtdress $645 $259 / CHLOÉ Faye Medium Shoulder Bag $2990 $1499 / ISABEL MARANT “Leakey” Metallic Leather T-Strap Sandals$505 $349 / ISABEL MARANT Kinley Belt$280 $109

It’s rooftop season, and the biggest decision is which one you’ll be on sipping rosé as the sun slips behind the horizon. Whether you’re in Brooklyn at Westlight or in the city at The Delancey, a flatform and clutch and will take you smoothly from sun up to sun down.

PROENZA SCHOULER Striped Abstract Jacquard Crop Top$1090 $439 / EACH X OTHER Embroidered Crop Jeans $405 $199 / VALENTINO Velvet Double-Strap Platform Sandals $945 $569 / LOEWE T Large Pouch$1150 $689

To master looking relaxed and polished all at once, look no farther than a nuanced shirtdress paired with sneakers that shine. Just add a mini cross-body, and you’ll be ready to conquer a sun-kissed Bloody Mary sesh.

OSMAN Striped Cotton Belted Shirtdress$970 $389 / SAINT LAURENT Women’s SL/39 Glitter Platform Sneakers$595 $239 / BARNEYS NEW YORK Suede Camera Bag$225 $159 / CHLOÉ Tassel Bracelet $290 $149


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