Choose the mood before the details
Start with where you are going and how you want to move through it. For an easy daytime look, a shorter or midi-length caftan with flat sandals keeps everything uncomplicated. A floor-skimming length can feel more dramatic with almost no extra effort. If the plan calls for a little polish, look for a neckline, sleeve or print that already feels intentional, then resist the urge to add too much around it.
The most wearable caftan is not necessarily the boldest one. It is the one that makes getting dressed feel simpler. Think about the colors you return to, the amount of coverage that lets you relax and the pieces already waiting in your closet. A versatile caftan earns its place because it can meet you in more than one mood.
Fit should feel free, not formless
A beautiful caftan has breathing room. The fabric should fall away from the body enough to move when you walk, sit and reach, while the shoulder line and neckline still feel secure. Length matters as much as size: a hem that lands above the ankle reads more relaxed, while a longer line can feel quietly formal. Try it with the shoes you expect to wear most often before deciding.
If you like a little shape, use a narrow belt as an option rather than a correction. It can define the waist for dinner, then disappear the next day when you want the dress to drape. This flexibility is the point. You are not choosing between comfort and presence, you are choosing how much of each you want that day.