Take a simple real life example: Monday, a presentation, a conference room, for two hours you stand and gesture. Slim looks great when you walk in, but if it is even slightly too narrow at the shoulders, after fifteen minutes you start adjusting it. A well chosen regular lets you focus on the conversation. On the other hand, if after the presentation you go to a client meeting and put on a jacket, an overly loose regular can bunch at the waist, making your whole silhouette look heavier.
At ceremonies where photos are taken, a slim shirt often works in your favor because less fabric creates fewer folds at the stomach and waist. But there is a catch: photos are also taken while sitting. If slim is too tight, in a seated position the buttons strain, the collar can feel like it is choking you, and the cuff creeps away. Then it becomes obvious the shirt is not fitted, it is just too small. Regular in the same situation stays calm because it has reserve.
If you are putting together a look for a more formal evening, I often start with a shirt with a predictable collar and cuff, and only then choose accessories. You can add a tie, for example the Krawat Classico, which ties neatly and works with many jackets. Then the question “slim or regular shirt” is about whether the knot and collar will look proportional to your neck and face, because a too tight shirt ruins even the best tie.
If you want to go deeper into workwear, especially in warmer months, our guide Business dress code: how to dress in summer? will be helpful. We show how to think about breathability and when it is better to skip overly fitted forms. A shirt should look elegant, but it should also breathe, otherwise you will simply look tired.