The It-Girl’s Guide to Pairing Boots With Dresses This Fall

While we’re still mourning the loss of balmy summer days, we’re finding solace in the slew of scene-stealing boots carefully being added to our closets. Fall has upped its footwear game from seasons past, with sock, OTK, and slouch styles establishing themselves as essentials alongside classic stiletto and block-heel options. The only question that remains is which ones to slip into. Of course, the answer to this question lies largely in their styling potential. So, to help you settle on the perfect pair, we’ve tapped 10 trend-right Instababes to show you how to rock fall’s trendiest styles all season long.

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WALK WALK WALK 🔥

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1. Geometry Lessons: Take style cues from Alice, the better half of J’aime Tout Chez Toi, and amplify the modern effect of a vertically striped or geometric print dress with sculptural square-heeled ankle boots.

2. Color Theory: This Instababe had the right idea stepping out in dress + bomber + boots combo. But the real kicker is the way she works with color. The boots’ burgundy hue makes the jacket’s trim and frock’s floral detailing really pop. (Photo via whowhatwear)

3. Sock It to Ya: It’s hard denying the appeal of the sock boot — it’s likely the easiest stepper to pull off. Daintier than a block heel, it plays nicely with mini dresses and creates an element of drama when paired with voluminous silhouettes. (Photo via @collagevintage2)

4. Combat Contrast: Attention! The best way to add edge to a fanciful frock is to slip it on with a pair of don’t-mess combat boots and a leather jacket. Test drive the look with a ladylike maxi for an element of surprise — bet they didn’t see that one coming.

5. High Roller: Take your fall style to new heights à la Chriselle Lim by snagging a set of thigh-high boots. Equal parts dramatic and daring, they’re definitely not for the faint of heart. Mini dresses are the best way to show them off, but stick with long sleeves and classic or oversized silhouettes to keep the look from feeling too OTT. (Photo via chrisellelim)

6. Monochromatic Magic: Ready to push the sartorial envelope? Inject your ensemble with a double dose of color. Julia of Maffashion gives new meaning to millennial pink, matching her maxi to an equally as high-octane pair of velvet boots. (Photo via thestylestalkercom)

7. Hygge Approved: Boots can bring a healthy dose of sass to any OOTD, but they know how to hang with your comfiest threads too. Exhibit A: Kendall Kremer’s off-duty getup. Suede knee-high boots mirror the leisurely vibe of the cozy cardi while delivering just the right amount of urban sophistication. (Photo via styledsnapshots)

8. Do Slouch: Slouchy boots are arguably the biggest trend of the season. And while you could easily wear them over skinny jeans or alongside a suede mini skirt, if street style cred is what you’re after, then rock ’em with a bold midi dress — the brighter, the better. (Photo via chloechill)

9. Statement Stompers: If elevated minimalism is more your style, lug-soled knee-highs are most definitely the way to go. Play with clean lines and large-and-in-charge accessories to nail an Instaworthy look. (Photo via zinafashionvibe)

10. Pattern Play: It’s all in the details. Look to patterned, embroidered, or embellished boots to weave an element of intrigue into an all-black or monochromatic ensemble. (Photo via offwhite.swan)

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Slingback shoes are wonderfully versatile – you can easily wear them as awedding guest or to an elevated happy hour with the girls! Though they’re a bit less practical than your average walking sandals, they’re perfect for looking trendy and on-point. This underrated shoe silhouette is quickly coming to light, so make sure you pick up a pair before you spot ‘em on all the cool fashion people.

Naturalizer Jayla Low Heel Slingback Pumps

Naturalizer makes such comfy shoes, and these slingback pumps are no exception! They're made of leather, so you can be sure they'll hold up to years of walking and wear. The square toe and chunky heel give them a very approachable feel, which you can style casually or for more formal occasions. They're crafted with responsive cushioning on the soles for shock absorption and impact protection – which essentially makes walking worlds easier for all-day comfort.

The Naturalizer Jayla Low Heel Slingback Pumps are shoppable in 5 other colors for $110 on Amazon.

Youngshow Comfort Slingback Pumps

You don't have to mess with a single buckle with these slingback shoes. The wide heel on them means no missteps, trips, or slips – just downright comfort. The woven upper material is soft and stretchy, plus it's available in tens of different colors and styles. We adore this one because of the contrasting toe color. It makes for a playful outfit addition!

