My mother would roll in her grave to know it’s all coming back again. To accomplish the 2009 version of rolling up the cuff, simply take a pair of jeans, roll the cuff, but make sure it’s little loose on the bottom. You don’t want to do this with matchstick denim. Have fun with the style, but don’t look like you put on your guy’s jeans. Don’t pinch the jean either. Get a loose but slimming pair of jeans.

Victoria Secret took their Low Boyfriend Jean, it’s wide leg, rolled them at the cuffs and took a beautiful picture of a model in it. But in real life, the cuffs would be too big or require a pinch in them. If you look at both pictures of the link provided, the jean is form fitting at the waist even though it’s low and so it wouldn’t look right. Now look at Joe’s Jeans Cropped Ex-Lover. This is a loose fit jean but more slim in the leg. The cuff is a little more refined making it ladylike. Another great example is J.Crew’s Vintage Slim Jean.

The boyfriend denim can be accomplished with a pair of jeans already in your closet. With the boyfriend, a loose fit is best because it’s more casual – even if you pair it with heels.