I use my iron just about every single day, including vacations. It's a skill that my mom taught me when I was very young and something everyone should know how to do. For some reason, about half the people I talk to don't know how to iron a shirt properly. So, with that said, this will be a quick tutorial on how to iron a dress shirt. What I will show also translates to short sleeve, polo shirts, and t-shirts with some slight modifications. Iron quality does matter so don't buy the cheapest one you can find. I will write a future blog on iron types because I am just about due to purchase another one. If your iron has tempature settings, I always suggest you error on the lower temperature option in each category.
I always start with the the cuff first because I have found that if you iron them last you tend to wrinkle the body of the shirt that you just ironed. Unbutton the cuff and sleeve place the button. Then, iron from the inside especially if there is a contrast fabric on the inside. Once you are done with the cuff, I button it back up and then lay the sleeve out flat. I always start from the the seam and move toward the outside (or top) of the sleeve to create the proper crease. I normally work my way from the arm pit area toward the cuff but I suppose you could go the other direction.
The collar and shoulders are next. If it is a button down collar, you need to unbutton and then lay flat. I don't spend much time on the collar, just a quick pass will do. I do the majority of my ironing work on the wide end of the ironing board, not the tapered end, because you have more surface area to work with. The tapered end I use more for smaller shirts, crew/v-neck shirts, and shorts because it is easier to position the clothing.
For the shoulders, use the 90 degree rounded corner section to position the shoulder of the shirt and then you can iron that area easily. This is how you get ride of the hanger creases and hanger nipples (that's my technical term).
The last part of the shirt I iron is the body. For some reason, I have always started with the left chest or non-button side and worked my way around in four sections. Maybe it's because I'm a lefty. You can start with the button side if you want. As you can see using the wide side of the ironing board gives you more area to work with.