The Youngshow Comfort Slingback Pumps go for just $27 on Amazon.

Coutgo Slingback Kitten Heels

The sophisticated woven faux buckle detail on these heels is everything. Crafted with leather on the outside and a soft padded foot bed on the inside, you'll enjoy wearing these short, concave kitten heels just as much as you like looking at them. These slingback shoes can work with any ensemble – from jeans, dresses, shorts, and skirts, they'll give your look an added air of luxury.

The Coutgo Slingback Kitten Heels come in several other colors and are shoppable for $50 on Amazon.

Steve Madden Graya Slingback Pointy Toe Flats

For some edgier footwear, these slingbacks bound in silver hardware are the way to go. If you find yourself reaching for your Doc Martens more than your Nike sneaks, these flat-footed shoes will be an instant fit in your wardrobe. The two wide straps on top are adjustable by buckle to suit your step.

The Steve Madden Graya Slingback Pointy Toe Flats come in 3 other colors and are shoppable for $120 at Nordstrom.

Franco Sarto Racer Slingbacks

Make like cool girl Brie Larson and rock some butter yellowshoes for summer! They're your one-way ticket to looking uber-trendy for the season, plus you can wear them in so many different contexts. These Franco Sarto shoes are made from partially recycled materials, but give off a smooth leather effect. More than anything, the dramatic pointed toe will take your look to the next level. The heels measure about 2 inches, so you won't have too hard a time stepping out in these slingback shoes.

The Franco Sarto Racer Slingbacks come in 5 other colors for $115.

Jeffrey Campbell Rayna Slingback Heels

These are not your average slingback shoes! They boast a very sleek, but very chic shape that's finished off nicely with a slim kitten heel. Each shiny patent leather shoe is as strappy as can be, with 5 different adjustable straps sprawling on top of the foot. They secure on the side with small silver buckles, too.

The Jeffrey Campbell Rayna Slingback Heels are $178 at Free People and come in two other colors and fabrications.

Genshuo Low Kitten Heel Slingbacks

Metallic shoes are huge right now, so you'll be perfectly on-trend when you snag these slingbacks. Comfort is at the core of these patent leather and faux suede cuties – there's a soft padded insole and the outsole is made from wear-resistant rubber for an easy strut.

The Genshuo Low Kitten Heel Slingbacks come in 10 other colors for $40 on Amazon.

Bibi Lou Suzy Slingback Heels

These shoes are like a hybrid between ballet flats and slingbacks. And they're perfect. The toes are giving more ballet flats, while the heels feel especially kitten heel. You'll enjoy the coverage at the toes with an adorable square toe and cutesy bow tie, but appreciate the comfort levels even more, as the heel measures only 2 inches high.

The Bibi Lou Suzy Slingback Heels also come in black for $160.

Chinese Laundry Rozie Denim Slingbacks

These slingbacks easily let you live out your Barbie dreams, all while looking super stylish! The bright pink color (made from a denim material) just screams summertime, and you'll def be toting around in these all season long, thanks to their cozy fit. The block heel is easy to step in, plus the back strap is rid of all buckles or clasps for easy on and off!

The Chinese Laundry Rozie Denim Slingbacks also come in blue for $70.

Franco Sarto Khloe Slingback Pumps

If you wanna feel like the main character (you already are, but you might as well dress the part!), these red-hot heels are *the* slingback shoes for your vibe. The harsh pointed toe tells everyone that you are that girl. The thin, Mary Janes-esque top strap is adjustable with an elegant gold buckle, but the back strap is simply elastic so you can put 'em on with ease.

The Franco Sarto Khloe Slingback Pumps come in 5 other eye-catching colors for $125.

Jeffrey Campbell Striper Slingback Heels

Dare to be bold with these silver metallic slingbacks clad in woven details! The thin straps feel extra elegant, while the dramatic toe point is more experimental. For those looking to expand their footwear lineup, these kitten heels will be with you everywhere you go this summer.

The Jeffrey Campbell Striper Slingback Heels also come in a nude colorway for $185.

Sam Edelman Terra Slingback Block Heels

These brown beauties feel like the ultimate office shoe. They'll give your workwear an instant lift with a trendy squared toe and classic slingback straps. The block heel doesn't limit your walking at all, either! This style also comes in black, white, and silver metallic colors.

