I've recently found this series of videos on how to style various basic items 10 - 20 ways. What I like about them is how she classifies each look - street style, preppy style, etc - so that it's enjoyable to see how she tweaks each outfit to represent modern iconic looks, or lewks, at the same time keeping a very small wardrobe. A different kind of versatility than just dressy, casual, etc. I just linked to the one on culottes (wide leg pants) but she does button shirt, midi skirt, maxi dress, shirt dress, tee shirt, etc. Thought this fit right in with the shop your closet challenges.
Alyssa Beltempo is the youtuber