Custom content box (img) in sidebar that adjusts depending on material

You are, probably, approaching it in the wrong way.
You should apply that “box design” via your stylesheet to the sidebar elements: lists, widgets etc. That’s how WP designers do it.

If you are a complete “noob” to CSS… then you will have to learn the basics. There isn’t really a magic workaround to avoid that.
CSS
Customizing_Your_Sidebar
Styling_Lists_with_CSS

Hey Moshu, thanks. I’m sure it can be done this way, as I’ve come across this guys blog at https://www.daimos.de that uses this same method for the actual blog entries. I’m trying to learn css right now, its just that I’ve got a full plate on my hands. Is there anyone that could show me the basic code for something like this? Can someone give me a quick rundown of the css styling that I wlll need, and the html that I’ll need to place into my singlesidebar.php

Thanks

These are the 3 images that I am working with.
https://www.atriskstoriesofhope.com/wordpress/wp-content/themes/default/images/cboxfeedtop.jpg

https://www.atriskstoriesofhope.com/wordpress/wp-content/themes/default/images/cboxfeedmiddle.jpg

https://www.atriskstoriesofhope.com/wordpress/wp-content/themes/default/images/cboxfeedbottom.jpg

There is a big difference between what you are trying to do and what daimos is doing. That site uses rounded corners on the boxes which can only be achieved using background images.