What to Wear for a Night Out

My parents love to complain that I never go out. In fact, during our last phone conversation, they very subtly (or maybe not so subtly) suggested that I’m a shut-in. Wanting to prove to them that I am, in fact, a fun and outgoing person, I announced that I was going to the opera on Wednesday. And a pretty hip concert the following week. Mollified, they hung up, and I instantly started to feel frantic about what I was going to wear. So, after throwing all of my clothes onto the floor and assessing every single piece (a bit dramatic, I know), I’ve come up with a go-to outfit for the events I'm most likely to attend, even if I'm attending them simply to prove a point.

To save you the trouble of throwing all of your clothes to the floor yourself, I've decided to share the outfit ideas I've come up with. I hope these help you the next time you have an "I have nothing to wear!" moment.

What to Wear to the Opera

Wanting to keep the promise I made to my parents, I found myself with two tickets to the opera. Well, by “opera,” it’s more or less my son’s daycare putting on A Christmas Carol…the abridged version, and he’s playing in his breakout role as a lamp. My husband and I were in our evening best: his dress pants and a plaid dress shirt tucked in, and me with my black Ponté dress, tights, and ballet flats.

Whether it’s a legitimate night out to the opera or seeing my son shine in the school play, the go-to outfit here for me is a special occasion dress like a graceful Ponté number, with a chic, three-pleat neckline that looks great with a statement necklace. You can dress this look up even more with a pair of heels, plus a cashmere cardigan if you tend to get cold in theatres (or, you know, school auditoriums).

What to Wear to a Concert

It had been a long time since I’d been to a good rock concert. The way they were shredding up there was absolutely mind-blowing. For a moment, I was thinking: is Van Halen back together, or is my daughter’s string section just taking this set to the next level? I really let my imagination wander as they ripped through “Twinkle, Twinkle Little Star.” After the standing ovation (no encore?) I ran over to my daughter and told her: “Yo-Yo Ma is proud of you honey.” She did not find this funny.

As much as I love going to the orchestra nights at school, I was inspired to buy actual tickets to a concert. For this one, I’ll be trading in my cashmere turtleneck and wide-leg dress pants for a trendy pair of straight leg jeans and my favorite band t-shirt.

What to Wear on a Dinner Date

As you can probably guess by now, my partner and I tend to have lots of meals involving mac and cheese, perhaps the kind with fun shapes on special occasions. While we absolutely love our family dinnertime, we also relish an opportunity to call the babysitter and hit the town. While, fine, not necessarily hit the town, but at least head into town for a nice dinner at that new fancy Italian restaurant.

For nights when we're swapping out the mac and cheese for handmade gnocchi and a candlelit restaurant, I love wearing a print fit and flare dress with booties. Throw some delicate drop earrings into the mix and voila! You've got an outfit that's comfortable enough to really enjoy the gnocchi in but fancy enough to fit the vibe of the restaurant.

What to Wear to go Out to a Club

My best girlfriend had been bugging me to get out of the house with her. I finally caved and we made plans for a girls’ night out at one of our favorite spots. Now, I’m no longer a twenty-something who spends nights out dancing in a club, but I still enjoy dressing up and going out with my girlfriends from time to time.

The trick is to make sure you’ve dressed appropriately for the kind of venue you're going to. We were hitting up open mic night, so I kept it a little more casual. I once again pulled out my favorite pair of straight-leg jeans because while I may not be a twenty-something, I still want my denim to be on-trend. I wore these with Chelsea boots and topped the whole look with a silky crepe women's blouse. I felt fabulous and comfortable enough to dance the night away when the main act hit the stage.

What to Wear to a Dinner Party

Somewhere on the spectrum between the family mac and cheese nights and the fancy dinner date lies the dinner party. We had one coming up at a close friend's house, so once we decided on a bottle of wine to bring, we got ready to make our entrance.

The key to getting ready for a dinner party with friends is to look dressy enough for the occasion while still feeling comfortable since, after all, a dinner party tends to include lots of delicious food, lots of laughs, and if you partake, a glass of wine or two. When you look and feel great, you can focus on the task at hand, which is enjoying the event. So, I chose to wear a flattering yet oh-so-easy crewneck sweater dress with a statement necklace, tights, and ballet flats.