Lots of readers/viewers have been asking me to do an article and video about how to roll or cuff men’s pants, so I’m finally doing it! The article is great and all, but the act of rolling your pants is not something easily shown in still images, so do yourself a favor and watch the video below for the fully experience.
With the exception of jeans and boots, you should only be rolling your pants in the spring and summer, unless you’re in a climate where it’s warm all year-round. This is very much a warm weather flair to add to your dark wash jeans, chinos or khakis or even wool pants and trousers. But it is a little odd to wear during the colder, winter months.
How To Quickly Measure Cuff Width
Before we begin, let me show you a quick and dirty way to figure out the proper width of your cuff by using your finger joints. The each joint of your index finger is roughly an inch long.
So if you need the cuff width to be about 2″ wide, the top of the cuff would hit right around the second or middle joint, like in the picture below:
The Simple Cuff
This cuff works especially well with slim fit jeans. I like to use this cuff when I’m going for a cleaner, sleeker look with a client. I’d caution against using it with chinos or other pants, as the fabric can be a little floppy around the ankles.
You also want to avoid using this cuff if you’re wearing straight fit jeans because your ankles will be swimming in a bunch of fabric. Use the pinroll cuff in the next section, instead.
Before you start cuffing, you should already have your jeans and shoes on. Otherwise, it’s harder to tell what the finished product looks like and if you’re showing the right amount of ankle. Hopefully you’ve already seen my men’s jeans fit guide so you know that your slim fit jeans should have a slight break at the hem. This cuff won’t look right with any other type of pant break.
How to Cuff
Low Top Shoes
If you’re wearing low top shoes, roll up your jeans’ cuff once.
The cuff width should be between 1.5” to 2”. If you’re on the shorter side, get the cuff as close to 1.5″ as possible. If you’re on the taller side, go for 2″. This will maintain the proper promotions for your body type.
Make sure that the roll is the same width or thickness on the front and back of the pants before you do the second roll. After finishing the second roll, the bottom of the cuff should just hit the top of your outer or inner ankle bone, like in the image below:
Boots or High Top Shoes
It’s the same as low tops: do at least 2 rolls and make sure to maintain the 1.5″ to 2″ cuff width, depending on your height.
The bottom of the cuff should either lightly graze the top of the shoe or boot or go a little bit past the top of the boot or high top. The image below, has the pants rolled up 3 times on the left and 2 times on the right. Both are equally acceptable lengths. I prefer 2 rolls, as 3 makes it look a little too military for my tastes, but 3 is just fine if that’s what you prefer.
The Pinroll Cuff
Again, start with your pants and shoes already on. Check my men’s jeans fit guide and chino pant fit guide for details about the type of break your pants should have before cuffing. If your pants aren’t fitting properly or they’re too long at the hem, the roll will look big and chunky around your ankle, which you don’t want.
How to Cuff
Low Top & High Top Shoes and Boots
With your thumb still holding the fold against your ankle, start rolling the cuff up with both hands. Make sure the roll is between 1 to 2 inches wide. If you’re on the shorter side, keep it around 1″ and go closer to 2″ wide if you’re taller. This will maintain the proper proportions for your stature.
if you’re wearing low tops, you want the bottom of the cuff to hit around 1.5 to 2” above your outer ankle bone, like the image below. If you need to roll 3 times to get there, do that.
The only exception to the 3 roll maximum is if you’re wearing boots or high tops. Then you need the cuff to just cover the top of your boot or lightly graze the top of your high tops when standing up. The image below has the cuffs rolled twice.
That’s it! Now cuff all the things!
I’ll just cut right to the chase – there’s really only 2 good ways for how to roll up sleeves. Do one of these and never think about it ever again.
A quick note:
The images for how to roll up your sleeves below are from Esquire, whom I love and work with, but they’re rolling their shirt sleeves above the elbow. You should NEVER do this, because, while it looks great in pictures, it usually looks like the image to the left in person – lumpy and just, not good. It will never look as good as the pictures, I promise you.
The Basic Roll
- Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
- Flip the cuff over. Your cuff will dictate the width of your roll. If you have a stiff cuff, normally found on dress shirts, do not fold the cuff in half to make a slimmer roll. It will ruin that shirt’s cuff forever. If it’s not stiff, like with an Oxford button down dress shirt, then you can fold it in half for a less wide roll, although I wouldn’t advise doing a half roll. It usually looks better with the full cuff.