The Sam Edelman Terra Slingback Block Heels are currently on sale for $105 (was $140).

Vagabond Hennie Sandals

These high-coverage sandals from Vagabond have a chunkier feel, great for those who get a good amount of steps in, but still want to look chic. The 90's-inspired top half of these shoes is made from leather, with a small area for open toes. The ankle strap is adjustable by a small silver buckle.

The Vagabond Hennie Sandals are $150.

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We are now two for two on expecting Taylor Swift to announce Reputation (Taylor's Version) during an acceptance speech and getting an album announcement instead. After showing up to the 2022 VMAs in a "Look What You Made Me Do"-inspired outfit and announcing Midnights, Taylor Swift wore a black and white ensemble on the 2024 Grammys red carpet before telling the world her new album The Tortured Poets Department is coming this spring! Here's everything we know about the new Taylor Swift album. (Here's everything you need to know about Taylor Swift (Taylor's Version) too ;)).

What is Taylor Swift's The Tortured Poets Department?

Image via Taylor Swift/Instagram

Taylor Swift's new album (which is also referred to as TS11) is called The Tortured Poets Department. Taylor Swift announced the album while accepting the award for Best Pop Album at the 2024 Grammys. While we don't know the exact vibe of the album, over the last year, we've gotten quite a few clues about what we can expect! Just like "Daylight" at the end of Lover sets up Midnights, I think "Dear Reader" sets up The Tortured Poets Department.

Taylor's official announcement features beautiful language that evokes the same emotion "The Lakes" does, which makes me believe TTPD will be similar to Folklore and Evermore (maybe it'll even serve as the third sister album Swifties thought we'd get in 2021?). Some fans are also convinced TTPD connects to Reputation, and TBH, I'm hopping on this train!

"I think the two albums are sisters albums, but in like an opposite way," one Reddit user says. "Reputation is all black, this one is going to be all white and softly coded."

"Reputation is presented as a dark album but is truly a love album," another user comments. "This one is presented as soft and white but I bet the lyrics will be devastating."

I'm expecting TS11 to have the same lyrical prowess as songs like "Would've, Should've, Could've," The National's "The Alcott" (on which Taylor's a featured artist), and "You're Losing Me." Taylor is all about looking past appearances and telling a complex story, and The Tortured Poets Department will be no different. Just like Reputation is an edgy, glittery, emotionally-charged version of the beginning of her relationship with ex-boyfriend Joe Alwyn, I totally agree that TTPD could look grounded, airbrushed, and dreamy from the outside, but the lyrics will be SAD.

There's also been some discussion that TS11 could be another pop album that's even more nuanced than Midnights. Well, during her Eras Tour show in Sydney, Australia she played yet another round of suspicious surprise songs. While sitting at the piano, Taylor Swift takes her earpiece out and calls attention to the keyboard. "Do you hear that?" she says (via TikTok). "My damn keyboard's playing a synth sound." She then does what she almost always does when dropping an Easter egg: she smirks.

"That sound is how the album starts, mark my words," one comment reads. Another says, "That smirk tells me everything I need to know."

When is The Tortured Poets Department release date?

Image via Neilson Barnard/Getty Images for The Recording Academy

The Tortured Poets Department is dropping April 19, 2024. But on February 16, an artist by the name of Nils Sjöberg posted a song titled "The Tortured Poets Department." You might be wondering, "Why is this noteworthy? Who's Nils?" Nils Sjöberg is the pseudonym Taylor Swift has been using for over 10 years! With the fake name, she's written hits like "This Is What You Came For" by Rihanna, so when the title track of TS11 popped up on Spotify, it didn't take long for Swifties to notice.

The singer's voice sounds like it could be an auto-tuned version of Taylor's, but admittedly, it could also be AI. With the recent advancements in audio AI, some tracks from The Tortured Poets Department have supposedly leaked online, but we'll have to wait until April 19th to hear what the album *actually* sounds like. Either way, Nils' song is a fun one to listen to!

At the Eras Tour shows in Tokyo, Taylor Swift explained when she started working on TTPD. “I’ve been working on Tortured Poets since right after I turned in Midnights,” she said onstage. “So, you turn in an album months in advance…and I’ve been working on it for about two years. I kept working on it throughout the U.S. tour and when it was perfect, in my opinion, when it was good enough for you, I finished it.”

