The 50 Best Taylor Swift Songs for Every Era and Every Mood

We may be shipping Joe Alwyn and Paul Mescal while side-eyeing Tay Tay for her whirlwind whatever-that-was with Matty Healy. But her questionable relationship choices have given us some of the most singalong-worthy love and breakup songs. So as far as we’re concerned, Taylor, go get your (next) man.

But whether the topic is romance, heartbreak, fame, or growing up, the best Taylor Swift songs all have one thing in common: stellar storytelling. And with 19% of Grindr users naming music as their top hobby, this list feels especially relevant. Here’s a roundup of our faves from each era.

Songs to dance to

Era: Debut

1. “A Place In This World”

The songwriter hadn’t yet turned superstar when she wrote, “I don’t know what I want, so don’t ask me, ’cause I’m still trying to figure it out.” By now, she certainly seems to have found her place.

2. “Our Song”

Taylor uses her poetic genius to paint a picture of the romance every teenager dreams of in this carefree song that’s a little bit country, a little bit pop, and a whole lot of fun.

Era: Fearless

3. “Mr. Perfectly Fine (Taylor’s Version) (From The Vault)”

Taylor was still bitter about her breakup with the hottest Jonas brother when she penned the lyrics to “Mr. Perfectly Fine.” But they’re friends now, and Joe openly supports her re-recordings — even when she roasts him like a pig on a T-Swizzle stick.

Era: Speak Now

4. “Mean”

This certified Swiftie fave puts a fun spin on putting bullies in their place.

5. “The Story of Us”

Ever had an awkward run-in with an ex? Taylor has, and it inspired a killer song that lays out the rise and fall of the relationship, storybook-style.

Era: Red

6. “22 (Taylor’s Version)”

“We’re happy, free, confused, and lonely at the same time. It’s miserable and magical.” There’s no better college kid anthem than this.

Era: 1989

7. “New Romantics”

A prime example of Taylor’s shift from country-pop to synth-pop, you’ve probably heard “New Romantics” piping through the speakers at H&M. It might be overplayed, but that’s just because it’s catchy af.

8. “Style”

Taylor’s ode to her toxic relationship with the one and only Harry Styles. Who can blame her for getting sucked in by that James Dean daydream look in his eye? We’d fall for it too.

Era: Reputation

9. “…Ready For It?”

Taylor fell off the face of the earth in mid-2016, reemerging nearly a year later with black lipstick and a taste for blood. “...Ready For It?” was the second single on reputation, and the music video remains a fan fave.

10. “Getaway Car”

What do you do when you’re just so over Calvin Harris? If you’re Tay Tay, you use Tom Hiddleston as a getaway car and then write a song about leaving both of them in your dust.

Era: Lover

11. “Cruel Summer”

This song may or may not be about Kanye, Joe Alwyn, or Taylor’s mom’s breast cancer diagnosis. But don’t let the sad subject matter fool you — “Cruel Summer” is the perfect summer anthem.

12. “Paper Rings”

In the cutest love song about Joe Alwyn, Taylor sings about the night they met: “Went home and tried to stalk you on the internet.” T Swift — she’s just like us.

Era: Folklore

13. “august”

The storytelling throughout all of folklore is next level, but “august” manages to rise above the rest, telling the tale of a teenage side piece who loses her virginity to a boy who was never really hers. Listen for the lyrics, stay for the transcendent instrumental break at the end.

Era: Evermore

14. “no body, no crime (feat. HAIM)”

Some Swifites seem to think every song is based on Taylor’s life, but we hope this one’s not. If you’re intrigued by murder (who isn’t?!), “no body, no crime” is for you.

15. “willow”

Taylor strayed from the typical country and pop songs of her past for folklore and evermore, opting for a calmer indie-folk vibe. She collaborated with The National’s Aaron Dessner for the witchy “willow,” which sounds like a love spell set to music.

Era: Midnights

16. “Anti-Hero”

“Anti-Hero” topped the Billboard Top 100 for a record-breaking eight weeks. The song says she’s the problem, but with ratings like those, it seems she’s got things pretty well under control.

Songs to cry to

Era: Debut

17. “Teardrops on My Guitar - Pop Version”

No list of Taylor Swift songs would be complete without a taste of the new-country music that launched her career.

Era: Fearless

18. “The Way I Loved You (Taylor’s Version)”

Healthy relationships just don’t seem to do it for Tay. Even when she’s found the perfect-on-paper man, she misses “screaming and fighting and kissing in the rain.”

19. “White Horse (Taylor’s Version)”

In this fairytale gone wrong, Taylor realizes that even Prince Charming knows how to let her down.

Era: Speak Now

20. “Back to December”

Tay Tay has a lot of positive traits, but accountability isn’t usually one of them. Taylor Lautner should consider himself lucky for being the exception in this heartfelt apology song.

21. “Dear John”

John Mayer, on the other hand? Taylor dragged his ass in “Dear John.” Taylor Lautner even made a TikTok praying John survives the aftermath of the songs coming out of the vault for 2023’s Speak Now (Taylor’s Version).

Era: Red

22. “Nothing New (feat. Phoebe Bridgers) (Taylor’s Version) (From The Vault)”

From depression to misogyny to identity crises, the struggles outlined in this so-called “big sister song” couldn’t be more relatable to Taylor’s target demographic.

