My brother needs some wardrobe help. I've read Angie's posts on menswear and found them very helpful, but I need a little more direction. My brother is mid-twenties, around 5' 9" and very slim. He works from home and doesn't have much occasion to dress up, so his daily wear consists of flat-front khakies or loose jeans and flannel button downs or pull-over hoodless sweatshirts (bleh) in the winter, with white or black tennis shoes, and khaki or jean shorts with generic t-shirts or plaid button downs in the summer and the same shoes.

He doesn't look like a slob or anything, but he doesn't care too much about what he wears as long as it's clean. Most of his clothes are from shopping trips with my dad, who has good enough taste for himself, but I don't think the same look is really working for both of them! However, he's not really into the AE or A&F casual style that I dig on guys, so I'm not sure what my options are. I don't want to dress him as someone he's not, just tidy up his look and make it a bit more modern.

I'm thinking maybe fit has a lot to do with it? Because some of his shirts would be fine except for the fact they just kinda bag out over his pants after awhile, and being that he's so slim it starts looking geeky. I'm just not sure where to start!

So, what would be some good casual basics I can start his wardrobe fresh with? It needs to be comfortable and practical so he'll actually wear it, and stuff that he can just put together without thinking. He does need some new jeans so I'm going to jump on the chance and see if I can't get him into some dark-wash bootcuts for starters.