I love this thread, and unfortunately don't have much to add, but I'd like to give you all a glimpse of my boyfriend's sense of "style" (in quotes because it's about as far from real style as you can get!).
Disclaimer: he works in the most casual office in the world. (Really. The only rule I know of is "no bathing suits.") And he has indeed confessed to me that he would not take a job that required anything above business casual.
He owns a boatload of tshirts, most of which are too big. Lots of logos (he works down the hall from the marketing department). He owns about three long-sleeves, purchased solely for a trip to Alaska to see my family. He claims that anything other than tshirts in summer, fall and spring make him too hot.
Shoes are worse: he only owns five pairs, and two of those pairs I made him buy for special events we had to attend. (They sit in the closet 99% of the time.) The other three pairs are Tevas for the summer, high-top Converse, and New Balance "grandpa" shoes. Are you getting the jist of this? HE IS HOPELESS!
Here is the kicker: HE WEARS JORTS. Jean. Shorts. Always Levi's. Purchased in the boys' section because he is very short (5'6") and skinny. To my utter horror, he actually bought some full-length jeans and then shortened them himself! With a denim needle and contrast thread! It was painful to watch. He does have a few pairs of Levi's full-length jeans (also purchased for Alaska), and he looks great in them, but it requires much prodding on my part to get him to actually put them on.
He owns three pairs of khakis, none of which see the light of day unless we are going somewhere requiring an ensemble that does not include denim. In a sad twist of cruel fate, the most expensive item in his closet is a pair of J.Crew khakis, purchased under my watchful eye, and they make him look so put-together and smart, even with just a solid color tee. But he hates wearing them.
I have tried and tried and tried, but he refuses to budge. Absolutely, staunchly will not bend. I have pretty much given up on him trying to modify his wardrobe.
Anyways...sorry to vent on this thread. But I wanted you all to know what I have to deal with. It's sometimes hard for me to be stylish when he is so UNstylish. But alas, to each their own, and if what he wears makes him happy, it's alright with me. (Except when we're going to weddings or other social events!)