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I have taken the plunge into adding free hand designs to my models recently, I am quite happy with my icons and small epitaphs but when it comes to banners and capes I realise my ability is some what below par. Even straight lines seem to elude me when painting free hand let alone complex images. Instead of honing my skills by ruining hundreds of pounds worth of models I wanted to know how others liked to improve their free hand ability. Any help is appreciated and pics would help inspire!

Paint on a piece of paper? Or random piece of plastic?

Try it on whatever you can get your hands on. Prime some sprue bits or old CD cases and try it on those. If you really want something to follow, pick up some cheap plastic army men at a discount store and paint those. Some FLGSs have bargain bins that you might be able to find some fun practice minis in. Metal ones in particular are great because they're really easy to strip clean again.

Small stuff first.
Simple designs like suns or tribal markings.
Dont try to paint a skull your first turn.