Tamaki Suoh- Pj shirt. They were not only big on you but they were super comfy so you would wear them anytime you stayed over. He never minded of course; he thought you looked cute in his shits.
Kyoya Ootori- His glasses. You only did this as a joke whenever you stayed over and got ready for school the next morning. Kyoya didn't really like it because not only did he hate waking up in the morning, he didn't like getting messed with but he would admit you looked cute in his glasses so he never really complained.
Kaoru Hitachiin- His shirts. He had some pretty nice, comfortable shirts that you would often wear because why not? Kaoru never minded though because he always thought you looked cute and stylish in them.
Hikaru Hitachiin- His jackets. His jackets were super nice and warm. Whenever it was freezing and your jacket wasn't warm enough you'd ask Hikaru for is. Of course him being his tsundere self would be stubborn and ask why but after you pleaded and begged, he finally gave you his jacket which made you smile as you put it on and hugged yourself for warmth then snuggled against Hikaru who rolled his eyes but wrapped his arms around your shoulders.
Takashi Morinozuka- Sweaters. They were soft and comfortable...not to mention literally ginormous on you because of how tall he is compared to you. Whenever it was really cold, you'd ask Mori if you could borrow one of his sweaters which made him nod as he got you one. When you put it on, it was literally down to below your knees which made you blush and giggle and Mori blush as well because he loved seeing you in his clothes.
Mitsukuni Haninozuka- Usa-Chan (Technically you both share it) He never really shared Usa-Chan with people. But he loved sharing it with you because he loved how cute you looked with it, especially when you fell asleep with it.
Ritsu Kasanoda- His School suit. You always put it on as a joke because he was much more taller than you so his suit was big on you obviously but you just liked trying it on for fun and it always made Ritsu laugh.
Yasuchika Haninozuka- Karate equipment. You weren't an expert at karate but you like to try and practice and most times Chika would teach you so he'd let you borrow the equipment from time to time.
Umehito Nekozawa- His cloak or Beelzenef. His cloak was surprisingly super comfortable and you'd get cold a lot so whenever he didn't have it on you'd always wear it and usually you'd be holding Beelzenef as well. He didn't mind it of course because he thought you looked beautiful in it and he was the only one who allowed you to do both.
(Enjoy. I'm only posting the ones I have preferences for. That's why they kinda seem scattered but enjoy for now!)