Don’t know about the skinny jeans part as our 14 year old son is usually in some athletic or lounge wear. That said, he is very active and hasn’t had issues with Dexcom or Omnipod for sports. He has worn his Dexcom on his upper buttocks and also the back of his arms. During basketball, he has used Diabands, available on Etsy, to keep the sensor protected and secured. They are essentially Lycra fabric bands that you can slip over your arm and they act as a tight sleeve over the site. Hope this helps, good luck!