Landon, Help! Can A Shortie Wear Boyfriend Jeans?

Jackie writes: "Help! How do I wear boyfriend jeans as a shortie? I feel like I can never get the hem right and when I try to cuff them, they just end up looking really bulky and fall out. Is it just a dream?" I've been waiting for this one. Boyfriend jeans are tricky, and rest assured that even as a boy who currently doesn't have a boyfriend's jeans to wear, I've struggled with this pant style since the term came about. For example, I've always found the word a bit discomforting (in more ways than one): What about those of us who don't have a boyfriend's jeans to steal? Are we supposed to think buying the "baggy, pre-distressed" version of our skinnies is going to make up for its price tag that we could have otherwise avoided had we been in said relationship?  And why isn't there a Single Gal jean, hmm? All that aside, they're cute pants, and I personally live in them. A boyfriend jean, kind of like any relationship — boyfriend or otherwise — requires work. You've got to be willing to find the right one for you. I assume the idea of grabbing your boyfriend's jeans when you can't find your own (which, if you spend as much money on denim as I do, is absurd since I never let mine out of my sight) means that boyfriend jeans are supposed to look haphazard and like they fit someone else a little better. But, as with every other style of denim — skinny, cropped, high-waisted, mom-like — such is not the case. When buying your perfect boyfriend jean, you should get the waist right and worry about the hem later. The crotch drop should be relaxed enough that it gives off a feminine leisurely vibe — something your boyfriend's actual jeans won't be able to accomplish — and the fabric should have just the right amount of distress that relays a carefree, IDGAF attitude. As for the hem: Don't be afraid to take them to a tailor and tell them to cut off just the right amount of fabric that still allows for a messy, secure cuff at the bottom so that they don't add a second pair of ankles to your calves (click here for our tutorial on how to do it just right). These jeans from Gap will do the trick. Lastly, let's get rid of the "boyfriend" part of this trend and just call it for what it is: baggy jeans, mmkay?