Hello Jordan! Darling girl, I know exactly what you are talking about. Most guys seem to latch onto a particular "look" and feel that it can carry them on into middle age and beyond. (This accounts for the myriad Birkenstock and chino clad guys wandering the streets of the Bay area.) It's always a tough topic to broach, especially without offending said fashion-challenged beau. It takes delicacy, diplomacy and timing. I would suggest a weekend of pizza, action movies and/or football and then and only then a very casual, "Oh, by the way, here's a little something I picked up at the mall yesterday - 40% off!" (Money off is always a bonus in a guy's eyes!) Here are a few very appropriate and non-scary denim choices for your guy:
These standard fit, straight leg, classic rise jeans by Lucky are great. As are these BKE Alec jeans. Button fly, slim fit, dark wash denim. Hollister has a great low rise denim, the Boomer fit. Several different washes to choose from.