Q and Answer: Can I roll up khakis?

Alex asks: Should I roll up my too long khakis or is that for jeans only?

You can roll up khakis as long as they don’t have pleats. Take a look at this lady rocking her boyfriend’s chinos in the latest Lands’ End Canvas collection. I’m not saying that you can take all of your tips from the ladies, but this one is safe. Basically, you don’t want the top of the khakis to look too blousy—unless you’re going for a 90s AC Slater pegged-leg look. When you roll up the bottoms of your pants, it’s possible to create a triangle shape from the waist line to the ankle instead of the flattering rectangular shape that’s commonly seen in the drape of most men’s pants.

I’d recommend getting them permanently cuffed or hemmed—depending on what look you’re going for. And after the tailor gets you fixed up, don’t be afraid to roll them up when you’re out on the water catching crawfish or walking your lady along the beach.

(above: Not everyone can pull off that Panama hat but I think you’ll agree that Mr. Connery looks just fine with the khakis rolled.)

UPDATE: While browsing the Spring - Summer 2010 collection from Woolrich John, Rich & Bros, I noticed a couple of models with rolled khakis—take a look.