When she walked in the restaurant she looked at my daughters and rolled her eyes “how did you get them to wear a dress?”. I sighed back at her. There had been some discussions and eye rolling. Getting kids of any age to dress for the occasion is not simple and for some parents it is a bitter battle. Here are four tips to move towards constant conversation instead of constant conflict, and get your child to dress appropriately in the end.
- Make sure your child has nice clothes that fit them and look good. Taste aside, if a dress doesn’t fit, or the pants are 2 inches too short, you are fighting a losing battle.
- Check to see if the clothes are actually comfortable. Shirts don’t have to be starchy, waist bands don’t have to be itchy. The fabrics now are amazing. Finding second hand clothes has been key for us because those are usually softer after so many spins through the wash.
- Let them accessorize and add their own style. We compromise with shoes a lot. Boots or sneakers with that dress – okay great. Denim jacket with velvet dress – fun. Mom’s big chunky earrings – don’t lose them! For our guys, they almost always wear trainers with their suits. But they look great and it gives them their own style.
- Go for the jacket. We almost always have a light weight white and a similarly a little black jacket (short sleeved or ¾ length) for the girls to wear over their strappy dresses to provide more coverage. They can feel like a supermodel at home, but throw on the jacket to keep it classy for mass or the dinner with grandma. For the guys, having a sport coat on hand can class up jeans and more casual shirts. Men’s jackets are also more forgiving as the boys grow. As long as it fits through the shoulders the sleeve length can be more forgiving- assuming the shift underneath fits.
Your child has so much to learn in life and learning how to dress appropriately is one of those things. One mom I know recently asked her daughter “how would you like it if I showed up to your softball game in a prom dress?”
It wouldn’t be appropriate.

And that should be the emphasis in the conversation. Don’t tell them they look lazy or sloppy or slutty. Don’t body shame. Simply explain to them that there is an unwritten dress code for certain events – not everyone knows of this so others may be dressed inappropriately. Someone showed up to my wedding in a t-shirt and jeans. I still remember what that guy was wearing 22 years later because it wasn’t appropriate.
We communicate to others the value of the event and the importance of the engagement, by dressing in line with the cultural expectations. We also communicate our awareness, affection, and appreciation to those we are with when we take time and care with our dress. It isn’t vanity. It is an outward expression of respect because how we look is also a reflection upon them.
My boys tried to out-dress one another this week when their grandmother took them to dinner. I simply said “dress nice”. My 17 year old said he had already asked Grammie if ties and jackets were required. They were optional, yet both boys wore both. As they were leaving, one of them said “Grammie is going to love this”. And she did.
For more on parenting tips you can check out the old blog or the podcast. Thanks for stopping by!