Songs for Sweater Weather

So it’s my favorite time of year and that would be the fall. Yes, Autumn. The best season of the year. Hands down. I am not a summer guy. Never have been. I hate the summer. I despise hot weather. I hate it when it’s humid and muggy, and here in Chicago, we get slammed with humidity and ridiculous heat all summer long.

Those dog days of August? Pure misery. This past year was even worse, with multiple 90+ degree days that sucked the life right out of me. By the end of summer, I feel like I’ve been cooked.

But now, September rolls around, the air cools off, and suddenly everything is glorious. Sweater weather, baby.

I’ve always loved fall, even when I was a kid and had to go back to school. Didn’t matter. I still loved pulling on a sweater, hearing the crunch of leaves under my shoes, feeling that little chill in the air.

And yes, shout-out to the legendary Bronx Beat sketch on Saturday Night Live with Maya Rudolph and Amy Poehler. “Sweater Weather!” That’s the catchphrase, and that’s exactly what fall is all about.

Everything about autumn is perfect: the leaves changing color, the crisp smell in the air, caramel apples, pumpkins, hayrides, Halloween (by far, my favorite holiday), Thanksgiving right around the corner. The weather sweet spot is like 60 during the day and mid-40s at night.

That’s perfection. That’s the zone. I love seeing everyone bundled in sweaters and jackets. I love that sense of brisk energy in the air, the anticipation of the holidays.

And let’s not forget sports: the baseball postseason, the NFL kicking into high gear, the NHL season starting (hockey is my sport). It’s all happening in the fall. And of course, as a lifelong film critic, autumn is also movie season. 

The time of year when Hollywood gets serious. We leave behind the big dumb summer blockbusters and the garbage dump of August releases, and then September through December is packed with the important, awards-worthy films.

Fall festivals like Toronto and Venice happen, Oscar buzz starts, and you know you’re going to see some of the year’s best movies. So between the weather, the holidays, the sports, and the movies? Fall wins. Every year.

And the music... oh, the music. That’s where this list comes in.

Because autumn has a sound. You know what I mean? There are songs that feel like fall. Sometimes the lyrics are explicitly about the season. Sometimes it’s the tone, the mood, the instrumentation.

It is something that makes you think of leaves crunching, gray skies, brisk air, and sweater weather. Some of these songs are obvious, others are just ones that I personally connect to this time of year.

So I’ve put together 15 songs that I think are perfect for autumn. No ranking here, just songs that, for me, capture the spirit of fall. Different artists, different genres, but all with that autumn-like feel.

And yes, the last three are by Dave Matthews Band, because Dave is one of my favorite artists of all time and so many of his songs are about mood, about capturing a feeling.

Dave has three songs in particular that just scream fall to me, and they had to be on this list.

So here they are: 15 fantastic songs to soundtrack the best season of the year. Click on the videos, listen to the music, and let yourself sink into sweater weather.

15 SONGS FOR SWEATER WEATHER:

1. Where You Lead – Carole King

A Carole King classic from her legendary Tapestry album. Warm, soulful, and comforting, it's the perfect way to ease into autumn. It’s also the theme song to one of the coziest TV shows ever made: Gilmore Girls.

I love Gilmore Girls. Always have. Always will. It’s one of my comfort shows. Lorelai, Rory, Luke, the quirky small-town weirdos of Stars Hollow... I could live there. And when Carole King’s voice comes on with this song? Instant sweater weather.

2. Landslide – Fleetwood Mac

One of Stevie Nicks’ most beautiful songs, full of reflection, change, and the passage of time. The lyrics about mountains, children, and getting older feel like autumn itself, bittersweet and gorgeous.

This is one of those songs that stops you in your tracks. You hear the first chords and you’re done. It’s melancholy in the best way, and if you’re walking through fallen leaves when this comes on? Forget it, that’s an autumn movie montage right there.

3. Cardigan – Taylor Swift

From Folklore, her soft, introspective, woodsy pandemic album. The whole record feels like fall, but Cardigan especially captures the vibe of chilly nights, layered sweaters, and longing.

Say what you want about Taylor, but she nailed the fall aesthetic with Folklore. This song feels like it was written specifically for when the temperature dips below 55 and you pull on your favorite sweater. Yes, Taylor, it’s sweater weather.

4. Autumn Town Leaves – Iron & Wine

Sam Beam’s hushed vocals and delicate acoustic guitar make this a quintessential autumn song. It’s literally about leaves in an autumn town, and it’s as gentle and reflective as fall evenings get.

Iron & Wine is a unique, eccentric artist, who makes unique, eccentric music. This one sounds like the golden hour of an October afternoon when everything feels still and you don’t want the season to end.

