Go at him for not being as luxe as you.
How to do it: "Yo, nice new blazer. I saw the sale rack at J. Crew too."
One of the best backhanded compliments you can throw at a stylish guy is that not only can you name who makes his "luxury" stuff, but you also know that he bought it because it was at a deep discount. Dudes who wait 'til something is 80% off? Definitely not luxe. He'll feel ashamed immediately for not being able to shop at your level.