Punchy sneaker boot, $550, at Louis Vuitton, 919 N. Michigan Ave.; 312-944-2010, louisvuitton.com. Mister Pure watch, $115, at Swatch, 520 N. Michigan Ave.; 312-321-9670, swatch.com. Skinny flood jeans, $59.50, at Levi’s, 600 N. Michigan Ave.; 312-642-9613, levi.com. Triple-blade eShave razor, $60, at Skin1, 680 N. Lake Shore Dr.; 312-654-5452, skin-one.com. Prada Plex sandal, $750, at Barneys New York, 15 E. Oak St.; 312-587-1700, barneys.com. Big Boy flashlight, $39, at the Museum of Contemporary Art Store, 220 E. Chicago Ave.; 312-397-4000, mcachicagostore.org. Lucite necklace, $695, at Michael Kors Collection, 900 N. Michigan Ave.; 312-587-3600, michaelkors.com.

Photograph: Anna Knott
Styling: Jennifer Moore