15 Underrated Taylor Swift Songs You Should Hear

15 Underrated Taylor Swift Songs You Should Hear

Taylor Swift has written hundreds of songs across ten studio albums, but some of her most beautiful work hides in plain sight.

While hits like Anti-Hero and Shake It Off dominate the radio, countless album tracks and bonus cuts deserve just as much attention.

These 15 underrated gems showcase her storytelling magic, emotional depth, and musical evolution in ways that even longtime fans might have overlooked.

1. Stay Beautiful (2006)

Back when Taylor Swift was just a teenager with big dreams and a guitar, she tucked this absolute treasure onto her debut album.

Stay Beautiful captures that magical moment when you admire someone from afar with pure, unfiltered sweetness.

The lyrics paint pictures with crayons instead of oil paints—simple, honest, and utterly charming.

Lines about Cory’s eyes and hoping he stays beautiful forever feel like reading someone’s actual diary from high school.

What makes this track special is its innocence, something that would naturally fade as Taylor grew up and experienced heartbreak.

It’s a time capsule of young love before complications arrived, wrapped in classic country twang and genuine emotion that reminds us where her storytelling journey began.

2. The Lakes (2020)

Hidden as a bonus track on Folklore, The Lakes reads like a love letter to the Romantic poets Taylor admires.

She name-drops Wordsworth while dreaming of escaping modern pressures for quiet solitude beside tranquil waters.

The production feels deliberately old-fashioned, with sweeping strings and orchestral flourishes that transport listeners to another century.

It’s theatrical without being over-the-top, matching the literary weight of lyrics about auroras and unnamed women.

This song represents Taylor at her most vulnerable about fame’s toll, wrapped in gorgeous imagery that makes isolation sound almost appealing.

While Folklore earned massive praise, this delicate closer often gets overlooked despite being one of the album’s most romantic and poetic moments.

3. So High School (2024)

From The Tortured Poets Department: The Anthology comes this surprisingly lighthearted gem that catches you off guard.

After an album full of heavy emotions, So High School bounces in with playful energy and knowing smiles.

Taylor channels teenage romance through an adult lens, finding humor and sweetness in feeling young again.

The production keeps things breezy and fun, proving she hasn’t lost her ability to write infectious pop hooks.

What’s clever here is the self-awareness—she’s not actually in high school anymore, but love can make anyone feel like a giddy teenager again.

It’s a palate cleanser that shows emotional depth doesn’t always require darkness, and sometimes joy deserves its own spotlight too.

4. Dorothea (2020)

Tucked into Evermore, this track feels like flipping through an old yearbook and wondering about the person who got away.

Taylor addresses someone who left their small town for bigger dreams, and you can hear both pride and longing in every word.

The indie-folk production stays warm and intimate, like a conversation over coffee in a familiar diner.

She never judges Dorothea for leaving, instead celebrating her courage while keeping the door open for return.

It’s a masterclass in perspective—the narrator stayed behind but doesn’t sound bitter, just genuinely curious and caring.

This song captures small-town dynamics perfectly, where everyone watches each other grow up and apart, hoping someday paths might cross again.

5. Invisible String (2020)

Folklore’s most hopeful moment arrives with this belief in cosmic timing and meant-to-be connections.

Taylor looks back at past heartbreaks and realizes they were necessary steps leading to her current happiness.

The metaphor of an invisible string tying two people together across time and space feels both whimsical and profound.

She mentions specific colors and places, grounding magical thinking in concrete memories that make the concept feel real.

Unlike her earlier romantic songs that focused on intensity or drama, this one celebrates quiet certainty and gratitude.

It’s grown-up love that appreciates the journey instead of just the destination, wrapped in acoustic gentleness that matches its tender message perfectly.

6. Right Where You Left Me (2020)

Did you know this Evermore bonus track might contain Taylor’s most devastating single image?

She pictures herself frozen in a restaurant corner, unable to move forward while the world spins on around her.

The lyrics paint such a specific scene—friends getting married, strangers living lives, while the narrator remains stuck in the exact moment heartbreak arrived.

It’s haunting how she describes feeling like a museum piece that people pass without really seeing.

What makes this absolutely gutting is the self-awareness throughout.

She knows she’s stuck, knows it’s been too long, but can’t figure out how to unfreeze herself and rejoin life’s forward motion.

7. Treacherous (2012)

Red contains so many emotional gut-punches that this slow-burning masterpiece often gets overshadowed by louder neighbors.

Treacherous builds from whispered confession to full-throated declaration, mirroring the dangerous attraction it describes.

The production choices are brilliant—starting minimal and vulnerable before drums and guitars crash in like falling off a cliff.

Taylor’s voice conveys both fear and excitement about loving someone she knows might hurt her.

Two words repeated throughout—”this slope is treacherous”—capture that specific feeling when your brain screams warnings but your heart refuses to listen.

It’s mature songwriting that acknowledges risk while choosing passion anyway, making it one of her most emotionally intelligent early tracks.

8. Cowboy Like Me (2020)

Evermore’s moodiest moment tells the story of two con artists recognizing each other across a crowded room.

