The boots I wore all around NYC that were actually really comfortable! They are no longer available, but they are Steve Madden - I linked two extremely similar options from there & then another similar brand! Loverly Grey, black boots, black booties, New York outfit LTKSeasonal

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DUSTY Black Leather Women's Ankle Boot | Steve Madden (US)
DARSEN Black Leather Square-Toe Block Heel Women's Ankle Boot | Steve Madden (US)
George Ankle Boot | Matisse Footwear
Hstyle 6 Pairs of Ruffle Socks Women, Cute Ruffle Ankle Socks | Amazon (US)