One of the most fashionably stressful events in a woman's life can be, hands down, meeting the parents of your boyfriend or girlfriend. No matter how old you are, now matter how long you've been dating, it's practically impossible not to revert back to your slightly insecure 15-year old self. You want to make a good impression, have a good time, show the family what a fantastic partner you are to their child, etc. etc. And you want your clothes to help reflect all of these things. A pretty tall order for one outfit.

No matter what you're doing with the family - meeting for brunch, getting together to watch a football game, having a cozy night in at the family home - keep a few tips in mind as you get dressed.

Dress for the occasion without overdressing; don't wear heels to a football game unless you want the family to call you High Maintenance Heather behind your back.

Show your personality while complementing your partner's style - although I am definitely NOT suggesting you wear matching outfits. Don't do that.

Wear an interesting accessory - your great-grandma's favorite necklace, a chunky cocktail ring, red shoes. If nothing else, it could serve as a conversation piece during those inevitable awkward conversational lags.

Keep makeup natural - let the family get to know you and your face before bringing out the smokey eye.

Here are a few of my favorite meet-the-parents looks:

Great for dinner, either out or at the family estate.

Darker-wash jeans with trouser details (look closer at the stitching and seaming on this pair) are usually a safe bet, no matter the activity (unless we're talking fancy dinner, obviously). You'll look casually polished.