The Old Hollywood production and noir imagery create something that sounds like it belongs in a classic Western film.

What’s fascinating is how Taylor positions both characters as equally guilty—neither judges the other for their past schemes.

They’re kindred spirits who’ve been running similar games, finally meeting their match.

The phrase “forever is the sweetest con” flips romantic language on its head, suggesting even their genuine connection might be another hustle.

It’s cynical and romantic simultaneously, proving Taylor can write complicated adult relationships with nuance that goes beyond simple good-versus-bad dynamics.

9. Clean (2014)

Closing 1989 with atmospheric restraint instead of pop explosion was a bold choice that paid off beautifully.

Clean uses rain and drought metaphors to describe finally moving past heartbreak into genuine healing.

The production stays deliberately understated, with Imogen Heap’s influence creating spacious soundscapes that let emotions breathe.

It’s not about triumphant revenge or finding someone new—it’s about becoming whole again independently.

Ten months sober, Taylor sings, comparing heartbreak recovery to addiction recovery in ways that feel profound rather than dramatic.

This track proves she understood even then that true strength comes from internal peace, not external validation or rebound relationships.

10. Happiness (2020)

Evermore’s most mature meditation on love’s ending acknowledges something rarely discussed in breakup songs—that both people can be good and still wrong for each other.

There’s no villain here, just incompatibility and grief.

Taylor’s vocals carry exhaustion mixed with acceptance, perfectly matching lyrics about seeing happiness both in and beyond a relationship.

The production stays minimal, letting the emotional weight of words do the heavy lifting.

Lines about showing someone all their fears and later ruining their life cut deep because they’re honest about how love can transform into damage.

It’s grown-up heartbreak that refuses easy answers, making it one of her most emotionally intelligent compositions.

11. Holy Ground (2012)

While Red is famous for its angry anthems, this track takes the opposite approach—celebrating past love with genuine gratitude instead of bitterness.

The infectious drumbeat practically demands dancing, matching lyrics about remembering the good times.

What’s refreshing is Taylor’s perspective shift here.

She doesn’t pretend the relationship didn’t end or that it wasn’t painful, but she chooses to honor what was beautiful about it anyway.

The bridge builds to an emotional crescendo where she declares that night “holy ground,” elevating teenage romance to something sacred worth treasuring.

It’s a masterclass in healthy processing that shows maturity beyond her years at the time, wrapped in production that makes nostalgia feel celebratory rather than sad.

12. Mary’s Song (Oh My My My) (2006)

Imagine writing a song at sixteen that follows love from childhood through old age with such tenderness and wisdom.

Mary’s Song accomplishes exactly that, telling a complete life story in just over three minutes.

The narrative structure moves through decades—kids playing in the yard, teenage dating, marriage, grandchildren—with specific details that make it feel like a real family’s history.

Taylor’s voice carries innocence that matches the perspective perfectly.

What makes this truly special is its rarity in pop music: a love song about staying together forever that actually sounds believable.

It’s not dramatic or flashy, just sweetly honest about building a life with someone through ordinary moments that add up to everything.

13. I Know Places (2014)

1989’s darkest track pulses with paranoia and determination as Taylor describes protecting love from invasive outside forces.

The production feels urgent and slightly dangerous, matching lyrics about running and hiding from hunters with cameras.

She uses vivid imagery—loose lips sink ships, vultures circling, foxes hunting—to paint fame’s pressure on private relationships.

The chorus builds with stacked vocals that sound like multiple versions of herself offering sanctuary.

This song reveals the cost of celebrity that glossy magazine covers never show: constantly looking over your shoulder, unable to enjoy normal romantic moments without them becoming public property.

It’s both specific to her experience and universal for anyone who’s fought to keep something precious private.

14. This Is Me Trying (2020)

Folklore’s quietest confession might also be its most devastating.

Taylor strips away all defenses to admit she’s struggling, she’s trying, and sometimes that’s all she can offer right now.

The production stays deliberately minimal—soft piano, distant drums, echoing vocals that sound small and fragile.

She doesn’t ask for applause or validation, just acknowledgment that effort counts even when results don’t show.

Lines about pulling off the highway and pouring out her heart to strangers capture specific moments of crisis with painful clarity.

It’s the opposite of her triumphant anthems, instead offering solidarity to anyone who’s ever felt like they’re failing despite genuinely trying their best.

15. The Way I Loved You (2008)

Fearless contains this absolute firecracker that explodes with frustrated passion and confused longing.

Taylor contrasts a perfect, respectful boyfriend with the messy, chaotic ex she can’t forget, and the production matches that intensity perfectly.

The bridge builds to one of her most powerful vocal moments as she screams about missing screaming and fighting and kissing in the rain.

It’s raw teenage emotion that refuses to be rational or sensible.

What makes this track brilliant is its honesty about wanting drama even when you know stability is healthier.

She doesn’t resolve the conflict neatly, instead letting the emotional chaos speak for itself in ways that feel genuinely human rather than calculated.