DS (4) has sensory issues and clothing can be a big issue for him. I say this as he spins across the room in a cat-costume leotard and tutu and throws himself gleefully over the end of the couch into a headstand. Over and over again. *lol*
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I've found that the two big seasonal shifts -- moving into winter and moving into summer -- we always see a swing of heightened clothing issues. He just doesn't do well with the transition. It generally lasts a couple of months and then he mostly settles back into his usual pattern with clothing and sensory issues, which is still present but much less marked. As he gets older, we're still figuring out how to smooth the transition a bit, but there are a few things that have made it easier for all of us.
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-Unless he's at serious risk for frostbite or heat exhaustion, I don't worry too much about his clothing choices, whether or not they're "weather appropriate." Likewise, as long as his privates are covered, I don't worry about gender, color combinations, etc. The only hill I've chosen to die on is wearing socks, because his feet seriously stink when he wears just shoes or boots. Luckily, as long as he also gets to put socks on his hands, he'll put socks on his feet most days.
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-I experimented with him choosing his own clothes at the store and he just can't predict what's actually going to feel good against his skin after it's washed, when he's wearing it for hours, etc. So now I choose the clothing we get for him, and he chooses his own outfits from his closet. When he feels overwhelmed, we've worked to give him words and a routine for asking someone else to choose his outfit for him. I buy a range of clothing for him, from soft to textured, because his sensory needs change from day to day. Sometimes seams actually feel good to him. Other days, they make him scream.
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-As long as they cover his privates, our bin of dress-up clothes is fair game.
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-When he locks up and gets too frustrated to pick out clothes but won't accept anything anyone else chooses for him, and we need to get out the door on time, doing something like setting a timer for him just puts pressure on the keg of explosives. Not good. Instead, I'll grab an outfit or two and toss them in a bag and send him out to the car in his pajamas. He may or may not wear the pajamas for the rest of the day, but we have an option for him when he settles himself into his skin better. That usually happens by noon. (As he gets older, we're planning to transition him away from "Mama packing an extra outfit" to either him being able to settle himself before we leave or him packing his own bag.)
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-Sometimes heavy work or the Wilbarger brushing protocol can help get him to where he can stand to pick and wear clothes. I might ask him to push the back of the rocking chair to rock me while I'm sitting in it, or push a full basket of laundry to the washing machine, or carry the tumbling mat to the living room and do some tumbles, then carry it back again. As far as brushing goes, the brush our OT gave us to use with him is exactly the same as the corn desilking brush I got at the grocery store for $2. It's just a different color. In fact, I have a couple extra brushes around here that we haven't used yet. PM me.