The answer is, it depends. While some of us would not be caught dead in a Salvation Army store (although we are more than happy to donate, of course), there are a few looks that can jive with the bargain basement look. The key, as always, is moderation.

Take Chris Martin, for example. Musicians were the original purveyors of the sloppy look. As legend has it, the musicians were more interested in spending their hard-earned cash on CDs and tickets, not clothes, so they had to do their shopping in the cheapest places possible. That M.O. has turned into a full-fledged trend, but like any trend, it needs to be tempered with common sense. What Chris has done is a reflection of that. He's followed the first two rules of the casual male: 1) random tee shirt, 2) no-work haircut. Most importantly, his no-care wear is not well worn, not messy. Casual does not equal sloppy.

Someone forgot to tell Mary Kate Olsen. Now I know a lot of people pick on poor Mary Kate, but let's be honest here - she has blurred the line between casual and bag lady. Here's what's wrong with this outfit. Firstly, too much of any one quality in an outfit can ruin it. If you wear an all-orange outfit, you will be sure to draw some pumpkin comments. So what her problem here is that everything she's wearing is too big: the bag, the scarf, the sweater - not to mention that in addition to the huge sweater she's wearing she's carrying yet another, so you know she's not done being sloppy. If you're going to wear a big sweater, wear fitted jeans. If you're going to wear baggy cargo pants, pair it with a camisole. In addition, no matter how sloppy you are feeling, fix your hair. I don't mean blowout and style, a nice chignon is a great way to hide a bad hair day and not look like you are. As a final note, Mary Kate, I know you struggle with your weight, but don't hide it. Own it. Wear clothes that fit appropriately, and if you are truly unsatisfied with how you look, eat a sandwich and be proud when you get to a place where you are happy with how you look.

Now let's look at Ashley. No, not MK's sister - Ashley Judd. Ashley's at a sporting event, no better place for a casual outfit. She's already following casual rule #1, but the shirt fits very flatteringly on her body, so she doesn't look frumpy, she looks cute. She's also put a barrette in her hair so there's a little girly-girl underneath that tomboy exterior. She's also adhered to an important maxim of the casual female - she's wearing makeup, but it's not overpoweringly obvious. She's well put together, but she's avoided looking high maintenance, which is key when you're going to something like a basketball game with your sweetie. It's the Something-About-Mary rule: a girl who's fun to hang out with is a girl men like. It's like gaining a friend, not losing the opportunity to hang out with his friends. But remember - all in moderation. Don't hesitate to whip out that little black dress when the proper occasion calls for it!