Bumping this thread some.
He definitely encouraged me to purchase my first corset, which I'm deeply glad for; he also has a fondness for them and can't keep his hands off me when I'm wearing it, haha. But in all seriousness, it's incredibly comfortable and I'm very glad he helped me choose it.
We both have the same kind of "fashion sense" - as in, jeans, t-shirts, and so forth. He wears tophats; I wear fedoras.
Whenever I dress up, he knows he's either in for a fun night out (or in) and it always surprises him to death whenever I go up to see him at work decked out in a dress or nice outfit.
It still tickles me whenever he tells me I look fantastic when I dress up for no reason; it still makes me melt when he hugs me in my crappier pajamas and tells me I look adorable. <3