- Roll it again, and again, and one more time so that the top of the roll should stop just below the elbow, or mid to upper forearm (see the video for details).
- If you go above the elbow, the roll starts to get really bulky and it’s just not a good look. As a woman, I love when the shirt cuff hugs the muscular part of the forearm. It looks very… raaaaawwrrr!
The Italian Roll AKA The GQ Roll
- Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
- Fold the sleeve up, so the entire cuff is an inch or so above your elbow.
- Next, roll your sleeves up onto the cuff, using your thumb to sort of tuck in the shirt into the roll, but still allow a little bit of the cuff to be exposed at the top.
- The top of the roll should hit just below the elbow, by about half an inch. Then you hopefully have about an inch of shirt cuff exposed above the elbow.
I see a lot of articles and videos about all the possible ways of tying a scarf, but honestly they’re mostly useless, ugly or both! So these are the 4 best ways for how to tie scarves for men and how I tie scarfs on my clients for cold weather events or publications like GQ & Esquire. Throw out all the other ways to tie scarves, they’re a waste of time!
A quick, note about length, material and patterns
This and socks is one of the few places where you really can’t go wrong with any choice. So I always tell my clients to have at it and choose anything they think looks great, it’s a perfect way to show off your personality. So any colors, patterns, materials and lengths that you like, go for it! You can’t go wrong here.
Here’s the 4 best ways for a man to tie his scarf.
This way of wearing a scarf is perfect for those who don’t like anything wrapped around their neck but still want to keep warm. I like it because it’s easy to do and it looks nice. It doesn’t do too much to keep the front of your neck warm, but it does keep the back of your neck as well as the side of your coat nice and insulated.
Definitely wear this underneath your jacket or coat, it’ll keep it in place. Otherwise, it’ll move around a lot as you walk.
- Take the two ends of the scarf, have them hang equal length on either side of your neck.
- Now simply tuck in each side of the scarf under each lapel of your jacket or coat. It seals in the small gaps between your chest and coat to keep you nice and warm.
It’s a pretty standard way of wearing a scarf. You probably wore yours like this as a kid and it’s just fine for men. It’ll do what The Drape won’t do – keep the front of your neck warm.
- Start by putting the scarf behind your head and lowering one side to be twice as long as the other.
- Now wrap the longer side once around your head. The ends can be equally long or uneven. It doesn’t matter.
- Tuck the excess under your collar or lapel, if you want.
This is my absolute favorite way to tie a scarf on a man and the warmest way to tie a scarf. When I see men on the street wearing a scarf like this, I think it just looks so damn sharp! You can’t go wrong with this way of tying a scarf.
- Fold the scarf in half.
- Wrap it around the back of your neck.
- Tuck the loose ends through the loop created by the other side of the scarf.
- Adjust to desired tightness.
This way of tying a scarf tends to look best with longer scarves, but you can get away with it if you’re using a shorter one, too.
- Put the scarf around your neck, making both sides equal in length.
- Cross the two ends.
- Push one side up and under the other.
- Pull it tight (but not too tight—breathing is important even in winter!)
That’s it! Those are the best (and only) ways for a man to tie a scarf.
I was lucky enough to style the massive, in personality and stature, Keith Olbermann for a recent GQ spread. (My hands also make their modeling debut in the spread, as you can see in the above pic.)
Olbermann is (for lack of a better word) HUGE. When I was on set with him, and now seeing these pictures, I was reminded how important proportions are. If you’ve never seen him in person, you won’t understand just how big he is. Even the article touched upon it:
“Keith Olbermann is a large man. Conventional wisdom says TV adds ten pounds to people. Maybe. But conventional wisdom rarely applies to Olbermann. And seeing him in person, you realize TV makes the man appear smaller. In life—life outside the electronic box—he’s a good six feet three, with a chest that suggests a retired football player.”
The Importance of Proportions
When the magazine first sent me Keith’s sizes, I couldn’t believe it. Clearly these weren’t right. From all the pictures and videos I’d seen of him, I assumed he was average-sized. Upon confirmation that the measurements were accurate, I realized that Olbermann was a master of proportions.
