It may be a case of life imitating art, or maybe its art imitating life—either way blonde beauty Blake Lively has a man and wardrobe sparking envy from women everywhere both on-screen in the mega hit Gossip Girl as well as off. With boyfriend Penn Bagdley always by her side, Blake has been looking more radiant, confident, and gorgeous than ever. And thanks to many public appearances and tons of leaked Gossip Girl images, we’ve been treated to a vast array of date-night outfit inspiration. Here are three of my favorites, after the jump….

We discussed the horrendous implications of wearing too-tight leggings that give you camel toe. But now there’s an alternative that does just the opposite! New low-crotch leggings give you the flattering look of just having taken a big poopie in your panties. Get them at Karmaloop.com for the super low price of $82. [Karmaloop via StyleHive]

Ashlee Simpson has had her share of hits and misses in the style department, from her days as a wild punk rocker (miss) to her transition to a buxom blonde (hit), and hundreds of other looks, hairdo’s, styles, and so on in between. However, ever since she hooked up with Fall out Boy lead singer Pete Wentz, Ashlee seems to have come into her own and developed a unique signature style that is a part punk, part sexy vixen, part avant-garde trendsetter, that suits her to perfection (come on, you know you kind of hate yourself for it, but you have to admit you’re kind of starting to envy her style!). In pictures of the two, Ashlee looks absolutely radiant- serving as further evidence to the universal truth that feeling good is the most essential ingredient to looking good. For my next ‘date night’ edition, I looked to Ashlee for inspiration. She always looks confident, happy, sleek, and never overdone.

“First date” - two simple words that can send shivers up anyone’s spine, much like the words “job interview.” When you think about it, there isn’t much of a difference between the two, except one involves cocktails and palpable sexual tension. I have no idea where that old adage “You are what you eat” came from, because the truth is, “You are what you wear.” Clothes speak volumes and no matter what, they will always prompt judgments from others. Chances are, the person you’re into isn’t going to notice how perfectly your bangles play into the boho-chic vibe you were going for, or how you expertly coordinated your makeup shades to play up the metallic sheen outlining your top. Guys don’t notice the details, but they do see the overall big picture. Here are some general tips to follow before any date, after the jump…

Oh the joys of getting dressed before a date—the plotting, the scrutinizing, the constant need for re-assurance from your friends that you look hot and not in any way slutty, the hours in front of a mirror, the Polaroid pics (how can anyone forget Cher’s over-the-top first-date precautions in Clueless?)…

Maybe you don’t go quite as far as these extremes—or maybe you go embarrassingly beyond—the point is, any girl would be lying if she didn’t admit to at least a slight amount of neurosis regarding this process. But lighten up, ladies, because as I recently discovered, sometimes the perfect date-night outfit can emerge accidentally on its own.

Last time we set the boundaries for what a first date outfit should entail. Remember, the look should reflect who you are, shouldn’t give it all away (too tight, low cut, and too short are NO-NO’S), shouldn’t appear as though you tried too hard, and conversely, like you didn’t put any effort into your look at all. The outfit I devised to meet all these guidelines included jeans, a flirty top, a blazer, and boots. However, this might not work for everyone—say, women who LIVE in dresses (as many of my friends do). A dress does not always have to indicate high-maintenance, and finding a dress you love and building upon it with fabulous accessories may result in that ever-so-elusive understated sexy, laid back, fun to hang with-vibe that is guaranteed to keep him transfixed by you. Just check out the look sported by Anne Hathaway!