Recorder Peter Makepeace KC sentenced Jess Robert Collinson, 36, for possessing women's shoes and women's tights.
Collinson, 36, was jailed in 2010 for stealing a woman's shoes and again in 2013 for trying to snatch the shoes of a second woman on her way home. As a result, she is prohibited from wearing women's shoes in public under a Sexual Harm Prevention Order (SHPO).
KC Judge Guy Kjaer warned in 2013 that Collinson had an “obsession or fetish for women's shoes with stiletto heels”.
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Now Recorder Peter Makepeace KC has warned Collinson is at increased risk of committing further crimes to satisfy his fetish.
And he dismissed Collinson's claim that he had no idea the shoes were in his bag and belonged to his ex-partner.
“You carried those items with you for the purpose of sexual gratification,” he said.
He said he had read the probation report and assessed Collinson to be at “high risk” of committing further offenses related to his fetish.
He told York Crown Court: “The risk that sexually motivated offenses will cause serious harm is increasing and the risk of further offending is high.”
Collinson had no desire to address the reasons for his fetish and change himself, the court said.
The judge said, “I have no choice but to pass a prison sentence.''
Mr Collinson, of no fixed address, was jailed for six months after pleading guilty to breaching a sexual harm prevention order and criminal damage to a wall at a beach cafe.
Brooke Morrison, prosecuting, said Collinson removed three pieces of wood from the wall of the Clock Cafe in Scarborough at 8.20pm on December 14 so he could go inside and sleep. The cafe was closed for the winter.
He caused £3,500 of damage to walls and the cafe's owner told police his actions may have damaged the cafe's £13,500 commercial dishwasher beyond repair.
The judge said he sympathized with the cafe owner but could not order Mr Collinson to pay compensation because he was in prison and had no money.
Mr Morrison said Mr Collinson's actions triggered the cafe's alarm, which alerted police. They tracked him through local authority CCTV and caught up with him at another location in Scarborough at 9.45pm.
A pair of women's high-heeled shoes and women's stockings were found in his bag.
Ms Collinson told the court the shoes were in her bag and that she had no idea they belonged to her ex-partner.
In Collinson's case, Nick Peacock said he was trying to get into the cafe because he was homeless and had spent six weeks in prison on remand before his sentencing hearing.