photo via ksubi

Ready to graduate beyond boyfriend jeans? They're only getting looser from here on out. Let me start by saying: This is not a trend for everyone. Oversized jeans look best on a willowy physique, and they should always be paired with heels to counter the sloppiness. I like them with both fitted and loose tops—but not too loose, or you'll look like you're drowning.

I thrifted a pair a couple weeks ago and affectionately call them my "mom jeans." They're pretty long, so I wear them cuffed above the ankle. It's a work in progress, but as a teen of the '90s, I've got a little experience with the baggy jeans look. Aaliyah, the queen of '90s hip-hop style (R.I.P.), was one of my first style icons.