Fill a cocktail shaker with ice. Add pineapple juice, lime juice, orange sec, and pineapple habanero vinegar. Shake vigorously, until the outside of the shaker is chilled, 10 to 20 seconds.
Rim you glass with agave or simple syrup then dip in Tajin. Strain cocktail into glass. Garnish with pineapple wedge and lime wedge.