My T complimented me on my boots recently too
I see T on my day off, and am typically too lazy to get dressed up very much. Which means I often go in jeans and a t-shirt or sweater. I feel mixed about fashion in general. For the most part, I don't really care what I wear, and would probably wear the same thing every day (clean, of course) if it were socially acceptable. But sometimes I feel pressured indirectly by the people I associate with - some of my friends and definitely other parents at my kids' schools - to be more "with it" in terms of fashion.
I don't think my T really cares what I wear. And if she does, I'll try to convince myself that I don't care that she cares

Interestingly, she commented on what she was wearing one day, saying it was her "casual, errand running outfit," because she wasn't seeing many clients that day. Must have been close to a holiday or something. I hadn't noticed anything different about how she was dressed.