- You can set width (not height) of your menu item by using spaces, and then draw on empty space with OnPaint
- If you need to place picture into drop down why use ToolStripMenuItem? For example you can place ToolStripControlHost with Image embedded. And do not forget that you can change drop down layout by using LayoutStyle and LayoutSettings properties (for example from stack to table layout)
- You can not only specify size for your menu item, but you can also specify size for drop down where it located. For example when drop down is opening (OnOpening, Opening, DropDownOpending many ways to react) you can set minimum width (or height, or both) by using ToolStripDropDown.MinimumSize property.
In general ToolStrip is most properly architectured control in the WinForms namespace. It has almost unlimited possibilities and very extensible.
Update: According to your comment. I cannot say much, because while ToolStrip is most architectured it is also commented very good, and many particular things need to be discovered. I still added #3 to my answer, but many things can be discovered only by trying, and by using Reflector of course.