Born in Camden, Greater London, Hylton joined Aldershot Town aged 16 in 2005, when he was signed by Terry Brown. During the 2007–08 season, Hylton was part of the team which won the Conference Premier title and the Conference League Cup. Among his appearances, Hylton played in their first League Cup match, when he came on as a 69th-minute substitute for Marvin Morgan in a 3–1 defeat to Coventry City on 13 August 2008.

In March 2007, Hylton joined Harlow Town on loan before he sustained an injury on his debut, making one appearance as a result.

On 6 January 2011, it was reported Hylton had agreed to sign for AFC Wimbledon. However, he later signed a one-year contract extension to remain with Aldershot under new manager Dean Holdsworth.

In May 2012, Hylton was given an eight-match ban and fined £1,000 after being found guilty of two charges of racial abuse.

On 18 June 2013, Hylton signed a two-year contract with newly promoted League One club Rotherham United, with the option of a third year. He made his Rotherham debut in a 1–0 win away to Brentford on 5 October. Ten days later, Hylton was loaned out to League Two club Bury until 23 November.

On 27 January 2014, Hylton joined AFC Wimbledon on loan for the remainder of the 2013–14 season. Rotherham were promoted to the Championship at the end of the season, and Hylton was transfer-listed.

Hylton joined League Two club Oxford United on a two-year contract on 6 June 2014. He ended the 2014–15 season as Oxford’s top goalscorer with 16 goals in all competitions, 14 of which came in the league. On 3 April 2016, he scored Oxford’s second goal in the 2016 Football League Trophy Final at Wembley Stadium, which Oxford lost 3–2 to Barnsley.

Hylton turned down a new contract with Oxford to sign for League Two club Luton Town on a two-year contract on 31 May 2016. He scored the opening goal on his debut in Luton’s 3–0 win away to Plymouth Argyle on the opening day of 2016–17. Hylton scored a hat-trick for Luton in a 4–1 win at home to Wycombe Wanderers on 3 September, which saw him earn a place in the English Football League Team of the Week. He scored twice from the penalty spot for Luton in a 3–1 victory away to Exeter City in the FA Cup first round, ensuring their progression to the second round. Hylton signed a contract extension with Luton on 12 January 2017 until June 2019, with the prospect of a further extension until 2020, having scored 14 goals from 26 appearances up to that point in 2016–17. He scored twice during a home match against Crawley Town on 11 February, the first coming in the 70th minute and the second coming in the 76th minute, which made the score 2–1 to Luton, and was once again named in the English Football League Team of the Week. Hylton was named the PFA Fans’ League Two Player of the Month for February 2017, during which he scored four goals in five league appearances. His performances for Luton saw him named in the PFA League Two Team of the Year, as well as being named Luton Town Player of the Season, voted for by the club’s supporters. Hylton played in both legs of Luton’s play-off semi-final defeat to Blackpool, which finished 6–5 on aggregate, and scored a penalty in the 3–3 home draw in the second leg. He finished the season with 47 appearances and 27 goals.

Ahead of 2017–18, Hylton had an operation on his lower leg which saw him miss the start of the season. His first appearance of the season came against Tottenham Hotspur U21 in an EFL Trophy group stage match on 15 August 2017, in which he was substituted at half-time. Hylton scored his first goal of 2017–18 in his 50th appearance for Luton with the equaliser away to Mansfield Town 11 days later, which finished a 2–2 draw. He was named the PFA Fans’ League Two Player of the Month for October 2017, having scored four goals from five league appearances.