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Style Debate: Rolling up your pants or jeans

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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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Worth the roll? Via GQ

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.

J.Crew at ShopStyle

Comments

  1. I don’t know if we’re talking about the same stuff, but I do cuff my pants in a roll. Not the kind in the first picture but those of Street Etiquette kind.

    I think it’s fine. Showing a lil ankle is the sexy thing now.

  2. I live in London but haven’t noticed this phenomenon anywhere than on style blogs! I shall have to look out for it more…

  3. I roll them, but not much. Same idea as having a quarter inch of your cuff showing under your jacket. I’ve seen way too many 3-5 inch rolls though and… come on man, the flood’s over.

  5. I understand cuffing/rolling for function, I wonder if the question should be extended to what kind of pants would you not cuff even if it is too long (meaning send them straight to the tailors)?

  8. I have to agree with many of the above sentiments. I never have rolled, (unless I need to… beach etc) and don’t intend to start. I wear pants so my ankles stay warm! And if it’s summer, then either wear lighter-weight pants, or shorts.

    But it’s not even about that. It’s just too intentionally disheveled, exactly like you say, Joe. I personally can’t get behind that.

    Just my view.

    Cheers,
    Ben

  9. Well, my inseam is technically something like 29 1/4″ so unless I want to walk on my pants, or spend tons of money on tailoring every pair of pants, I roll almost everything I wear. Either a simple cuff or a messy roll.

  10. No. Just no. I never saw this until it broke out on JCrew like an epidemic. It looks dumb. Worst of all, I can’t get a good idea of how their pant cuff will fall realistically on the shoe because all of their pics have their pants rolled up.

  12. I have a 33″ inseam, which is pretty difficult (impossible?) to find in a store. I have a short roll at the bottom of my jeans because otherwise they are too long.

  14. I’ve seen the rolled up look a lot in Manhattan during the spring summer time.

    I think it looks nice, but must match with the outfit/theme you’re pursuing. On my raw denims I prefer the tight rolled up look, but on canvas pants (or non-denim) I prefer the more disheveled look. Of course i don’t wear all my pants like this either.

  15. I’ve tried the “messy roll” before, but I always feel like I’m forcing things, so it never sees the light of day. I do cuff a couple of pairs of my jeans, though – just a single flip to keep them from dragging the ground or having too much break. Plus, the cuff adds a nice little bit of contrast between pants and shoes…kinda the same way a belt does between pants and shirt.

  16. Depends on the pants. The rolls you see in magazines are supported with wires sewn into the garment, so nothing like that. But there are practical reasons for rolling up the pant.

    If the pants are too long, they can be tailored or you can roll it. This only works on casual pants though. I have a few pairs of pants that I wouldn’t roll on flat shoes, but with boots I would roll them.

    It’s not about looking messy if you are doing it right. It’s actually to give a better break in the pant, and it also adds a bit of weight for a better drape. With some lightweight chinos, for instance, it keeps the pant from flapping while you walk.

  17. I usually try to roll because of how much I see it around. I think especially a lot of shoe ads do it to show off the whole shoe, but in GQ and Esquire you see it regularly promoted so I can understand why people try it so much. I think like anything, when EVERYONE starts doing it, it starts to get a little taboo. I haven’t been able to mimic the roll I see in the J.Crew catalog or any magazine I read, but I agree with a few people above me that really, if you have to roll, then roll, and if it looks better cuffed, then cuff, but don’t cuff just because you think it’s trendy. That’s exactly what will make it fade out.

  18. I do it now and I did it in the 80s. I like the look and hate my pants breaking when they touch my shoes.

  19. Done it a lot lately…only due to the amount of snow we got here in Chicago the last couple weeks. Now that it’s melting, I’ll have no need to roll ’em.

  20. Only when I’m wearing jeans I haven’t had the chance to hem, and I’m walking through puddles or snow. Otherwise I think it looks pretentious and juvenile.

  21. If I’m riding a bike, definitely. Also on a hot day it gives nice breeze and looks pretty good with some chinos or linen pants. But if its done on a day-to-day basis and only for style I feel like you have to smoke American Spirits outside of a trendy coffee shop all day.

  22. Agree with a lot of the above comments. I think age has something to do with it. I think it would be pretty hard for a 30 yr old man to feel comfortable rolling their pants if you dont have to. ( beach, pant too long, etc..) However, if you’re in the early 20’s, in college, no major responsibilities, then is much easier to pull it off. I think is one of those things that you leave for the younger crowd. On the contrary, if is extremely hot outside, it does promote a sense of casualness to your look. Personally, If i’m wearing chinos on my days off, I do a slight roll. But only in the summer/spring. PS. I’m 5’8, so the roll helps me appear a bit taller 🙂

  23. I won’t roll like the picture at the top, maybe a cuff like the second picture. It depends on the shoes. I like a 1ish inch cuff with my moc lug Red Wings. Why not shoe off a little more shoe when they look that good? Also, I think, much like wearing a scarf, too meticulous and too sloppy both look bad.

