Style Debate: Rolling up your pants or jeans

From the mailbag:  What’s with all the pant leg rolling?

Above:  J. Crew Broken in Chino, Relaxed fit – $59.50

I’m in the U.K. on Business, and I have a question on something that I’ve noticed a lot of here in London – men rolling (and in some cases peg-rolling) the bottoms of their trousers.  It seems like an epidemic here.

To be honest, I am from Charlotte, and we aren’t the most fashion-forward city, but I I can’t recall seeing this to be in vogue in other cities I’ve visited lately in the States.  In fact, the only place I recall seeing it in such abundance is in the J Crew catalogs.  What is your opinion?

– Vaughn

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Here’s my personal short answer:  I don’t get it.

Denim Heads will roll to show off their selvage if they’ve got it, and sometimes I’ll flip up the cuff on my non selvage jeans if they’re an old pair that’s a little too long and I don’t want to walk down the backs.  But when it comes to mimicking the J. Crew look, it seems like it’s less about the roll and more about the mess.

These types seem to be suffering from serious cases of I.D. – Intentional Disheveledness.  The above the belt version is pre-ripped and frayed baseball caps.  This below the belt version, although favored by those who dress a little nicer, is still of the same philosophy.  You just can’t force these types of things.  Because when you do (as seen in the pic at the top) you don’t look relaxed.  You look like you’ve been recently concussed and are seeing eight pant legs instead of two.

It’s no big deal either way, but as is often the case… if you have a reason to roll (walk on the beach, pants are a little long for your shoes, going as Huck Finn for Halloween) then by all means.

Your turn:  Do you roll?  And if so, tight or sloppy?  Leave it in the comments section below.