These classic black leather ankle boots will complement any ensemble, and easily transition from day to night thanks to the subtle almond toe and low block heel. $174.50, J. Crew. Havva.

gucci.com Pearl Shoes: Gucci Leather Mid-Heel Loafers For a celeb-loved pair you'll cherish for years, meet the Gucci Leather Mid-Heel Loafers ($1,150).