Keith has consistently worn perfectly fitted suits for his stature. Couple that with appropriate-sized lapels, dress shirts with spread collars, and perfect tie widths and you’ll fool even a professional, like myself, into thinking you’re average-sized.
Example: The image below shows Eric Stonestreet (L) and Olbermann (R). Would you guess that they’re about the same size? I’ve met them both and they’re closer in size than you’d think.
This highlights exactly what I’m saying.
Eric is wearing a suit with regular width lapels and a skinny tie. Notice how he looks way larger than Keith?
To overcome Keith’s size, and what I would’ve done with Eric, I went with wide lapels, which have an amazing slimming effect on larger builds. One thing Eric did correctly was wear a dress shirt with a spread collar. Unfortunately, he should’ve chosen a wide tie (3.5″ at it’s widest point) and tied an equally substantial full Windsor knot to finish off his look, which is great for guys who are tall and/or have large torsos.
Golden Rules For Proportions
The width and knot of your tie should ALWAYS be in proportion with the lapels of your suit and the spread of your collar.
Here’s a quick breakdown for your height and build:
Tall & Slim: Regular width suit lapels, spread collar, 3″ wide tie, and half-windsor knot
Tall & Broad: Wide suit lapels, spread collar, 3.5″ tie, and full windsor knot
Average & Slim: Slim suit lapels, semi-spread collar, 2.5″ skinny tie, and half-windsor knot
Average & Broad: Wide suit lapels, spread collar, 3-3.5″ tie, and full windsor knot
Short & Slim: Slim suit lapels, semi-spread or point collar, 2.5″ skinny tie, and half-windsor knot
Short & Broad: Regular width suit lapels, spread collar, 3″ tie, and full windsor knot
Keith says: “Get your damn proportions in order!” (Not really. But that’s what I imagine him saying in this picture.)
Here’s a scenario: You’re getting dressed for an event. Your suit’s been dry cleaned, shoes have been shined, your new dress shirt is ironed and you’re all set to go. You put on your pants, tuck in and button your dress shirt, buckle your belt, tie your shoes and throw on your suit jacket while giving yourself a once-over in the mirror.
But something looks off.
There’s too much shirt sleeve peeking from underneath your jacket! Most (sloppy) guys will shrug it off and continue their night like it’s no big deal.
PLEASE don’t be like most guys!
There’s a quick and simple fix called “The Rubberband Trick”
1. Grab 2 rubberbands.
Make sure they’re large enough to wrap comfortably around your forearm without cutting off your circulation.
2. Remove your jacket, if it’s on. Place a rubberband over your sleeve, onto your forearm.
Around the middle of forearm, where there’s the most meat.
3. Tug your shirt sleeves up until your cuffs hit your wrist (this is the appropriate sleeve length).
Your cuffs should end at the bend of your wrist. Bend your wrist up and your shirt cuff should be barely touching the top of your hand.
4. Repeat for the other arm.
5. Throw on your jacket, adjust as needed and you’re ready to go!
Make sure that only about 1/2 of cuff is showing from underneath your jacket. If your jacket’s sleeves are short, adjust your shirt sleeves to only peek out a half inch. It’s better to have shorter sleeves with proper cuff spacing, than the opposite.
The rubberbands will hold your sleeves all night long. Just make sure, that if you remove your jacket at some point throughout the night, to take the rubberbands off your forearms. You’ll get some odd stares if you don’t.
Nick Wooster, master of sartorial style & Creative Director of J.C. Penney, clearly knows what he’s doing when mixing patterns.
The key to wearing patterns, especially bold ones like this herringbone jacket and harris tweed tie, is to break it up.
Without the solid black vest, his outfit would just look like one giant fabric swatch and frankly, like you’re trying too hard. The vest frames the tie, allowing it to complement the outfit, and helps break up the 2 different patterns. Look at how much cooler, almost relaxed the outfit looks with that vest. Adding the white cotton pocket square also helps.
Let me also mention the other details that really pull this all together:
- The collar of his shirt lays neatly under his vest – as it always should!
- Hair perfectly coiffed.
- Facial hair groomed impeccably.
- The thickness of his frames complements the jacket pattern.
Source: The Sartorialist