"Soon you'll get to hear it, soon we'll get to experience it together," she continued. "I'm over the moon about the fact that you guys care about my music...Everyone’s like, ‘Why do you make so many albums?’ And I’m like, ‘Man, because I love it! I love it so much! I’m having fun, leave me alone.'”

The brand new album follows Speak Now (Taylor's Version) and 1989 (Taylor's Version). When Midnights was announced after Fearless (Taylor's Version) and Red (Taylor's Version), I wondered whether she'd have a two rerecordings, one new album pattern and it looks like that's what we're getting!

How do I presave The Tortured Poets Department?

Image via Taylor Swift's official store/UMG

Before The Tortured Poets Department's release on at midnight on April 19 (we're less than a month away!), go ahead and pre-save it. It'll make streaming the album a little bit easier because when you pre-save, the album will pop up for you as soon as it drops! Go to Taylor Swift's official website and click on the "Pre-add/Pre-save" button. It'll take you to a new page where you can save it on Spotify or Apple Music (depending on which service you use), and you can also pre-order at stores like Target!

How many songs will be on The Tortured Poets Department?

Image via Taylor Swift/Instagram

Taylor Swift dropped The Tortured Poets Department song list February 5, and we already have theories about what each track could reference. IMO, "I Can Do It With A Broken Heart" is totally referencing Taylor Swift's performances of "Lover" following her split from Joe Alwyn (you can see her crying during the set), while there's a good chance "Florida!!!" is referencing her first Tampa concert, which was the first show she performed after the breakup became public knowledge. Taylor Swift's dad Scott Swift recently told fans he's most excited for Swifties to hear the title track and "Florida!!!" Here's the full tracklist for TS11:

  1. Fortnight (feat. Post Malone)
  2. The Tortured Poets Department
  3. My Boy Only Breaks His Favorite Toys
  4. Down Bad
  5. So Long, London
  6. But Daddy I Love Him
  7. Fresh Out the Slammer
  8. Florida!!! (feat. Florence + The Machine)
  9. Guilty as Sin?
  10. Who's Afraid of Little Old Me?
  11. I Can Fix Him (No Really I Can)
  12. loml
  13. I Can Do It With A Broken Heart
  14. The Smallest Man Who Ever Lived
  15. The Alchemy
  16. Clara Bow
  17. Bonus Track: The Manuscript
  18. Bonus Track: The Bolter
  19. Bonus Track: The Albatross
  20. Bonus Track: The Black Dog

Will The Tortured Poets Department be explicit?

Image via Taylor Swift/Instagram

There are 7 explicit songs on The Tortured Poets Department: "The Tortured Poets Department," "Down Bad," "But Daddy I Love Him," "Florida!!! (feat. Florence + The Machine)," "loml," "I Can Do It With A Broken Heart," and "The Smallest Man Who Ever Lived."

What is the theory of Taylor Swift's double album?

Image via Matt Winkelmeyer/Getty Images

Throughout her stay in Sydney, Australia for the Eras Tour, Taylor Swift has been dropping lots — and I mean lots — of twos. @v_swiftie_ points out that in addition to holding up the number two while announcing The Tortured Poets Department, she's been playing more surprise song mashups than normal, and Taylor Nation has been posting Instagram stories featuring the number 2 instead of the number 13. Suspicious, Tay, very suspicious.

What is The Albatross about?

Image via Taylor Swift/Instagram

During one of her Eras Tour shows in Sydney, Australia, Taylor Swift announced a new version of The Tortured Poets Department featuring exclusive bonus track "The Albatross." This new album already has some crazy track titles — all with pretty noteworthy meanings.

According to Collins Dictionary, if you call someone an Albatross, "they cause you great problems from which you cannot escape, or they prevent you from doing what you want to do," while a Bolter could refer to someone bolting out of a relationship (or bolting from a restaurant to a car like in this viral clip 🤨).

Meanwhile "The Alchemy" refers to the continual process of trying to turn something into gold — remember how Taylor Swift spent 6 years saying her relationship with Joe Alwyn was golden? Buckle up Swifties, TS11 is going to be a wild ride.

What does loml mean?

Image via Taylor Swift/Instagram

At first glance, the twelfth song on The Tortured Poets Department, "loml," means "love of my life." Some fans were wondering if the song was a nod to Harry Styles since his Harry's House finale track is "Love of My Life" (the album also features a track named "Daylight" which is another funny connection to Taylor Swift). But Bonnie & Emily from ChatsAndReacts have got me thinking about the track in a whole new way.

