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What to Wear When Meeting Your Boyfriend’s Parents This Holiday Season

Look great so that you feel comfortable meeting the fam!

“So . . . do you want to spend Thanksgiving in Philly with my family?” I’ll never forget that moment. We were in a darkly lit New York City speakeasy on only the third date. I sat there openmouthed and then sputtered out, “But . . . but . . . you haven’t even officially asked me to be your girlfriend yet!”

OK, so maybe most people don’t get asked to meet the parents before even defining the relationship, but I have to give my now-husband some credit for being sincere, intentional, and ever-practical—Philly was only a short train ride away from my at-the-time home base of NYC. Needless to say, he did ask me to be his girlfriend, but I also understand every girl’s feeling that meeting the family is a big deal—a huge step from just “dating” and getting to know one another.

Which obviously brought up another very serious question: What do I wear?

Nailing the perfect outfit isn’t as elusive as it may seem. First up: Know your environment, and do some sleuthing. Ask your boyfriend what to expect on the holiday. Is his family the super-casual type that lounges around all day and watches football on Thanksgiving? Or do they make it a fancier affair with a white tablecloth and hours of engaging conversation around the table? This makes a difference between wearing jeans and your favorite sweater or a classy dress and tights.

When you’re walking into unknown dress code territory, the safest bet is a dressy–casual mix, and here’s how to do it. Basically, you’re going to dress down a dress or dress up your denim.


You want to look feminine, put-together, and appropriate, so a knee-length day dress with sleeves and a bit of flounce is perfect. An A-line silhouette, which narrows at your waist and flares out slightly over your hips, is the most universally flattering fit. Or, a modern shift dress that falls straight over your form is another winner. Pair with tights, and slip on your favorite booties in a medium to low height—three inches or lower. You don’t want to be awkwardly teetering around, no matter how cute those boots are.


If you’re more of a jeans gal, you can totally wear your fave denim. But go for a dark wash, and pair it with a dressier top, such as a pretty long-sleeved blouse or a cashmere-blend sweater (even better with a bit of embellishment, if that’s your thing). Again, throw on booties, the perfect dressy–casual shoe, or nice flats, and play up jewelry with earrings or a sparkly necklace. This look makes you really approachable, which is great for a family gathering, while still looking classy to impress his parents.