How to roll up your shirt sleeves - The definitive guide

Rolled up sleeves on your dress shirt gives off a cool and casual vibe, if done the correct way that is. By avoiding sloppy techniques that will risk leaving your dress shirt wrinkled, you can feel comfortable and stylish all day long. In this guide we’ll touch on how to do the roll up correctly, where and when it’s an appropriate style and other information that may be useful.

Some guidelines to begin with

There are some general guidelines to start off with before going more in-depth on the rolled up sleeves topic.

The sleeve length

Rule number one, and perhaps the most important one, is the sleeve length. The sleeves should leave several inches of the wrist visible, to avoid looking like you’re wearing a too big dress shirt that you just had to roll up.

Keep your elbows hidden

Second, the sleeves should not be rolled up high enough for the elbows to be showing. This could risk giving off a sloppy and thoughtless vibe to the overall outfit. Although, is it a practical necessity to roll up your shirt sleeves even higher then you should of course do so.

When should you roll up your shirt sleeves?

First off, let’s make it clear where and when rolled up shirt sleeves are an appropriate style. There’s a couple of occasions worth mentioning when answering this question. The most obvious occasions is, of course, when it’s a practical necessity. That means, rolling your sleeves when getting your hands dirty, when washing your hands or helping out a friend with moving and where heavy lifting is involved is totally acceptable. Also, the weather is something to take into consideration in this topic. Facing some hot summer days ahead? Rolled up shirt sleeves lets you cool off when you need to, without feeling guilty of breaking any fashion rules. Rolled up shirt sleeves could also works as a temporary solution if the sleeves are too long. Remember though, this is only a temporary solution to a permanent problem. Getting your dress shirt in a tailored fit reduces any risks of getting a bad fit.

Is it a Business casual look?

Rolled up sleeves on a dress shirts typically works best for casual occasions and gives off a relaxed vibe. Looking to wear rolled up sleeves for work as part of a business casual look? Depending on where you work, it could be acceptable or a big no-no. If you work somewhere more informal and casual, rolled up shirt sleeves is often seen everywhere and totally acceptable. On the other hand if you’re working at a strictly formal company it might be a good idea to leave the sleeves on your wrists. To answer the question in short, rolled up sleeves can be business casual depending on where you work and what type of occasion.

Ways to roll up your shirt sleeves

There are some ways to make the process of rolling up your shirt sleeves easier while securing a stylish and casual look. Obviously there are a ton of different methods out there, but these two works great and are suitable for different occasions.

The Casual Forearm Roll: A casual and easy way to roll up your shirt sleeves while avoiding any wrinkles. Just unbutton the cuff on your dress shirt and flip it back as well as inside out. Next, fold it over once making the cuff hind behind fabric. To finish off the look, simply tuck in the corners of the cuff and you’re good to go.

The “Master” Sleeve Roll: Looking for a more stylish way to roll up your sleeves? Then this method is for you. Similar to the casual roll, start off with unbuttoning the cuff as well as any other buttons on the sleeve. Proceed to flip it back and inside out and pull the flipped cuff all the way up to just below your elbow, without folding it. Lastly, fold the bottom of the sleeve portion up until it traps the bottom of the cuff portion.

Methods for thicker fabrics: This method is great for dress shirts with thicker fabric, for example flannel shirts and chambray shirts. Start with your shirt sleeve fully extended and proceed fold the cuff backwards until it’s fully inside out. Then proceed to roll it upwards until you’ve reached your desired length. Remember to keep it below the elbow for a clean look.

Roll up without wrinkles

By improving your technique it will be easier to create neatly rolled up sleeves without any visible wrinkles to it. Another important aspect is, as always, making sure that your dress shirt is a perfect fit. An ill-fitting dress shirt with bad proportions will most likely also result in badly executed rolled up sleeves with a lot of wrinkles. Pressing or ironing your dress shirt before rolling up any sleeves will also help to get rid of any unwanted creases in the fabric.

Do’s and don’ts

We’ve already covered some aspects that will help you master the skills of a well executed roll up. How about things you should avoid when going for a rolled up casual look? For starters, skip the tie if you’re rolling up your sleeves. This is a general advice and you should, as always, stay true to your own taste and style. However, wearing a tie with rolled up sleeves is somewhat contradicting and makes formal clash with casual in a not so flattering way. Another thing you should avoid doing is leaving your sleeves folded while wearing a jacket over it.

The best way according to us

We like to think that although there is no supreme method when it comes to rolling up sleeves, some methods are definitely better than others. A casual forearm roll is a great method to start off with if you’re uncertain which method suits you the best. It’s incredibly easy to execute and will create a good result every time.