We have all experienced the unique anguish of planning an outfit for introduction to our significant other’s parents. One thing I’ve learned over the years of meeting parents is that you don’t want to call attention to your clothes: stay away from statement items, bold colors and eye-catching materials. You want to showcase your lovely personality (and good posture) on that crucial first meeting, not have them asking “Why is our child with this… carnie… in leather chaps?”

However, it’s also important to be natural and not wear the sartorial equivalent of a sign that says “I swear to whatever god you believe in that I have never done anything I regret in my life. Ever. Each night I sew your son into a roomy flannel onesie and then we discuss our eventual move to hand holding, which–I promise–is still a ways off.”

The outfit planning can be particularly nerve-racking if you don’t have a good gauge of how old fashioned they are. At a certain point, you do have to say ‘fuck it,’ because if they’re going to be all, “Well, I never!” because you’re wearing jeans, then you’re never going to please them and they’re jerks.

But… chances are they’re the kind of people who will be pleased and impressed if your outfit is like a softer version of a job interview ensemble. Pencil skirts, cardigans, tweed jackets and knee-length floral dresses are your best bets. Consider adding a strand of pearls. Here’s our gallery for what to wear and a few looks to avoid.

[ITPGallery]