Our Family Dinner Ritual

Nine-year-old Toby has never met a ritual he doesn’t love, so he came up with a great idea for the winter…

Our Family Dinner Ritual

He suggested that once a month, we all dress up and go to dinner. When he first suggested it, I figured he wanted to go to super fancy places, but he proposed the local Indian place and our neighborhood diner. This month, we went to Rucola, a low-key Italian spot. The boys ordered Shirley Temples, and they always love the bread basket. To make it feel extra special, we dressed up in holiday outfits from J.Crew.

Our Family Dinner Ritual

Toby has always been into the idea of suits. (For his fourth birthday, he asked for a blazer.) Here, he’s wearing the Ludlow suit jacket and pants, paired with this button-down. All of the pieces have a hint of stretch, for extra comfort. And he’s really into the velvet slippers, which are reserved for the fanciest of occasions. (These are also cute.)

Our Family Dinner Ritual

Meanwhile, when it comes to dressing up, Anton goes with the flow. He mostly wants comfy pants and sneakers. Anton wore his Fair Isle half-zip, which he has pulled on many times since. (He likes that it has dogs.)

I’ve spotted slip skirts on other women around town, and this burgundy one is such a nice winter color. I paired it with a V-neck sweater I’ve worn approximately one thousand times. I like that it looks equally good dressed up or down — I’ve even worn mine with joggers! And these suede heels are comfy enough to walk around in and pull everything together.

Our Family Dinner Ritual

When it comes to dress-up clothes, J.Crew always gets it right. The fit is great and the little details make every occasion feel special. (How pretty is this look?) Plus, they’re the kind of pieces that work perfectly for weddings, family parties, celebratory dinners, and all those special life moments.

Do you have any holiday rituals or traditions? I’d love to hear…

Bonus for all readers: J.Crew is offering Cup of Jo readers 15% off (stackable on top of other sales) using code CUPOFJO. (I have my eye on this.) Good through December 18th. Thank you so much!

(Photos by Christine Han for Cup of Jo. This post is sponsored by J.Crew, a brand our family has worn for years. Thank you for supporting the brands that help keep Cup of Jo running.)