I usually wear T-shirt with jeans.
And then wear white socks with sneakers!
And when I go to meetings or preaching, I wear dress and high heels!
It looks cool and nice!

“Kindly forgive and comfort him, so that he may not be overwhelmed by excessive sadness.”​ — 2 Corinthians 2:7
=
I usually wear a T-shirt with jeans.
And then I wear white socks with sneakers!
And when I go to meetings or to preach, I wear a dress and high heels!
It looks cool and nice!
= "T-shirt" and "dress" are singular countable nouns, so they need an article such as a when referring to one in general.
= Great job!