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My middle child (seven years old) hates dressing up. Well... sort of. He likes shopping for dressy clothing (slacks, vest, button-down shirt, tie) and has a respectable collection. He'll even occasionally wear it around the house when playing pretend, or dress all his stuffed animals in ties. However, when we actually need to wear somewhat dressy clothing to something, he "hates" the clothing, "looks ugly" in it, is "uncomfortable", and expresses these opinions repeatedly and at loud volume while getting dressed. He also sometimes outright refuses, and ends up doing passive resistance (just lying on the floor) while a parent stuffs him into the appropriate clothing.

I think that his dislike is somewhat rooted in the type of event that we'll be going to: it often requires a level of quiet, still behavior that is a challenge for him anyway. The clothes end up being a convenient scapegoat. However, this is just one of those unavoidable parts of life: there will be weddings, funerals, anniversaries, and other parties where dressing up helps show respect for the occasion.

I tried for a while to be very enthusiastic about how nice and grown-up he looked, but it didn't really make much of a difference. (It might have made him even shyer, since he doesn't like being noticed, but it's hard to tell.) He already gets to choose whatever he wants to wear. Are there other strategies that I can try to try to make this less of a flash point?

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    Hmm... 7 years old. Have you tried... bribery?
    – user11394
    Commented Apr 25, 2015 at 16:19
  • Can you think of a single occasion where you saw a dressed up family with a kid wearing normal clothes they like and you were offended? Those who have kids understand. Those who don't probably aren't paying attention. If you want him to wear a suit, get an iron on patch of a ninja turtle and sew it on like an ivory league crest. Funny how a small thing like that can get them to flip on the subject.
    – Kai Qing
    Commented Apr 27, 2015 at 22:33
  • I would excuse the child from having to attend these events as much as possible. He could visit a friend or you could hire a babysitter. (I like to pick my battles.)
    – aparente001
    Commented Apr 28, 2015 at 7:15
  • I don't think letting him wear whatever he is comfortable in, or existing him from any event that requires some maturity and patience, is a particularly good preparation for being an adult. I am willing to give a primary school child some leeway (he chooses his clothes, he brings along a book to occupy himself), but not total control. I am looking for a solution that keeps him part of these events and teaches him the value of being presentable and appropriate to the occasion.
    – Acire
    Commented Apr 28, 2015 at 22:25

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My approach in a similar situation: There is an appropriate "costume" or dresscode for every occasion, not only for formal events. Shoveling snow? Business meeting? Scuba diving? Your wedding? None of them exactly a jeans-and-t-shirt day, right?

So make clear that every member of the family dresses appropriately for the day, depending on what's scheduled. Don't fuss, this is just matter of fact. If you praise clothing, compliment on everyday occasions as well: "That shirt looks good on you! That colour goes well with your eyes / hair / some accessoire!"

My children own three types of clothing:

  • "Good clothes" for festive occasions, but we take care that they get worn not only on very "strict & boring" occasions, but also on reasonably fun yet festive events. There is always a birthday, Easter, Christmas visit to the grandparents (where they will have nothing but fun and candy, sigh)... Input is appreciated, but Mom has final authority on what to wear. Hint: Choose wisely when shopping and whichever combination child chooses will be ok - leaving them feeling in control and parents sane.
  • "Town clothes" for school, shopping trips, doctors visits and other outings. We call them town clothes because where we live, the kids play a lot outside and usually wear clothes from the next category. This is where child gets to choose what to wear, but Mom keeps the right to veto if the choice is really, really too, aehm, eccentric.
  • "Outdoor or play clothes", which have the occasional stain, tear (mended) or other sign of wear. This are the clothes where Mom doesn't care if one climbs trees, mucks a stable or plays soccer in. This is where they have highest degree of freedom: A few days ago daughter decided to wear a bright orange dinosaur shirt with a pair of fuchsia jeans. I can still feel my retina peeling from the view, but so be it.

Now, this does not mean that you have to spend a lot of money. Especially in the first two categories there is some overlap: A good pair of pants can be dressed up with a dress shirt or dressed down with a t-shirt. A school jeans worn with a shirt and tie is good enough for all but the most formal occasions. A basic turtelneck is really versatile. Work with what you have. Accesoires help a lot to set the tone of an outfit and are quite cheap.

(The last category basically fills itself automatically in my experience...)

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    I would add praising the child for selecting the right type of clothing, and getting it on by themselves.
    – user11394
    Commented Apr 25, 2015 at 21:20

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