Emily says that while Taylor might sing about the love of her life at the beginning of the song, she also has the potential to switch it up each verse. "Lie of my life" and "loss of my life" are HEART WRENCHING, and totally something Taylor would write.

Will The Tortured Poets Department have any featured artists?

Image via Frazer Harrison/Getty Images

Yes, The Tortured Poets Department will feature Florence + The Machine on the song "Florida!!!" and Post Malone on the song "Fortnight." And after Taylor Swift teased a variety of collaborations by posting handwritten lyrics from artists like Harry Styles and Lorde, Swifties are wondering if The Tortured Poets Department will be the "collab album" we never got.

Another clue that leads me to believe this is true is the fact that the title of this album is so much longer than her other titles — and she refers to herself as "Chairman" of the department. Who are all the constituents?! Are they all the same artists who left Scooter Braun's management last year? Only time will tell, because as far as I'm concerned, surprises aren't out of the question until the TS11 era is over!👀

How can I buy The Tortured Poets Department?

Image via Taylor Swift store

You can pre-order a bunch of different versions of The Tortured Poets Department on Taylor Swift's website right now, includingThe Tortured Poets Department CD + Bonus Track "The Manuscript", The Tortured Poets Department CD + Bonus Track "The Manuscript" andThe Tortured Poets Department Cassette + Bonus Track "The Manuscript".

What is a tortured poets department?

Image via Taylor Swift/Instagram

Taylor Swift has spent years talking about her anxiety, her sleepless nights, and her emotions. "My muses, acquired like bruises / My talismans and charms / The tick, tick, tick of love bombs / My veins of pitch black ink," she writes in her official Instagram post. "All's fair in love and poetry." My guess is that The Tortured Poets Department features a bunch of artists who all feel very deeply and have a similar ethereal, larger-than-life approach to their music.

As far as the name, it looks like The Tortured Poets Department could be referencing her ex-boyfriend Joe Alwyn's group chat name — "The Tortured Man Club" with Paul Mescal (who starred in Normal People while Joe starred Conversations With Friends. Both series are based on Sally Rooney books).

Are you excited for The Tortured Poets Department? What kinds of collabs or songs are you hoping for? Let us know in the comments and check out these Taylor Swift Disney Movie Posters Inspired By Her Songs for more fun content!

Lead image via Taylor Swift/Instagram

Personal style is personal for a reason. Whatever you wear is a complete reflection of who you are, and this is especially true for what shoes you slip into every day. Everyone’s got their go-to sandals, but sneakers are an entirely different game, I tell ya.

If your fave footwear brand is New Balance and you just so happen to be in the market for some squeaky-clean sneaks, I’ve basically done all the research for you to help you find your perfect pair. This list of the most popular New Balance sneakers details not only each style’s practicality, but their personality, too.

Ahead, find your perfect New Balance sneakers – based on your vibes!

New Balance 9060: The ‘Fit Flexer

If you just can’t resist dressing to the nines every single day, the New Balance 9060s will fit right into your fashionista flair.

These “proudly futuristic” New Balance sneakers deliver on Y2K aesthetics beyond compare. The wider base is reminiscent of Nike Shox – very tech-y and otherworldly. The upper part is made from mesh and suede, supplying a super elevated vibe.

The white and cream white coloration is so easy to pair with most every ‘fit. They’ll match with cargo pants, vintage jeans, or even mini skirts and denim shorts.

Reviewers of the New Balance 9060 are glad they invested in this $150 shoe because it's so versatile.

One reviewer toted the 9060’s for fitting into “all aspects” of their lifestyle. Another said that the arch supports “unreal,” so though they’re more fashion-forward than other New Balance kicks, they’re still uber-comfortable for a range of activities.

New Balance 990: The Thrift Shopper

The New Balance 990s are straight-up dad sneakers to the core, so if you gravitate towards the thrift store (or all things vintage-y), you’ll find that they go swimmingly with most outfits and will stand up to long thrift trips.

While they were originally manufactured for running (and they still are), the 990s scream streetwear to me. They appear more elevated than your average athletic running shoe, thanks to the smooth pigskin and fine mesh.

The inside is fitted with a bouncy FuelCell midsole cushioning, and the shoe is available in 4 different widths. The range!

