At the base of 500 South Sutter Street, Jasmine Pete tilted her chin skyward.
The 24-year-old in worn Adidas sneakers, hand-me-down Capri jeans and a black windbreaker examined the nine-story building from her spot on the sidewalk. She'd never been to San Francisco's financial district before.
She opened the glass door, waved to the smiling security guard and pressed "2" inside the elevator. On a quiet floor lined with offices, she spotted the room label that was also her mission: "Dress for Success."
Pete, a recovering crack cocaine addict, is among a growing community of formerly homeless women preparing for the work force in San Francisco.
Her local treatment center, Walden House, offers skill training for entry-level jobs.
When clients are ready to start interviewing, mentors make an appointment with Dress for Success.
It's all part of a charity-driven network, said Prenatal Homeless Program spokeswoman Martha Ryan. Treatment facilities and homeless shelters send women to local non-profit clothing agencies for an education in workplace fashion.
But for volunteers and clients alike, questions often arise: What qualifies as acceptable professional style in San Francisco? And how can it be created on the most basic level?
"There really isn't just one standard," local career couch Kate Blake said.
When tech companies like Twitter and Google began filling office buildings, super dressy duds started to phase out of professional closets.
However, she said, it's never a bad idea to polish for an interview. That's the most crucial time to impress employers.
For this reason, Dress for Success supplies interview apparel to women in Pete's situation: They must find work, and the right outfit helps.
Each client may select one free ensemble for an interview and, after she's hired, another for the workweek.
"It's amazing how much confidence one outfit can bring," said program manager Kate Lillig. "We dress women to empower them."
Clients are evaluated for clothing needs based on the nature of their potential job. Office positions require conservative apparel, while retail store managers admire trendy get-ups.
Clothing is available on a donation basis, so volunteers adhere to fashion icon Tim Gunn's philosophy: Make it work.
It's image consultant Elyse Freeman's favorite style challenge.
Across the street from Dress for Success's building, she styles homeless and disabled women at non-profit clothing store A Minor Miracle. Freeman favors solid colors and simple cuts in a city without a consistent work dress code.
"I think, 'How can I create the most re-wearable look?'" she said. "I want women to be able to mix and match at home to get the most use at work."
Freeman continuously searches the store, which also sells heavily discounted designer items to the public. Red heads look great in jewel-toned suits, she said. Blondes are most flattered by pastels.
And on the streets of San Francisco, every professional woman looks fierce in a towering pair of heels.
"Sometimes the women get emotional and almost cry," Freeman said. "They're finally ready to take on the world. I believe the best style, especially in big cities, is anything that gives you confidence."
Schyneida Williams sought Freeman's help for her first job interview.
After transitioning from homeless to self-supporting last October, Williams knew she needed workplace staples.
"I was wearing regular blue jeans and a sweatshirt when I walked in," she said. "I left with a bunch of stuff, like this awesome purple sweater, that I never would've thought to try on."
Now a case manager at the Prenatal Homeless Foundation, Williams refers other women to the clothing program.
Lovely clothes make all the difference, she said. It's important to let personality shine through at work.
Inside the Dress for Success lobby, Pete wondered what look would be best for her.
"Right over here," a volunteer said, ushering her into a room packed with suit jackets, casual blazers, dress pants and pencil skirts. "Our intern, Stephanie, will help you out."
Stephanie jotted down Pete's sizes and began leafing through the stuffed clothing racks. She paused to consider a beige Ann Taylor jacket.
"How about this?"
"I don't know," Pete said. "What about something younger?"
"Okay, what about this?"
Forty-five minutes and seven outfits later, Pete emerged from the single dressing room in a white pinstriped jacket and skirt from Dress Barn paired with black Chinese Laundry kitten heels. Matching rhinestone studs glittered from her ears.
She imagined walking into BCBG, an upscale clothing retailer near Union Square where she had an interview at 6 p.m. the next day.
She looked into the mirror.
"This is the one."