Kelly's attorney, Steve Greenberg, who has previously denied all assault allegations against the R&B singer, also told the judge that Kelly has turned in his passport, though the 52-year-old has not been able to post bail yet. Kelly' next court date is scheduled for March 22, CNN reports.
Wearing an orange jumpsuit and flanked by sheriff's deputies, Kelly was in court Monday.
The not guilty pleas come a few days after Kelly was indicted on Friday on 10 counts of aggravated criminal sexual abuse against four victims, thee of whom would have been underage at the time of the alleged crimes.
On Saturday, Kelly's bond was set at $1 million. To leave custody he'd have to pay 10 percent of the total, or $100,000 — but he couldn't come up with the cash, with Greenberg alluding to financial problems.
"This is someone who should be wealthy at this stage of his career," Greenberg said, citing "mismanagement," "hangers-on" and "bad deals" as some of the reasons Kelly "really doesn't have any money at this point."
Until Kelly can come up with the bail money, he will continue to be transported between Cook County Jail and the courthouse, both of which have seen their fair share of star power in the last week or so, with Empire star Jussie Smollett being booked at the jail and heard at the courthouse as well.
Cook County State's Attorney Kimberly Foxx said that Kelly's alleged abuse took place over 12 years. Prosecutors say there is video that shows multiple sex acts, allegedly with Kelly and a 14-year-old girl.
But Greenberg said he doesn't believe the accusers. "I believe all the women are lying," Greenberg said.
High-profile attorney Michael Avenatti, who is representing one of the accusers, called Greenberg's statements "outrageous and completely unprofessional."
Avenatti reportedly played a role in getting key evidence in the hands of a grand jury in recent weeks, resulting in last week's indictment.
The attorney said that Kelly will likely face federal charges for his alleged crimes in the near future. "I expect R Kelly to also face federal charges in the coming weeks/months. These charges will be distinct from the crimes for which he was charged yesterday and will result in a separate criminal proceeding," Avenatti tweeted on Saturday. "Ultimately, R Kelly will rightly spend his remaining days in prison."