ELI5 how to select and wear my first pair of ankle boots

I’m looking to upgrade my shoe game and I’m lost. I’ve been wearing DTC plastic flats (Rothy’s etc) for ten years. I recently expanded to a pair of Ecco Soft 7s in a dove color and my wardrobe world got rocked. I bought my toddler a pair of zip up yellow booties and her toddler chic game is on. She’s got me jealous and thinking about ankle booties. I have never even tried on a pair of boots that weren’t rubber. I am so new to styling anything other than flats and was hoping to get some recommendations of features to look for or to avoid. There’s so many choices.

I’m 5’ 6” and skinny, mostly rectangular. I’m an executive that works in an in-person, biz-casual office (but I always dress on the business side of that range). I wear a lot of knee-length skirts / dresses, with tights and pantyhose because offices are always too cold! Lots of fit and flare or fitted silhouettes. Haven’t really gotten into the wide leg trend — most of my pants are narrow at the hem. I live in a place with mild winters. I’m a winter, wearing mainly jewel-tones (including colorful prints). I don’t wear high heels often and imagine I’m looking for flat or <1” heel, low shaft booties in black or brown… but I have no idea what I’m doing. I would love your recommendations and any go-tos — as well as any advice!

Also, are booties only a winter thing or do they work year round?