The only clothes shopping I do for my fiance is that I buy him a shirt every Christmas. For some reason, every year, there is a shirt he wants (that he doesn't mention until long after his July birthday) that he just never gets around to buying for himself. So we now have a tradition of him getting a shirt from me every Christmas. But it's always a shirt he has chosen for himself. I never buy him any clothing he hasn't already chosen.
When we went out looking for more work clothes for him a few weeks back, he surprised me by asking for and following my advice on his purchases. That's unusual for us. Neither of us has ever been overly concerned with the other's opinion of our wardrobe.