This is probably the largest sz 27 I've ever come across from JBrand. I'm always 27 in JBrand (midrise, skinny, leggings, 10", Twill) and they always fit me TTS but this is definitely one size big. I could insert at least 2 fingers into the waist band as it's quite stretchy! It's also fairly roomy at the thigh though I expected it to be more snug for a fitted boyfriend. The smaller size is sold out and I am contemplating if I want to keep this and wear it slouchy.