There are 12 words that start with 'simple'.
| simple | simpler | 
| simples | simplex | 
| simplest | simpleton | 
| simplexes | simpleness | 
| simpletons | simpleminded | 
| simplenesses | simplemindedly | 
Note: These 12 words that start with 'simple' are found from the USA & Canada version of the tournament Scrabble word list.