An area we rarely talk about in menswear is how we wear clothes, rather than which ones we choose. Buttoning shirts, wearing collars up, belting trench coats and so on.

I know, it’s classic overthinking. No one needs to be told how to roll their sleeves, just like they don’t need to be told which shoe to put on first. 

But I do think some people would benefit from raising the topic. I regularly see guys that are into smarter clothing looking stiff because they’re not thinking about things like this. Or people in offices wearing their normal dress shirts with jeans, and keeping the sleeves buttoned. OK the shirt is the main problem, but it would look so much more relaxed if they folded them back.

It’s also easy to think these things should come naturally, rather than be taught. But I know the reason I roll my sleeves back is my Dad did it, and he could easily have done something different, or nothing at all. It’s worth pointing out the effect. 

Just thank your lucky stars we haven’t done a step-by-step video showing how to roll your sleeves, like some websites.

Rolling back your sleeves usually makes you look more relaxed, which with smart clothing can be helpful. It does so because it implies some kind of activity, where you would want your cuffs out of the way. 

The standard is folding the cuff back twice, so the sleeve ends mid-forearm. One fold is a little flappy, less practical, sometimes a little foppish, but it can also be more expressive (eg Adret, above).

More folds, above the elbow, suggest the labourer and physical work, and is usually less elegant. Picture Popeye. Fred Astaire used to do it (also above) but then he always looked as if he was about to jump off the walls and twirl round the light fitting. This was very active clothing. 

There is a third method where the cuff is folded back and pulled up, and the excess material below folded on itself. But this always looks too fussy to me.  

Is rolling sleeves physically flattering? I’m not sure. You’re basically cutting off the sleeve a to a three-quarters length, so the arm is shorter and no bigger. The advantage is really that sense of ease, the lack of constraint. 

Of course, you only do it with your jacket or sweater off, and it’s less easy with double cuffs. But those are rarer these days.

It does make obvious sense in summer, when there’s an advantage to having air running across the veins of the wrist. And that’s probably why I seem to keep my summer overshirts rolled up in the same way as a shirt (above). Unless they too have a shirt underneath. 

Although it’s something I also do with winter overshirts, flannels and the like, unless it’s particularly cold.

On the subject of chores – and similarly simple, casual jackets – a single turn-back of the cuff can be nice, especially if you need it because the arms are too long. It’s something I do with my Connolly suede jacket (above): I like the shirt-like effect, but it also helps get the right length. Squarzi, above, also does it well. 

One look I have tried in the past, and never seemed to work, is folding back the cuff of a shirt and an overshirt, so the shirt cuff is on the outside. Or doing so with a jacket, so the shirt sleeve comes out of the bottom and is folded back on top. 

It always seemed too showy, even if practical (when wearing a shirt and an overshirt in the summer, for example). The image below shows an exaggerated example, and it’s an outfit that has many other things wrong with it, but the shirt sleeve over the jacket is definitely one of them. 

What else? 

Pushing back the sleeves of knitwear has the same relaxed effect (below), but can stretch a sweater, making the sleeve wider and shorter. Washing or steaming will often fix this, but you don’t want to be doing that every time. Best to either always have that length or keep it for  denser knits.

Leaving shirt cuffs undone and letting them hang (with or without jacket) can have a similarly relaxed appeal, but doesn’t work if your sleeves are actually the right length. (I’ve been forced into it recently with old shirts, where the sleeves have become too short.)

Overall I think it’s worth raising these kinds of ‘how to wear’ topics, pointing out why they can appeal, and then leaving people to play with it. Play is how we learn, more than dictat or instruction. 

There are other pieces in this area in the ‘Rules’ series, where we discuss various rules or conventions with the aim of understanding rather than following blindly. They include buttoning a jacket or not, and keeping a DB buttoned or not. 

Let me know if any other ‘how to wear’ topics would be interesting.