Under certain conditions I can appreciate this look on someone else, but I’m not a huge fan. Rolled up cuffs cut the leg line and so do pants cropped at an unflattering length. Before you know it, you’re sporting a leg shortening look, which isn’t as attractive as a more proportional or leg lengthening one. So please proceed with caution when you roll up or cuff long  pants and jeans.

Here are a few ways to lengthen the leg line and balance out the effect of the cuffs:

  1. Keep the hem width tapered: Rolled up wide widths seldom work because they are too horizontally cutting. Keeping the silhouette sleek reduces the horizontal integrity of the cuff and is infinitely more flattering.
  2. Keep the roll at the ankle or above the widest part of the calf: The post I wrote last year on boyfriend jeans illustrates this point. It’s the in-between length that can result in a dumpy silhouette.
  3. Choose a low contrast cuff colour: Dark stone washed jeans have high contrast cuffs whereas light stone washes and pants create low contrast cuffs. Low contrasts are less visually horizontal which in turn elongates the leg line.
  4. Choose a low contrast shoe colour: Keeping the shoe colour low contrast or close to the colour of your skin tone visually extends the length of the leg.
  5. Add a waist cinching belt: Creating a defined waist with a belt elongates the leg line above the crotch point thereby extending the leg even further.
  6. Add heels: Unless you have super long slim legs, it’s best to wear this look with a relatively high heel to balance out the effect of the horizontal cuff and the dangerous length of cropped pants.

In some cases you’ll apply all the guidelines at once whereas in others you will use only a few at a time. Personally, the only bottoms I feel good rolling up are clamdiggers, which end on the knee after they’ve been rolled. I find this length flop proof because a break at the knee doesn’t shorten the leg line. I can wear my flats and still feel fab. As for rolling up long pants, I’m passing on that look for now.

Are you cuffing and rolling long pants and jeans?

J. Crew MiH Jeans LondonThe Captain TrousersCotton Poplin Roll Hem PantsSlouchy Belted PantsFulton Slim Crop in True BlueHeritage Washed Silk Cargo Pant

These are rolled and cuffed pants/jeans and shoe combinations I find flattering. The lengths are more or less in the right place and the footwear is high-heeled (apart from one pair of oxfords) and low contrast against the foot.