The New Balance 990s are very similar to the New Balance 993s, which is less performance-based.

New Balance 574 Core: The Weekend Warrior

Whether you're hitting the club or the farmer’s market on the weekends, you want to be comfortable (I mean, who doesn't?). The New Balance 574 Cores are made for the weekend warriors.

New Balance describes this signature shoe as “uncomplicated, rugged, durable, and comfortable.”

Though the 574s are pretty basic, they’re earned themselves icon status. You’re sure to see at least one pair when you go out.

The outer layer is made from suede and mesh materials dotted with 100% recycled polyester details.

New Balance 550: The Sneakerhead

These New Balance sneakers aren’t just black and white. They’re “sea salt” with “gray matter” and “magnet.” So yeah, if you consider yourself overly particular about your sneakers, the New Balance 550s are the shoe for you.

These were revived from the late 80’s and early 90’s then re-released full-time in 2021, and they’ve been a modern fan-favorite ever since.

The flatter soles on these sneaks mean they’re not as practical for running or walking long distances, but since they have a history with basketball, you might be able to rock ‘em on the court. More than anything, they definitely give basketball vibes, which is perfect for any streetwear ensemble.

The mixed materials and chunky approach to the classic New Balance logo give these an unmistakable air.

According to New Balance, these best fit people with an average arch height. The thick sole and cushy ankle padding work the hardest to support your feet, rather than an arched insole.

New Balance 530: The Gym-Goer

The New Balance 530s are giving Erewhon baddie. They’re giving I drink smoothies for breakfast. They’re giving I live and breathe pilates.

The stark white colorway of these sneakers reminds me of the clean girl aesthetic, and they’re so pretty, you may have a hard time getting them dirty.

Though very stylish on the outside, it’s what’s on the inside that counts with the New Balance 530s. They’re fitted with an ample midsole section that cushions and compresses your step.

New Balance Fresh Foam: The 10K Steps A Day-er

For the more athletic among us (hello, hot girl walks!), the New Balance Fresh Foam sneakers are the way to go. They’re designed especially for walking and running, so you can count on them to be comfy.

They have an extra-soft cushioning for a cozy step, and every aspect of the footbed is intended to stabilize the foot.

This shoe especially supports walkers or runners with the tendency to step heel first, a bonus co-signed by the American Podiatric Medical Association – this pair received their Seal of Acceptance.

The upper part of the shoe is made of mesh, so it’s highly breathable, even on hot days. They’re great for high arches, too!

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Images via New Balance.

After confirming their breakup rumors were, in fact, only rumors, Justin and Hailey Bieber broke the internet on May 9 by announcing they're expecting! The couple has talked about wanting to start a family in the past, and I am so excited for this new chapter in their lives. Check out Hailey Bieber's pregnancy announcement — and the photos — below!

www.instagram.com

On May 9, the couple separately uploaded nearly identical Instagram posts of what looks like a vow renewal ceremony. In the photos, which overlook the mountains and feature a super cute rope swing, Hailey can be seen cradling her baby bump while wearing the most beautiful white lacy gown.

Hailey Bieber once promised GQ Hype that when she did get pregnant, the internet would be the last to know. "I want kids so bad but I get scared," Hailey Bieber also told The Sunday Times. "It's enough that people say things about my husband or my friends. I can't imagine having to confront people saying things about a child."

Image via Jon Kopaloff/Getty Images

TBH, Hailey Bieber's pregnancy just proves how in love Justin and Hailey are!! "words could never truly describe the beauty of who you are," Hailey captioned an Instagram post for Justin's 30th birthday. "love of my life, for life."

"YOU MAKE LIFE MAGIC," Justin Bieber said in his own Instagram caption. "OBSESSED WITH EVERYTHING ABOUT YOU. LOVE YOU BUM BUM."

I literally cannot get enough of this couple, and I can't wait to see what their growing family looks like over the next couple of years. Stay tuned for a gender and baby name reveal (should they choose to share) — this is going to be one cute kid!

Check back here for the latest news on Hailey Bieber's pregnancy!

Lead image via Jon Kopaloff/Getty Images

While it's always nice to see something realistic represented in our favorite TV shows, there are few things more painful than watching a TV breakup (especially when it reminds you of your own, oops!). Even when we don't actually know fictional characters IRL, it's absolutely devastating to see them break each other's hearts. (Although, I'll admit it's equally as bad as never seeing your favorite prospective couple get together — I'll never, ever forgive The 100 for what they did to Clarke and Bellamy!!).

