Windsor was born in Ipswich, Suffolk, and grew up in the Spring Road area. He attended Clifford Road Primary and Copleston High School. He began dancing at the age of three, when his parents took him to the Ipswich School of Dancing.[1] At age 15, Windsor moved to London to pursue his career as a dancer.[2]
In 2010, Windsor's first season of Strictly Come Dancing Kristina Rihanoff became his professional partner. [10] They performed Solo Routines on Strictly Come Dancing and have also taken their partnership off the Strictly Dance Floor, with them both headlining Burn the Floor in London's West End in 2013. The Partnership has taken them all over the World, from Charity events to Strictly Cruise Ship events, they have performed in the South African version of Strictly Come Dancing and teaching large groups at this special event.
From 2003 to summer 2010, Windsor was part of the cast of Burn the Floor,[15] one of the leading ballroom-based shows in the world. Two tours with Burn the Floor (2003, 2004) and three with FloorPlay (2006 to 2008) took him several times around the world, leading up to the highlights being a stint on Broadway (2009) and in the London West End (2010). In Windsor's last season with Burn the Floor in London, he was engaged in the role of Swing having to learn all male dancers' parts, to step in for any one who was unable to perform. From Broadway Windsor's abilities took him to Dancing with the Stars Australia and So You Think You Can Dance in Holland. He was also asked to assist in the choreography for the Australian version of So You Think You Can Dance.

In 2012 Windsor starred in Dance To The Music Tour along with his professional partner Kristina Rihanoff, fellow Pro Dancer from Strictly Come Dancing Artem Chigvintsev and Kara Tointon who won the Strictly Glitter Ball in 2010. With music from the Strictly Come Dancing Band the show toured the UK in a successful run.

In 2013 from 6 March to 30 June 2013 Windsor returned to headline Burn the Floor along with his professional partner Kristina Rihanoff, a hugely successful run in the heart of London's West End at the Shaftesbury Theatre.[16]