In an interview with French television, Putin was asked about Clinton's recent remarks that the Russian leader was trying to redraw the boundaries in eastern Europe just like Adolf Hitler did in the 1930s.
"It's better not to argue with women," Putin replied, adding: "But Mrs. Clinton has never been too graceful in her statements."
Putin remarked that he met Clinton when she was the US top diplomat "and had cordial conversations at various international events. I think even in this case we could reach an agreement".
But as the Russian leader has come under fire in the West for his aggressive policies in Ukraine and Moscow's annexation of Crimea, he did not hide that he found Clinton's Hitler-like comments extreme.
"When people push boundaries too far, it's not because they are strong but because they are weak," said Putin, who then went on.
"But maybe weakness is not the worst quality for a woman."
First Lady when her husband Bill Clinton was in the White House, Hillary Clinton has become a political force in her own right and an idol of feminists who hope to see her become the first US woman president.
She was a presidential candidate in 2008 but lost the Democratic Party nomination to Barack Obama, who after his election victory asked her — then a senator from New York — to head the US State Department.
Clinton chose not to continue in that post after Obama won a second term in office in 2012, but speculation has been rife that she is planning another run for the White House in 2016.
The French reporters pressed Putin about whether he wanted to get back at Clinton or laugh it off.
"Someday I will indulge myself and we will laugh together at some good joke," he responded.
But Putin didn't stop at that.
"When I hear such extreme statements, to me it only means that they don't have any valid arguments.
"Speaking of US policy, it's clear that the United States is pursuing the most aggressive and toughest policy to defend their own interests — at least this is how the American leaders see it — and they do it persistently."
As for America's current leader, President Obama on Wednesday condemned Moscow's "dark tactics" in Ukraine where the new pro-West Kiev government is battling a pro-Russian insurgency in the east of the country.
Obama and Putin will come face-to-face on Friday in France at the 70th anniversary commemorations of the D-Day Normandy landings in World War II.
No formal meeting between the two is planned.
"It is his choice, I am ready for dialogue," Putin said of Obama in the interview with French broadcasters Europe 1 and TF1 conducted at his dacha in the Black Sea resort of Sochi.