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Hee. My fiance would love to pick out a wardrobe for me. He pouted when I told him my wedding dress was going to be a secret because he wanted to help design it!
He is very stylish, and I am probably the "What Not to Wear" candidate. I love my sweats/jeans/T-shirts. (But I'd never go to a wedding dressed in them!)
Pretty much every guy I've ever been with has been a "What Not To Wear" candidate. Hmmmm....what does that say about ME, I wonder? 
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I was just talking to a friend about our husbands and their wardrobes. She buys all of her husband's clothing and picks out his outfits for formal events. If it were up to him, he'd wear t-shirts and basketball shorts 24/7. My husband, however, has a really good sense of style and enjoys clothes shopping. I buy him clothes as gifts but he usually chooses what he wears all the time.
Is your SO a clothes-horse (like mine) or would he be a candidate for "What Not to Wear" without your help?