Since being released from prison in one of Obama's final acts as president, she's assumed a low-key life as an independent woman in New York City.
But it seems Chelsea Manning is eager to share some parts of her new normal, according to the Daily Mail.
Wearing just a scarlet swimsuit and delicate necklace, the 29-year-old is seen in a Vogue photoshoot this month that is reminiscent of Caitlyn Jenner's famous Vanity Fair coming-out cover.
With her blonde hair cut in to a pixie crop and sporting minimal make-up, she beamed for photographer Annie Lebowitz's camera on a deserted East Coast beach.
Raising her hands to her salty wet hair to reveal her US$350 (NZ$481) Norma Kamali swimsuit, it is the first time her new look has been glorified in the pages of a magazine.
Later, she said she survived by avoiding television and hungrily reading books and science magazines. She did not address her two failed suicide attempts nor did she make mention of President Obama, who mercifully ordered her release in January, or President Trump, who has labelled her an "ungrateful traitor" since taking office.
Manning spent seven years at Fort Leavenworth Prison in Kansas for leaking almost 1million classified files to WikiLeaks while she was working as an army intelligence specialist in Iraq in 2009.
She was due to spend a total of 35 years behind bars but had her sentence suddenly and dramatically commuted by President Obama in January.
While behind bars, she kept up with fashion through magazines and avoided television, instead devouring books and science periodicals.
"I missed seven years of fashion, but I went through every season in a magazine!" she said.
Since being released, she has moved to New York City and is now living quietly in a downtown apartment. She has not seen her mother yet, she revealed, but intends to soon.
For now, she is enjoying being able to roam the streets unrecognised in dresses and skirts. Marc Jacobs is her designer of choice, she revealed, and was when she wore men's clothing.
As for work, Chelsea explained she is in the process of writing a memoir chronicling her extraordinary experiences and is also the star of a forthcoming documentary.
She hinted at running for office, telling the magazine: "I'm certainly not going to say no, and I'm certainly not going to say yes.
"My goal is to use these next six months to figure out where I want to go."
She is now an advocate for the rights of transgender people and was among protesters who descended on the White House last month when President Trump - announced a ban on transgender people serving in the military.
Formerly known as Bradley Manning, she revealed her transgender identity the day after being sentenced. In her Vogue interview, Manning recalls struggling with her identity during her Oklahoma childhood.
"I knew that I was different. I gravitated more toward playing house, but the teachers were always pushing me toward playing the more competitive games with the boys.
"I spent so much time wondering, What's wrong with me? Why can't I fit in?" she said.
She described juggling her gender and sexuality confusion with caring for her alcoholic mother and the feuding relationship she had with her father.
The internet was her solace, she said, and was where she discovered there was an LGBTQ community.
"Because I would actually be anonymous online, I could be more myself," she said.
At the age of 19, after bouncing between her separated parents homes in different countries and moving to Maryland to live with her aunt, she said she considered transitioning from male to female for the first time.
"It was the first time in my life when I really considered transitioning. But I got scared.
"I really regret the fact that I didn't know or realize I already had the love I needed, especially from my aunt and sister-just to seek support."
Desperate to learn more about herself and establish her identity, she enrolled in the military in the hope it would force order on her confusion and was later posted to Iraq.
In a brief and vague acknowledgement of leaking the classified files to WikiLeaks, she said: "I've accepted responsibility for my own decisions and my own actions."
She also recalled trying to give them to mainstream media publications including The Washington Post and The New York Times before handing them over to Julian Assange's website but said no one would listen.
She maintained that there are still not safe channels for whistle blowers to raise the alarm if they are concerned with government activity, explaining: 'We need to have more ways to talk about what's going on in government.
"I don't know what's right. I have certain values. I live by those."
Manning said she would remain in New York until late summer and then move back to Maryland where she spent time living as a teenager before joining the army.
She is struggling to keep up with social media which was in its infancy when she was jailed, but has enjoyed sharing photographs of her new life with fans on Instagram.
"Before I was in prison, I was one of the only people on social media. I was a novelty."
She did not address President Trump , who has repeatedly condemned Obama's decision to commute her sentence.