When you're outfit-planning for a date with someone other that your TV and that Bravo marathon, it's okay to try a look that's a little — dare we say it? — trendy. We know you're loving fall '11 trends, but if they feel a little un-Chicago, we feel you. And we can help. We know Chi-town style is a little less throw-caution-to-the-wind daring than the life-sized runways that are the streets of New York. This is a good thing! We like, no, love, your style, and we've found 10 brand-new dresses that celebrate it. These flirty dresses toe the line between fashion fearless and insane in the best possible way. Seriously, you'll feel hot in every single one of them. So, go forth and rock a trendy frock comfortably, and with confidence. And leave all of the ensuing compliments that ensue in the comments, pretty please.