23. “All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault)”

In this extended version of 2012’s “All Too Well,” Taylor dives even deeper into the intimate memories she created with Jake Gyllenhaal, even bringing the story to life in a short film. Where’s the scarf, Jake?

Era: 1989

24. “Clean”

In her 2020 documentary, Miss Americana, Taylor gives a mid-concert speech about beating the defamation charges brought against her by a DJ she’d accused of groping her. She then performs “Clean,” and suddenly lyrics like “Gone was any trace of you, I think I am finally clean” sounded less like someone getting over a love addiction and more like a victim shedding the pain of sexual abuse.

Era: reputation

25. “New Year’s Day”

It’s normal to worry about who you’ll kiss when the ball drops on New Year’s Eve. But the real ride-or-die romance happens who’s there to feed you Advil when you’re nursing a hangover the next day.

Era: Lover

26. “The Archer”

All about Taylor’s tendency to self-sabotage in every relationship, “The Archer” will bring you to tears for real.

Era: folklore

27. “this is me trying”

Even Taylor isn’t immune to the feeling of trying so hard — and just making everything worse.

28. “the lakes - bonus track”

“Take me to the Lakes where all the poets went to die,” sings Taylor, referring to England’s Lake District, the most romantic place in the U.K.

Era: evermore

29. “champagne problems”

This song about a woman who refuses a marriage proposal because she’s too mentally ill for commitment is way more relatable than the name suggests.

30. “tolerate it”

“I know my love should be celebrated, but you tolerate it.” This one stings because it’s true of far too many couples.

Era: Midnights

31. “Midnight Rain”

He wanted a quiet life, she wanted fame. He’s the sunshine, she’s the midnight rain.

32. “Would’ve, Could’ve, Should’ve”

In “Dear John,” Taylor talks a lot about what she “should’ve known” when dating the much older John Mayer. “Would’ve, Could’ve, Should’ve” revisits the relationship from an older, wiser perspective, talking about what hindsight tells her she would have and could have done differently — but never saying what she should have done, because the only one who should’ve known was John.

Songs to swoon to

Era: Debut

33. “Mary’s Song (Oh My My My)”

Just a wholesome love song about two small-town kids who fall in love and grow old together.

Era: Fearless

34. “You Belong With Me (Taylor’s Version)”

In one of Tay’s most beloved music videos, the superstar plays the role of both her crush’s mean girlfriend and the “not like other girls” main character.

35. “Love Story (Taylor’s Version)”

An iconic song with an iconic music video about the most iconic love story ever — Romeo and Juliet.

Era: Speak Now

36. “Sparks Fly”

Here’s a disclaimer that we probably should have put at the top of the list: Don’t take love advice from Taylor Swift. “Sparks Fly” is yet another song about falling for a hot guy who doesn’t pass the vibe check. But hey, at least it’s a banger.

37. “Enchanted”

Sometimes sexual chemistry feels like actual magic.

Era: Red

38. “Begin Again (Taylor’s Version)”

If you dated a guy who went to jail for defending a friend when someone called him a gay slur, you’d write a song about him too. Oh, and did we mention he’s a Kennedy?

39. “Everything Has Changed (feat. Ed Sheeran) (Taylor’s Version)”

Taylor teamed up with the debatably adorable Ed Sheeran for this undeniably adorable duet.

Era: 1989

40. “This Love (Taylor’s Version)”

A more poetic take on Taylor’s time with everyone’s favorite toxic hottie, Harry Styles.

41. “Wildest Dreams (Taylor’s Version)”

“His hands are in my hair, his clothes are in my room.” This one is certified s-e-x.

Era: reputation

42. “Dress”

Somehow even hornier than “Wildest Dreams.” Joe Alwyn got Taylor down so bad her hands were shaking.

Era: Lover

43. “Daylight”

Joe must have given Tay what she needed because she calmed down for this one, realizing love doesn’t need to be burning red — it’s golden like daylight.

44. “Lover”

Taylor single-handedly ruined the concept of love for Swifties everywhere by penning the perfect song about finding your other half and then … breaking up with Joe. Rude.

Era: folklore

45. “cardigan”

The lead single from folklore and one of three songs from the album’s love triangle, “cardigan” is sung from the perspective of Betty, a broken woman whose man supported her through all her hardships — many of which he created.

46. “betty”

Remember the teenage side piece in “august”? She was sleeping with Betty’s man, and we get his side of the story in “betty.”

47. “invisible string”

Another sweet song about Joe! “One single thread of gold tied me to you.” Well, snip snip. He’s Paul Mescal’s man now.

Era: evermore

48. “‘tis the damn season”

This one gives Hallmark Channel meets fuck buddy. They only hook up when she’s home for the holidays, but he’s always in the back of her mind.

49. “ivy”

This sensual song about stepping out on your husband uses plant imagery to get us hot and bothered. Oh, Taylor. Clever girl.

Era: Midnights

50. “Snow On The Beach (feat. More Lana Del Rey)”

It’s not every day you fall in love with someone at the exact same moment they fall for you. It’s as surreal as seeing snow fall on the beach, you might even say. Fans were salty when the Lana they were promised in the original wasn’t the Lana they got. So Taylor solved the problem in a very Taylor way: by re-releasing the song with a deliciously passive-aggressive promise of “more Lana Del Rey.”

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