Keep reading to see some of our most heartbreaking splits in recent television history — and then check outWhat Being Team Conrad Or Jeremiah Says About Your Dream TV Boyfriendto put a smile back on your face.

Brit + Co's Picks For The Worst TV Breakups

Image via The CW/WB

Rory and Jess from Gilmore Girls

This is one of my personal worst TV breakups because it seems like, out of all of Rory's boyfriends, Rory and Jess are going to stay together forever when they start dating. Not only does their love of books bring them closer together, but their personalities are so compatible — they're perfect for each other, IMO! But when Jess leaves for California at the end of season 3 (without saying anything to Rory, I might add) is unacceptable! They see each other a few more times over the course of the show, but it's never the same. This ending breaks my heart, and based on the final look he gives Rory during A Year in the Life, he also regrets it BIG TIME.

Image via NBC

Ross and Rachel from Friends

Friends is one of the most iconic sitcoms of all times, and Ross and Rachel is definitely one of the worst TV breakups. In season 3, this iconic couple decides to take a break, and in "The One with the Morning After," Ross wakes up with another woman named Chloe at the exact moment Rachel shows up at his door to get back together. Rachel finds out about the affair, and after a fight in Monica's living room, the couple calls it quits.

Regardless of how you feel about Ross using every opportunity to point out they "were on a break" when he slept with Chloe, seeing Rachel's reaction (and knowing the trust between them was broken) is one of the worst moments in the whole show. Just thinking about it makes my stomach bottom out!

Image via The CW/WB

Damon and Elena from The Vampire Diaries

This Vampire Diaries couple was truly endgame, and I can't lie: The will-they-won't-they of it all was one of my favorite things about the show. So when they broke up (to my horror), I was devastated.

Damon and Elena admit they're bad for each other in the season 5 episode "While You Were Sleeping" (then Damon tells her he doesn't even want to be friends. Ouch!!), but it's the season finale, "Home," that makes me extra emotional. When Damon gets stuck with Bonnie on the Other Side, he says goodbye to Elena, who's begging him not to leave but can neither see nor hear him. Say it with me: gut! wrenching!

Image via Erika Doss/Prime Video

Conrad and Belly from The Summer I Turned Pretty

The Summer I Turned Pretty fans are PASSIONATE about whether they're team Conrad or team Jeremiah (trick question, my OTP is Taylor and Stephen), and even the most dedicated Conrad stan hates the prom scene. You know, when he breaks up with Belly at her prom, in the rain. I know he just thinks Belly deserves better, but it's still very painful to watch. (Not quite as painful as him realizing Belly didn't know he loved her in episode 6).

Image via BBC/Prime Video

Fleabag and The Priest on Fleabag

In the history of TV, I don't think I've ever heard anything as heartbreaking as "I love you," "It'll pass." Like, who approved that line?! The viral moment comes at the end of the Fleabag series finale, when Fleabag is sitting with The Priest at the bus stop. Over the course of the series, we not only see how much these two care about each other, but how well they know each other (like how The Priest recognizes when Fleabag zones out). To be loved is to be known, and that's what makes this devastating TV breakup even more devastating.

Image via FOX

Schmidt and Cece from New Girl

When I hear "worst TV breakup" I IMMEDIATELY think of Schmidt and Cece from New Girl. Schmidt gets away with a lot of ridiculous things throughout this show, but dating two girls at one time is not one of them (nor should it be). After Nick has a hard time keeping Schmidt's love life secret, Schmidt finally comes clean to Cece in "Double Date," leaving both her and me in tears. No matter how many times you rewatch the show, it truly feels like their relationship (and maybe even the friend group) will never recover.

Image via HBO

Carrie and Aidan on Sex and the City

After so much back and forth, it's hard to accept Carrie and Aidan's final breakup on SATC. But in season 4's "Change of a Dress," Carrie realizes she's not ready for marriage and Aidan realizes he doesn't trust her after her affair with Big. The combo of broken trust and being at two different life stages makes this extra painful to watch, and I don't think any amount of rewatches (or And Just Like That binges) is going to change that.

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Lead image via Prime Video

This post has been updated.