My first step is everyones fav! A staple pair of leggings paired with a tunic or longer over sized top. Something big and Baggy! The bigger the Better!! This is look is very comforting for days when you just want to hop back in bed.
Another trick are BIG bellbottom dance pants. Try to find a pair made of really nice quality fabric that you could possibly pull off as trousers for a classic look. Wear with a longer top ( can be fitted or not). These days you catch me in this look quite often. I live in a colder climate so I love pairing these pants with a man's cashemere oversize sweater to keep me warm and fashionable all day long.
These options are both 100% comfortable and can be dressed up or down with the perfect accessories. Adjust shoes, hat, and accessories to whatever climate you live in. If worn correctly these outfits can be ideal for any occasion.