Transsexual Tina Cook, 54, signed on for Jobseekers allowance last year after losing her job as a labourer for Carillion.
Miss Cook, who was born Andrew, is technically still a man and is yet to undergo the physical transformation of her body through hormone treatment and surgery, which will take a further three years.
She has to live and dress as a woman every day for a year as part of her gender realignment treatment.
But Cook claims Jobcentre employees in Darlington were insensitive to her situation and advised her to dress as a man for interviews.
She told the Daily Mail: “I’ve only recently summoned the courage to be the way I want. I have given up so much.
“My family don’t really talk to me and I have no friends. How can they expect me to give it up to get a job? It’s really insensitive.
“I don’t go to the Jobcentre for disrespect and abuse. All I need to do for that is walk down the street or go into any pub.
“I don’t expect it when I am trying to get off benefits and get back into work. I know they are making fun.
“I get the feeling when I go to the Jobcentre sometimes that they don’t want me there.
“When they see me, they try to make me go to interviews for waitressing jobs at posh restaurants, but my forearms are covered in tattoos. There is no chance I’d get those jobs.”
Cook said she first began questioning her gender aged six and had spent decades going to work as a man before dressing as a woman when she got home.
After losing her job she decided to remain as Tina permanently.
Since then she has had around 30 interviews, mostly for cleaning and driving jobs or kitchen work, none of which has been successful.
Cook has now lodged a formal complaint with the Department for Work and Pensions and has also taken legal advice.
A Department for Work and Pensions spokesman said: “Jobcentre Plus is committed to treating all individuals fairly and equally.
“We are aware of this complaint and are investigating.”