Recently I've been working in order to create for Uritec a new plugin for CKEditor, it was needed due to the way that the Style system works in CKEditor.
First the Styles dropdown shows the styles that can be applied to the current element as well as its container(s); look at the official demo and select the image, now click on the Styles selector and you'll see there "Object Styles", "Paragraph Styles" and "Character Styles", something that it's not too user friendly if they just want to modify the image. The normal user wants simple things.
The second main problem is that even if they focus just on the Object Styles, you (as page author/designer) can't restrict the way that the styles work between them, so if you want to use a class to apply a 1px gray border, and a different class to create a slight rotation and shadow, the user can't apply both at the same time (unless you apply inline styles that we all know it's bound to fail).
So the goal was to allow to apply groups of classes that can be mixed so you set one group of classes to define different types of borders and another one to apply color filters, etc... Also, let's keep in mind that the align center has been disabled in CKEditor for those who prefer to use the classic Image plugin although it's easily done using display:block and margin:* auto, so one obvious group is alignment.
Putting all those buttons to show up always in the toolbar was considered a bad idea because most of the time they won't be used, and providing instead a "contextual" toolbar that shows only when an image is selected was considered the best option.
Taking all of that into consideration ImageToolbar was born, designed to work in both classic (framed) editor as well as new inline mode, and compatible with the normal Image plugin and the Enhanced Image plugin. You can play at its demo with some predefined styles, but you can define whatever you want as long as you're able to do it with CSS classes. Or if you feel lazy today, check the 1 min. demo on YouTube.
If you use the Enhanced Image plugin you should know already that the way to define your CSS file requires taking some extra care, we have added some notes about it in a small guide about styling images in CKEditor, and due to those widget wrappers and upcast/downcast you'll find that it's much more powerful when you configure ImageToolbar with the classic image as you aren't restricted by the "Enhanced image" limitations.
Lastly, remember that unlike other plugins that claim to be free but then require you a monthly payment, this is a one time payment that will give you any future update.