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Pants and Jeans

Should You Roll Up Your Jeans and Khakis?


man in blazer and rolled up pants

Last night I returned from my first mini-summer vacation this year. I went to a nearby resort to enjoy the wonderful thermal waters there and get some tan. After the first day, when we were all getting ready to go home because our skin just couldn’t bear anymore sun, I finally did it:

… I rolled up my khakis!

I’ve never done this before but, seeing other guys doing it, I just had to give it a try.

Picture this: a black and white striped polo shirt, a pair of khakis from Zara and a pair of blue and white boat shoes. I was a sailor all right.

If right before “the big roll up”, I was just a well dressed guy, AFTER the roll-up I was a well dressed rebel. I actually had to put on my new Pull&Bear glasses because even guys started looking at me.

I didn’t take any pictures unfortunately but here’s the effect of rolling up your khakis:

guy in blue shirt and rolled up khakis

He looks a little like Tom Sawyer, right? You should have seen me – I was a true sailor cruising around half-naked women starting at me. 🙂

According to The New York Times, this rolled-up pants trend first appeared in 2009 when a select few were doing it. In 2010 it became extremely popular and it seems that its popularity is growing hear by year.

The good news is that this isn’t something that will go out of style soon. The rolled-up pants look is daring yet it doesn’t cross certain boundaries.

Best part: you can roll up your jeans as well, not just your khakis. Take a look:

rolled up guy in jeans

All-in-all, this is a great look for you to try this summer. Remember not to wear any long socks when you roll up your pants. Low cut socks and no-show socks are best.

George Lavas

George is dedicated to fashion and style for men. Based between the UK & US he enjoys writing about lifestyle and fashion from both sides of the pond. George created BeStylish.org to help readers create a strong sense of style with minimum effort believing that everyone can look and feel good, all day, every day.

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  1. Joel May 19, 2011

    i actually tried rolling my jeans up… It felt a little odd being a 5’7 with an athletic body. I think this style looks great on thinner and taller people.

  2. JT June 3, 2011

    I can see it working in situations like the beach, running errands, something casual…in the club, never.

    Not for me. Wouldn’t recommend it either. But trying it? Please do.

    1. George June 3, 2011

      I was expecting a little more style courage from someone who has a dating site. 🙂 After all, a pair of rolled up pants is way cooler compared to a magician’s hat and goggles.


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