I really like DBF's style - but he is color-blind with certain shades of blue and green. So very occasionally I have to run interference, so that he isn't walking out the door in head-to-toe olive or khaki. Sometimes he hits the "Daniel Craig as 007" casual-wear look spot on, and I wax rhapsodic over this. But otherwise, he is very good about culling his own stuff.
With my ex, I did have to cull his wardrobe. He was military, and when he wasn't wearing a uniform, he still had to adhere to a civilian dress code, as an officer living overseas. With the result that everything else just got pushed to the back of the closet. In the mid-2000's, I had to purge several silk shirts that I am pretty sure were 'in' when Miami Vice was on prime-time television, and a suit from around 1990 that vaguely evoked M.C. Hammer's "Can't Touch This". He also had two shirts his mother had given him that were gingham, and looked like they belonged on tables in a small Italian restaurant.
I didn't ask. I just did it, and he expressed his relief and happiness later.
Don't let your loved on walk out the door looking like an 80's icon, or wearing Hammer pants. Purge and cull.