NEW YORK (Court TV) — Imagine J.Crew offering marital advice with its sweaters or The Gap dispensing job tips with its T-shirts, and you'll have some idea of what Adrienne Smalls' merchandise company does for Empire State inmates and their families.

Smalls, dubbed "the L.L. Bean of the New York Prison system," sells everything from tube sox to hair gel to those incarcerated in 31 of the state's correctional facilities. But aboard the buses that shuttle relatives from Manhattan to upstate prisons and on her popular Web site, www.prisonhelp.com, Smalls is known as a compassionate guide through the criminal justice system and a one-woman testament to hope beyond the prison walls.

"The name of the business is exactly what it is — prison help. Not just selling, but help," she said. "The sense that there is somebody who has been there, done that and will go the distance with you — that's me."

Smalls has no trouble relating to her clients. The 44-year-old Bronx woman spent three years in jail for hitting a police officer, and her son did five years in state prison for a drug offense.

Some of the products Smalls provides

"With me and my son being ex-cons, we have credibility. In a lot of jobs, it would be against us, but not here," she said.

Smalls' business has two components. She sells toiletries and other items to prisoners' relatives who take bus trips, some as long as 36 hours, to visit inmates. She also sells merchandise to prisoners themselves, through the mail or through relatives. Smalls' most valuable asset is her comprehensive knowledge of what will be accepted by corrections officials and what will be rejected. Each prison's rules are slightly different, often leading to frustration for families and anger for inmates.

"You go up there with a box of stuff, and you'll come back with more than half of it," said Smalls. Black knit caps, for example, are permitted at most facilities, but at the prison in Clinton, N.Y., only green caps are acceptable. Lotion is permitted, but not if it has a pump top or contains alcohol or is in an unsealed container. There are similar rules for boots, thermal shirts and shaving cream.

For prison families who find gifts for their loved ones rejected, Smalls said, "You get mad and you just spent a day on a bus and now you are carrying everything back with you? It makes you want to stop coming and for the person on the inside, they are going to have a beef with the guy in the package room."

On one return trip from visiting her son, Smalls said she looked at the items officials had turned away and asked herself, "Is everyone having the same problem?" The question sparked an idea for a business. Smalls said she has spent years nailing down the regulations at each facility and finding products that comply.

"My lotion," she bragged, "is special. No one will ever know what's in it."

Smalls' Web site is more informational than commercial. In addition to news articles about prisons, the site includes visiting schedules for Rikers Island and bus schedules to other prisons. Customers can peruse her order form and look at pictures of the merchandise.

"Anything pertaining to the prison system is interesting to you when you have someone inside," said Smalls.

Customers can order goods through e-mail or fax, but Smalls does not take credit card orders online.

"I'm in a business where I'm dealing with criminals. I have to minimize the risk," she laughed. "I know how easy identity fraud is."

Smalls said the site gets about 500 hits a week, and she hopes to increase the number of visitors by developing a new address that doesn't contain the word "prison."

"Big brother is watching, you know? People might want to pull it up at work, but they worry that the boss may see and say, why are you looking at something with [the word] 'prison' in it," said Smalls.

Around the clock, she fields e-mails and phone calls and faxes from concerned relatives. They want to order a pair of Timberland boots — her best-selling item — but they also want to know how to finesse a dispute with jail officials. Or they want advice about how to keep a family together while its leader is behind bars. When inmates are released, she refers them to job training programs.

"It's very difficult," she said. "I just listen to them. Whether or not they belong [in prison], that's not my call."

Still, she draws the line. Smalls will not deal with prisoners serving time for sexual assault or abuse.

Deborah Sanders, executive director of the Harlem Venture Group, a financing support group that named Smalls "entrepreneur of the month" last summer, called her "the grandmother, the queen, really, of prison suppliers."

"A lot of her customers certainly relate to her," said Sanders. "People feel more free to talk about relatives who are locked up. She brings a great deal of dignity to it."

More Caught on the Web