Taylor Swift is perfect for a Sad Girl September playlist

NEW YORK, NEW YORK - NOVEMBER 12: Taylor Swift attends the "All Too Well" New York Premiere on November 12, 2021 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
NEW YORK, NEW YORK - NOVEMBER 12: Taylor Swift attends the "All Too Well" New York Premiere on November 12, 2021 in New York City. (Photo by Dimitrios Kambouris/Getty Images) /

The VMAs gave us many things, but none seemed to compare to Taylor Swift. She was iconic along with her huge announcement.

During the ceremony, Swift announced a new album was on the way and is set for release on October 13th. Entitled Midnights, the album seems like it’s going to be exactly what we’re all looking for.

After the ceremony, Swift also announced that there were going to be multiple different album covers for Midnights. While the original cover looks awesome, it’s not surprising that Taylor is giving us a lot of options. Each cover seems to embody a different emotion so no doubt the album is going to be intense.

Before the album comes out though, we’re all about celebrating Sad Girl September and what better than to listen to some Taylor Swift? That’s why it’s a Sad Girl September playlist full of Taylor Swift songs is the perfect way to kick off the month.

These Taylor Swift songs are the ultimate Sad Girl September anthems.

No surprise that we’re only going to be featuring songs from albums that Taylor owns. While that does limit the choices a bit, these songs are still definitely worth having on your playlist and we can still make a solid playlist with these albums.

Let’s start off strong with what is arguably Taylor Swift’s happiest album and that’s Lover. The album was released in 2019 and is frankly a love letter to love. That’s not to say there aren’t any sad girl September songs, though. For me, the two songs that are must-adds are definitely “Death by A Thousand Cuts” and “Cornelia Street.” Both songs have such a different vibe, but give the same message of longing for someone and wanting to be with them while knowing you can’t.

Heartbreak isn’t a huge theme of Lover but those two songs seem to embody something all of us have felt at one time or another. “Death by A Thousand Cuts” is definitely more upbeat but “Cornelia Street” feels like a punch in the gut which is why it’s the ideal choice for this list. While there weren’t many choices from Lover, those two songs really stand out to me as great picks for a Sad Girl September playlist.

Moving onto her new release, we have 2020’s Folklore. This album has such a melancholy feel and honestly feels like we’re reading Taylor’s journal. Even so, the obvious pick to add to your playlist is “August” as it’s both talking about the August ending and the end of the hope you had for a relationship. Listening to it, it sounds like such a beautiful song but it’s another sad song, full of longing and wanting something or someone you can’t have.

As for the second song from this album, this one was tough as a lot of them are frankly sad and are perfect for Sad Girl September. Even so, the song I chose was “Exile” which is Taylor Swift’s collaboration with Bon Iver. In a lot of ways, “Exile” feels like we’re actually listening to a couple break up and the aftermath of it which is heartbreaking in so many ways. Plus the lyrics are just so beautiful so how could you not want to listen to this one?

Moving onto Evermore, this album is a sister album to Folklore and once again, the sad vibes are there. In a way, this album feels a bit more melancholy and sad than any of Taylor’s previous projects. That’s why it was so hard to narrow it down to two songs, but “Champagne Problems” was the first song to come to mind.

The song, “Champagne Problems” tells a story about a woman having her own mental health struggles and not being able to see herself in a marriage because of it. It’s such a sad song but yet shows promise as the woman is able to reflect and see why it wouldn’t work. Plus it’s such a beautiful song so you’ll want to listen to it over and over again.

The other song is more of a wintery song but “Tis The Damn Season” has a similar vibe. This one is about going back home and running into your old flame. However, it’s that longing and wanting to be with them but knowing it’s essentially impossible. While the two don’t end up together in the end, it’ll make you want to reminisce and think which is why Taylor Swift is such a talented songwriter.

Moving onto Taylor’s re-recordings, the first song is one from the original version of Fearless and that’s “Breathe” featuring Colbie Caillat. While Fearless has a handful of songs related to heartbreak, “Breathe” amplifies that feeling. For those who don’t know, the song wasn’t written based on a romantic relationship but rather about losing a friendship which is something we all can relate to.

In a way, having to say goodbye to a best friend after they make a better decision isn’t always easy for the person they’re “leaving behind.” “Breathe” is a song that a lot of us can relate to no matter what age we are so it’s perfect for a Sad Girl September playlist.

As for the other song making the cut, I had to go with a song from Taylor’s vault and that’s “We Were Happy.” While this song is about a romantic relationship, it can be applied to other relationships, too. The song is basically about someone reminiscing on when you were happy in a relationship even though we all know the relationship didn’t work out. Even though you were happy in the relationship, it doesn’t guarantee everything works out.

Last but not least is Taylor’s latest re-recording and that’s her version Red. Red is such an iconic album for so many reasons which is another reason why it was hard to narrow down. The first one is frankly extremely underrated and that’s “I Almost Do.” This is another song where the person is reminiscing about the relationship and how they almost decide to call that person, but never end up doing it.

“I Almost Do” encapsulates that feeling of knowing someone intimately but not knowing them as you did before and grappling with that. There is so much longing and ideas of lost love within those lyrics and it gets me every time I hear it. Honestly, this one is definitely at the top of my Sad Girl September playlist tbh.

The final song making the cut had to be the 10-minute version of “All Too Well.” I’m sure this is on any Taylor Swift fan’s playlist so I don’t need to even explain this one but it had to make the list.

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Do you have a Sad Girl September playlist? Be sure to share your favorite Taylor Swift songs you’d add below.