In general, men develop their look after college or once they've established themselves in a career. Then they tend to sort of wash their hands of the entire building a great wardrobe idea and just buy the same sorts of things repeatedly, year after year. Their look does not evolve with the times and they are sometimes pretty prickly when their partner suggests an update.
When I moved in with my then-fiance, I remember spending a couple hours going through his wardrobe. He knew me well by then so was not surprised at my eagerness to engage in a bit of Wardrobe Wisdom. Still, he had an excuse for keeping every absurd, outdated, ill-fitting garment in his closet. Oh, the baggy, ugly patterned harem pants! Oh, the skinny knit ties! Oh, the fanny packs! I remember laughing a lot and him finally going along with my suggestions to chuck several things. Still, he held onto those pants and one of the fanny packs for awhile!
Today he asks me for wardrobe advice and allows me to do most of his clothes buying. Over the years he has come to appreciate my motto (thanks to Tim Gunn) of buying once and buying well. When he received a promotion recently, we talked about how this meant dressing for his new position, and he finally purchased a beautiful dark suit and some timeless gray slacks. He would much rather spend his money on Apple products or bikes, but he does see the value of dressing well.
I am not suggesting that you laugh uproariously at your partner while going through his closet. My husband was an exceptionally good sport. What I do suggest is that you show him some pages from current men's magazines or clothing catalogs that you like, telling him how handsome and dashing he would look in similar clothing. Let him know you are delighted to do all the shopping (or let me or a personal shopper at Nordstrom do it for you) and slowly introduce a few new items into his closet. At the same time you may, very gently, ask him if you can box up some of the outdated items he no longer wears (or shouldn't be wearing!). Assure him these things are not being eliminated, just moved out of the closet to make room for clothes that look great on him NOW.
I have had to be patient with my husband, mentioning a shirt or sweater I saw that would look good on him, or suggesting he get rid of some things he no longer wears. Sometimes he gets defensive and wears things I don't favor, such as his riding knickers, but overall I have seen his confidence grow as his style has evolved. He feels good in his clothing. So have courage, women, and don't give up!
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