[He chuckles at her dodging his little self-disparaging joke and trying to compliment him anyway. It's just a little funny.]

My boy tried to look like that kind. I guess he pulled it off with how many women he got mad at him. [He shakes his head at his little dumbass. His little dumbass who is several inches taller than him but still his boy, wherever he is.]

I had this thing tailored so I'll thank ya for the compliment. [He assumes the compliment is for the fashion sense rather than, you know, him.]