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English Factory English Factory Off-Shoulder Gingham Long-Sleeve Midi Dress Current price: $95.00 From Anthropologie Loading Inventory

Clean, minimalist silhouettes from Ralph Lauren, Solace London, and Norma Kamali underscore the inherent elegance of black, allowing the focus to rest not on the dress, but on the woman wearing it

This dress also features a low back design that shows just the right amount of skin

She did not approve of all these colors

Avoid too-busy prints and, of course, creams and light colors that read as white

MTV-Ready Flannel Shirts Flannel shirts werent invented in the 90s, but their association with the eras grunge scene forever lends them an aura of counter-cultural cool