Reposting since My most walking friendly, comfortable low ankle booties are back and on sale • Gentle souls 5.5 boots Size up if between sizes. I’m usually a 5 to 5.5 and went up to 5.5 since the front toe felt a little narrow. These have a cushioned insole, flexible rubber outsole, and a slim stretchy ankle shaft that works perfectly tucked under jeans and pants or with tights. Note: this boot comes out in new iterations each year with a different style name, but I’ve found them to all be extremely similar. My 3 pairs all have a different style name (ie the Emily, Ella boot) but looks and feel nearly the same. LTKSeasonal LTKShoeCrush LTKStyleTip

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Women's Emily Zip Mid Heel Boots | Bloomingdale's (US)
Elly Bootie (Women) | Nordstrom
Paige Bootie (Women) | Nordstrom
Dusty Bootie (Women) | Nordstrom