Flat boots are my most-worn shoe once temps drop—comfortable enough for all-day wear but chic with denim, dresses, or layered looks. I look for cushioned insoles and a slim/tall shaft higher than the ankle bone. More boots I recommend also linked! bootie, ankle boot, fall boots, brown leather boots, brown leather booties, brown ankle boots, fall shoes 2025, fall boots 2025 LTKSeasonal LTKStyleTip