Taylor Swift began taking vocal and singing lessons at a young age after generating interest in music. Nashville record labels rejected her, so she went to Big Machine Records to pitch her songs. With the release of her single Tim McGraw and self-titled debut album in 2006, Taylor Swift slowly became a popular name in the music industry. With the release of her follow-up albums, Swift broke many records and won 11 Grammy awards for her impactful music. Through her brand endorsements, music, and world tours, she has amassed a whopping $400 million fortune.

As one of the most popular female singers, Taylor Swift has been in the public spotlight from a young age with a public interest in her relationships. Her tricky love life has always been reflected in her songs, where she often mentions her ex-boyfriends. Let’s look at the ranking of Taylor Swift’s boyfriends based on their net worth.

10 Lucas Till ($2 million)

Lucas Till and Taylor Swift first met in 2009 when they shot her music video for You Belong With Me. According to Yahoo News, they dated for a short time but wanted to remain friends instead of deeper into the romantic aspects of their relationship still is best known for playing Havok in the X-Men series.

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9 Joe Alwyn ($4 million)

Taylor Swift famously mentioned in one of her songs that she met Joe Alwyn at the Met Gala. The pair were first spotted together in 2017 but have kept their romance relatively private. Going strong after five years, Alwyn is a British actor who starred in various period movies, including The Favorite and Mary Queen of Scots.

8 Conor Kennedy ($10 million)

Conor Kennedy is a socialite who is the grandson of Robert Kennedy Sr. and is often spotted at the family’s charity events and shows. Kennedy and Swift dated in 2012 and were first spotted visiting the cemetery to pay respects to Conor’s late mother. Their romance ended after the summer, but his family inspired Swift to write Starlight on her album Red.

7 Tom Hiddleston ($25 million)

Tom Hiddleston became a global superstar after taking on the role of Loki in the Marvel Cinematic Universe. His breakthrough in 2012 with Thor has helped him build his acting career. Taylor Swift first met Tom Hiddleston during the Met Gala in 2016, and the pair shocked everyone when they were spotted kissing in Rhode Island, as noted by Page Six. They were often photographed traveling the world; however, they called it quits after a few months.

6 Taylor Lautner ($40 million)

The Taylors met on the set of Valentine’s Day, where they played a typical high school couple. Their romance fizzled out after it was reported that Swift wasn’t very into the relationship and even apologized with Back To December. Lautner became a phenomenon after starring as Jacob Black in The Twilight Saga and made millions from the back-end profits.

5 Joe Jonas ($40 million)

Joe Jonas has been a recognizable face in Hollywood from a young age for being with The Jonas Brothers since 2005. Jonas has also starred in Disney shows and pursued a solo career. Taylor Swift had her first high-profile relationship with him in 2008, but they broke up within a few months. Swift called out Jonas on Ellen for breaking up with her over a 25-second phone call.

4 John Mayer ($70 million)

While John Mayer and Taylor Swift only had a relationship that lasted for three months, it remains one of the most memorable. After their split in February 2010, Swift wrote Dear John, a direct mention of him for her album Speak Now, as stated by Cosmopolitan. Mayer is an accomplished singer who has been critically and commercially successful with several Grammys.

3 Jake Gyllenhaal ($80 million)

Jake Gyllenhaal’s four-month romance with Taylor made a possible mark on the singer as she wrote two songs about him for her 2012 album Red. Their relationship has been infamously known for the red scarf that Swift mentioned in All Too Well. The actor broke up due to their 10-year age gap. Gyllenhaal is an established actor who has starred in notable projects like Brokeback Mountain, Nightcrawler, and Nocturnal Animals.

2 Harry Styles ($100 million)

Harry Styles is a member of One Direction, one of the most popular bands during its active years. Styles has since embarked on a highly rewarding solo music career and has ventured into movies. His relationship with Taylor Swift only lasted for a month, but the meaningful time led to multiple Swift hits like Out Of The Woods, and I Knew You Were Trouble.

1 Calvin Harris ($300 million)

Taylor Swift had her second-longest relationship with Calvin Harris, and the couple even celebrated their first anniversary in 2016. As mentioned by Elle, Swift and Harris made public appearances at award shows and even went out on dates before parting ways. Harris makes more than $30 million each year from his residencies and music and is the richest DJ in the world.

While it took Taylor Swift a long time to find the right partner, she has had a happy and healthy relationship with Joe Alwyn since 2017. The couple has also collaborated on multiple songs and supported each other’s careers. Swift is set to release her highly anticipated tenth studio album Midnights on October 21, 2022.

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Sources: Yahoo News, Page Six, Cosmopolitan, Elle

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