Peri, I'm not the expert, but here's my take on it:
To me, gear has two meanings. The first is those things that are straight up workout wear. They are specialized clothes with a special purpose. You won't see a lot of folks sporting yoga pants and running shoes in WIWs because they are gear. Multi-pocket utility shorts and tevas? Gear. Hot weather survival outfits? A-okay fab even though gear. That kind of gear isn't a no-go (see Ariadne's post on her tennis shoes
here). It just isn't necessary a component that you would use to highlight your unique style. (Notice all the qualifications--this isn't a hard and fast rule.)
The second is more what I see Rae using it as. Gear can describe things that have a technical aspect to them, which can be used as a feature that highlights a person's style. So, for example, a reflective coating can make an item technically gear, but if worn in a very fashion forward way highlighting a person's sci-fi warrior style, it would be gear in the second way. Rae doesn't wear outfits that look like they were plucked from the shelves of REI entirely unaltered (gear 1), but she does wear her REI waterproof trench, which has definite gearish features and somewhat gearish styling, as part of her otherwise entirely urban outfits (gear 2).