Gentle Souls ankle booties - a top pick of mine from Nordstrom’s Anniversary Sale and still in stock I got black last year and loved them so much, I hunted down dark brown and mushroom as well. 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 Ella boot) but looks and feel nearly the same. LTKxNSale LTKshoecrush LTKsalealert