The latest trend of rolling up jeans and pants is, to be honest, really cool. It’s practical (for bikers) and changes up the silhouette of typical pants. As an added bonus, it exposes some sexy ankle and transferrable to women’s fashions—and not just wearing men’s clothing, but pushing the fifties cropped-pant look. With that in mind, I must say I ship it entirely. Here are some examples of what some dudes are pulling off with their dress pants.

Outfit 1
First, I have to say, this outfit is so cute and dapper. He’s got this adorable, naïve dandy look going and it really works (just ignore the bag—to clear any confusion, purses are still a woman’s accessory). Rolling the pants up—black’s always a good choice—works wonders in two ways. First, it draws attention to his really amazing shoes. And, second, disrupts the whole breakfast-at-the-country-club look to make it new and exciting and ‘alternative,’ if you will.

Outfit 2
This guy has this weird librarian, history teacher look going for him and much like the first outfit, if it wasn’t for the rolled slacks, he’d look like a donation bin at Value Village. For the most part, his clothes are entirely unstructured, but the rolled slacks add just a dash of structure and mock-tailoring. That, and his hair cut. Baggy clothes are great and create wonderful silhouettes but there has to be something holding the outfit together so you don’t look too sloppy.

Ladies Touch by Maggie M; a freelance writer and fashion consultant.