5. Autumn Almanac – The Kinks

Ray Davies’ ode to everyday British life filtered through the crispness of autumn. It’s whimsical, quirky, and filled with imagery of leaves, tea, and cozy domesticity.

The Kinks don’t get nearly enough credit for being one of the most charming, clever bands of their time. This song is peak Kinks, weirdly specific, funny, and somehow universally relatable. Also, any song that celebrates autumn rituals is my jam.

6. September – Earth, Wind & Fire

The ultimate fall anthem. Funky, joyful, impossible not to dance to. “Do you remember the 21st night of September?” Of course you do. Everyone does.

My favorite autumn song of all time. Period. This song is September. It’s the soundtrack of fall parties, football games, and just being alive in crisp weather. If you don’t dance when this comes on, check your pulse.

7. Autumn Changes – Donna Summer

From her 1976 album Four Seasons of Love, this is Donna Summer in a disco groove, taking the changing of seasons and turning it into something lush and soulful.

Only Donna Summer could make autumn sound sexy. The orchestration is fantastic, and her voice is, as always, flawless. This is a fall jam for when you want your sweater weather to come with some glitter and a disco ball.

8. Harvest Moon – Neil Young

A gentle, romantic ballad about love lasting through the years, with the imagery of autumn nights and the harvest moon hanging over everything. A perfect campfire song.

I don’t care who you are, if you don’t get chills during “Because I’m still in love with you, I want to see you dance again” you might be dead inside. This is the kind of song that makes you want to slow dance in your driveway under a streetlight in October.

9. Leaves That Are Green – Simon & Garfunkel

From Sounds of Silence, it’s a simple, poetic song about the passage of time, love fading, and the inevitability of change. The falling leaves metaphor is as autumn as it gets.

Paul Simon could make reading a grocery list sound profound. This one is beautiful and sad in that uniquely autumn way. It’s the kind of song you listen to walking through a park when the leaves are crunching under your feet and you’re suddenly aware that you’re not 20 anymore.

10. Autumn in New York – Ella Fitzgerald & Louis Armstrong

A jazz standard, but Ella and Louis’s version is the definitive one. Warm, romantic, and dripping with nostalgia.

If I could teleport anywhere in the world during autumn, it would be New York City in the 1950s, listening to Ella and Louis sing this live. Pure magic. This is autumn in song form, and their voices together? Perfection.

11. Autumn Sweater – Yo La Tengo

A dreamy, indie-rock love song that captures longing, intimacy, and that quiet, moody vibe that comes with cooler weather.

Yo La Tengo is one of those bands that somehow makes every song sound like a memory. Autumn Sweater feels like being 25, broke, and in love in the city during fall. It’s melancholy, but in a comforting way.

12. October – U2

A short, hauntingly beautiful ballad from their 1981 album October. Simple piano, Bono in vulnerable mode, and lyrics that evoke change and mortality.

People always jump straight to The Joshua Tree or Achtung Baby, but October is underrated U2. The title track especially. It’s quiet, solemn, and it absolutely sounds like a crisp October morning when the world feels like it’s shifting.

13. Halloween – Dave Matthews Band

From Before These Crowded Streets, this is one of DMB’s darkest, angriest songs. Raw, emotional, and chaotic. A perfect fit for October.

This song is terrifying in a good way. Dave screams, the band pounds away, and it’s just pure catharsis. It doesn’t “sound like fall” in the cozy way, but it nails the darker, spookier side of the season. Halloween in song form.

14. The Last Stop – Dave Matthews Band

A complex, sprawling track blending rock, world music, and dark, apocalyptic lyrics. Not explicitly about autumn, but its heavy, dramatic mood fits perfectly with the season.

This one feels like late October when the leaves are almost gone and winter is looming. It’s heavy, it’s intense, and it’s brilliant musically. I always come back to it this time of year.

15. The Dreaming Tree – Dave Matthews Band

A haunting, beautiful epic from Before These Crowded Streets. It’s about memory, loss, and time slipping away, it's imagery that feels perfectly autumnal.

One of my all-time favorite DMB songs. It’s long, it’s moody, and it makes you feel like you’re sitting under a giant tree watching the leaves fall around you. Autumn in a single piece of music.

Closing Thought

So there you go: 15 songs that capture the spirit of autumn, sweater weather, and everything I love about this time of year.

Some are upbeat, some are sad, some are romantic, some are spooky. But all of them, in their own way, feel like fall.

Put on a sweater, grab a hot drink, step outside into the crisp air, and play these songs. Autumn is here, and it’s the best season of all.

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