Cozy, casual, and still pulled together—this is my go-to kind of outfit for errands, school drop-offs, or a casual day out. I love layering a striped hoodie under a sherpa jacket for warmth without bulk, and olive utility pants always feel like a neutral that works year-round. Finished it off with comfy sneakers and a bold red bag to tie everything together. This is one of those outfits that looks styled but feels like loungewear—and I’ll take that win every time. Everything is linked here on LTK so you can recreate this easy, everyday look. Shop the look: sherpa jacket, striped hoodie, plaid layering shirt, olive pants, casual sneakers, red crossbody bag ⸻ casual winter outfit, women over 40 style, everyday casual outfit, sherpa jacket outfit, striped hoodie outfit, olive green pants outfit, comfy mom outfit, casual layering outfit, athleisure inspired casual look, winter errands outfit, red handbag outfit, sneakers for everyday wear, transitional winter outfit, relaxed weekend outfit, closet basics outfit LTKSaleAlert LTKootd LTKFindsUnder50