Leeds Crown Court heard Anthony Clarke had been jailed for eight years in 2012 for robbery and blackmail.
He was part of a gang who threatened two women with a claw hammer outside a prep school in Weetwood.
They eventually fled with two diamond rings, a Rolex watch and a designer handbag.
He was out on licence for those offences on April 14 this year when he crept up behind a woman as she walked to work in Lidgett Lane, Roundhay, at 6.50am.
Carmel Pearson, prosecuting, said Clarke grabbed the woman by her arms from behind, dragged her to the ground and was pulling at her handbag.
He stamped on her face as she bravely struggled, catching her on the chin. The blow caused her to let go of the bag containing her phone and cash, and he ran off.
The woman gave chase but Clarke jumped into a car and sped away. She contacted the police and was able to give them the number of the vehicle, which turned out to have been reported stolen in March.
Within 15 minutes Clarke went to shops in Roundhay Road and bought food worth £16 using her bank card.
However, he was captured on CCTV and identified by an officer who recognised him.
The court heard Clarke had 30 convictions for 64 offences including previous robberies.
Richard Reed, representing Clarke, said he had been released to a bail hostel and was doing well until he broke the rules by taking his girlfriend there.
“He was then living a fairly nomadic existence in Leeds,” he said.
“The complainant said he had the appearance of a tramp and essentially he committed this robbery so he could buy some provisions because he had none. He went straight to a local shop for some food.
“He bitterly regrets sabotaging things and is going to pay greater regard to the rules on his next release.”
Clarke, 44, of no fixed address, was jailed for five and a half years after he admitted robbery and fraud.
Judge Geoffrey Marson, QC, said Clarke had a terrible record and had no doubt targeted the woman thinking she would be a soft option.
When she turned out to be made of “stern stuff” and resisted, he stamped on her.
“It must have been a terrifying experience [for her],” he said.