DONNI. The Pop Stripe Shirt

The wide-leg cut is actually wide enough to sleep comfortably in any position without the fabric twisting around your legs. The modal feels silky but not slippery, so they stay put through the night.

This is the bag that makes you look like you have your life together, even when you absolutely don't. The size hits that sweet spot where it holds everything you actually need without looking like you're carrying your entire apartment. I've watched friends carry theirs for years and they still look brand new, which justifies the investment.