[ultramarine]

Errrmm .. do it bit by bit ... If I were on your position Id start hiding his old tees .. the worst, tattered ones (and less favorite/noticeable) first until he just have a few limited options and throw him a new tee "Because you have none!" and one day when you are going out on a date or on a social thingie at the last minute ask him to change into the new tee or whatever ... try to do it ONE garment at a time and it generally works.

Or you just could band-aid it and store every single old tee and one day when he opens his closet he'll find the new ones :P

Please try to note what he wears and try to stick it ... I go quite often for the jeans + v neck tee (or dress shirt) + jacket which works for everything .. its kinda casual but dressy as well and almost no guy will mind it (the hardest part is to get him to love the jacket).

With my ex (Im gay) at the end I even got him to wear pastel polo shirts and loafers with NO socks. Twas a process .. but sooo worth it (I miss him .. boo!)