Jean-Luc definitely knows what he likes and feels best in, and he wears it to make a good impression with his ladies.
The left caps, with Beverly Crusher, feature a doppelgänger, but he’s wearing the clothes in Jean-Luc’s closet and that blouse is either nearly the same, or actually the same, shirt he wears while wooing Nella Daren in the right caps.
And this green blouse is either nearly the same or actually the same as the one he wore on vacay with Vash.
Finally this, worn again with both Nella and Beverly, is definitely the exact same shirt.
Jean-Luc is deliberate in his choice of what to wear on a date. He’s going for the ‘soft romantic gentleman-scoundrel cover of a romance novel’ effect: comfortable silks in eye catching hues or patterns that emphasize his chest and waist.