Putin chose the waters of the frozen Lake Seliger, in the Nilo-Stolobenskaya Monastery about 250 miles north of Moscow, for his plunge.
Vladimir Putin has joined millions of Orthodox believers to plunge bare-chested into icy water in a Russian tradition marking the Epiphany.
It is celebrated in the memory of the baptism of Jesus Christ in the River Jordan.
Stripping down to just swimming trunks, the 65-year-old lowered himself into the lake wearing a crucifix and fully submerged himself before quickly making his way out.
For President Putin, this is not the first Epiphany dip experience. In Russia and other Orthodox countries, the twelfth day after Christmas marks the Biblical revelation of Jesus as the son of God to the three wise men.
Orthodox Christians in Georgia and across the world are celebrating the Epiphany today, during which the Georgian Orthodox Church holds a mass baptism and conducts water blessing rituals.
In 2007, the now famous pictures of him emerged hunting topless.
It was the first time that Putin had participated in the ritual, although his spokesperson Dmitry Peskov later claimed that he had been "plunging into an ice hole for a number of years now".
The U.S. ambassador to Russia, Jon Huntsman, was also scheduled to take part in an Epiphany ceremony on Friday, state media reported.