  24. I often roll my jeans and chinos once the weather starts to warm up. I have never rolled or cuffed my trousers or suit pants though. however I use no break wit all of my suits so a roll is not needed. I think it is a very “prep” thing to do. take.a look at any preppy designer from ralph lauren to j crew and u will find a cuffed pant. I personally like it and have always cuffed my jeans at least one roll. thought it looked better.

  25. Messy roll is just messy, unless I’m on the beach, but I’m on the fence with the tight roll. If your pants aren’t SLIM, they’ll flap around if they don’t have a break. But if they’re slim cut, a tight roll can look okay – just a bit dandyish.

  26. I couldn’t care less if every last guy walking around had a rolled cuff in their jeans….I would still be the only one not following this ridiculous trend!

  28. Interesting that some people think a man has to be either in his 20s or a douchebag to roll the bottom of their jeans.

    I’m 54, don’t ever drink Goose out of the bottle in a VIP room, have no soul patch or blown out hair and my skin isn’t orange. None the less I like to roll up my jeans to show off my boots. Wierd.

  30. IF you are short, like me, you don’t have many other options without having to cough up some extra dough for a tailor – and the good ones come at cost. There aren’t very many inseams that go to 28-29″…

  31. I’ve got the same problem. I’ve settled for buying black jeans on the short side and not rolling and blue jeans on the long side and rolling. My rolls are always crisp though.

  32. I don’t mind a little roll with my chukka boots, otherwise I think they look a bit like suede bowling shoes.

    I’m just trying to figure out if thats bare ankle showing or a flesh colored sock? Am I the only one who thinks that roll and ankle look strange?

  33. When I was in Moscow this summer, I saw a *lot* of people do it. Personally, I’m not a fan of it outside of practical reasons (riding a bicycle, pants too long, etc).

  37. I’m 39 yrs old, although look younger, and I roll my jeans and khakis which are generally of the slim variety. I work in a casual office environment and with my jeans or khakis usually wear chukkas, canvas shoes, or desert boots and the rolled up pant look looks pretty darn good in my opinion. The roll I do is not perfect but not messy either.

  38. Hey Vaughn!

    I noticed you said you’re from Charlotte. I recently moved to Charlotte and I am trying to find a good tailor and cobbler. Do you (or anyone) have any recommendations? I am new to the world of Style and advice forums such as Dappered too and I’m trying to build some resources. So far, great stuff!

  39. I have been taking the Northern Line down to Bank each morning in the 9 o’clock hour, and without fail, there are a few in each train (not counting the hipster-doufus contingent that gets out at Camden).

  40. Hiya Daniel –

    I am still on the outlook for a good cobbler – I just purchased a cool pair of Solovairs here in London that are going to need a gentle stretch. I have been told that the cobbler in the Arboretum (South Charlotte) is quite good.

    As for my tailor, I go to Piper Glenn Tailors – near the Trader Joe’s off of Rea Rd, just north of 485. They do damn fine work – although the language barrier concerned me at first, I won’t go anywhere else now.

    Hope this helps, and welcome to the Queen City!

  41. Thanks for the quick reply! I’ll be sure to check them out since I’ll be ordering an Indochino suit or two in the near future.

  42. It can be a nice stylish touch depending on the rest of the outfit. BUT…. look at The Sartorialist, another blog. This guy drools over the highest high water pants you ever saw. Like, the hem, or rolled cuff, three inches above the shoes. Ugly ugly

  44. I agree, a little ankle showing in the summer time is cool. I also enjoy cuffing my pant with camp socks. I got that idea via Street Etiquette blog.. Cool blog for those who dont know.

  46. I know my size and buy accordingly. So with the exception of a pair of Levi’s jeans there isn’t anything for me to roll. It’s not a look I find attractive and one I’ve yet to see in the UK. I don’t think we’re preppy enough yet.

  47. Some of u need to stop it! I roll two of the 11 pair of jeans I own so I don’t wall on them n look like a bum. I buy Jordans n sometimes LOUIE Vuitton shoes.. so y wear ragged up jeans. One role fine, its called needed style.. its stlye that has a reason.. rolling up to show ur legs.. wear shorts, that’s what there made for. DOUG
    MUSKEGON MI

  48. Dark jeans with selvage like the picture can handle a roll, but otherwise you probably shouldn’t.

  49. Most of those guys either looked like douche-nozzles already, or rolled their pants in such a way that it looked extremely messy.

    Also, rolling one’s pants is supposed to be functional, in one way or another; for instance, if you are wearing attractive, high-top shoes or boots, then one might roll his pant legs up to reveal the shoes, and this can look good.

    The men in these pictures were rolling their pant legs up while wearing low-tops with ankle-socks. ARGH! Awful!

  50. I am younger, but am in a similar situation, insofar as I am not rich or boring enough to drink expensive liquor while sitting in a VIP room, but I roll up my pants (a bit) to reveal my shoes. (High tops with visible socks.)

  52. I do not know how humble an opinion that uses the word “douchebag” can possibly be.