Spill Your Guts In These Olivia Rodrigo Song-Inspired Outfits

“If I told you how much I think about her, you’d think I was in love!” These lyrics are from Olivia Rodrigo’s new single, “Obsessed,” but are also the perfect way to describe how I feel about the Grammy Award-winning artist. Last month, the superstar released five new tracks on her sophomore album GUTS. From the feel-good "So American" track that serves as Rodrigo's first optimistic love song to the melancholy “Scared of My Guitar” ballad that demonstrates the songwriter’s vulnerability, each of Rodrigo’s new songs has a distinct vibe and aesthetic, while all being true to the singer’s emo-angsty, hard-and-soft, ‘90s-tinged sound.

Inspired by these new tracks and ahead of my first Rodrigo concert, I curated an outfit guide for every GUTS song. As you scroll on, you’ll find outfits that are just as tongue-in-cheek as Rodrigo’s lyrics, as well as looks that mimic her ultra-stylized music video looks. If you want to channel your favorite GUTS song in your everyday wardrobe or need a last-minute concert outfit for Rodrigo’s upcoming 4-night Madison Square Garden shows, browse — and shop — below.

Many can relate to being put in a box by society, and Rodrigo gave us the anthem we needed to reclaim our power. To channel this song, consider a sweet ‘60s-inspired Peter Pan collar dress because you've got "class and integrity just like a goddamn Kennedy." Then flip the good girl script with not-so-school girl knee-high stockings and grungy Dr. Martens Mary Jane platforms. You can also pull from the “Coca-Cola bottles that I only use to curl my hair” lyric and buy yourself a kitschy soda can purse.

Ever thought about getting back with your ex? So has Rodrigo — if we are to believe her “Bad Idea Right?” story. Here, we found pieces nearly identical to the ones she wore in the music video, in which she leaves a house party to head to her ex’s apartment. Sure, you can always opt for a revenge dress, but we love the more unexpected pairing of a fuzzy cropped sweater with a sparkly sequin mini skirt like Rodrigo. To complete your look, throw on a red heart pendant necklace and classic Converse high-tops.

While Rodrigo wears a white strapless ruffle dress in her “Vampire” music video, we’re pulling inspiration from her 2024 Grammys performance gown instead. For a going-out outfit, opt for a crimson slip dress or a romantic lace maxi dress that any, erm, vampire would kill to wear. Add some gothic flair with a blood-stained pearl choker. Or, for a more casual outing, sport a vampire-inspired graphic tee that looks like it could be screaming along to Rodrigo’s lyrics, “Bleeding me dry like a goddamn vampire!”

Rather than taking on Rodrigo’s persona in her jealousy-drenched ballad, channel the angelic Lacy by pulling directly from the lyrics. “Eyes white as daisies” — opt for a yellow babydoll dress with dainty flower embellishments. “Like ribbons in your hair, I’m tangled all in knots” — cart up some hair bows (the 2024 “it” accessory that’s not going anywhere). “Skin like puff pastry” — a croissant-style ring works, right? “Like perfume that you wear, I linger all the time” — spritz on some unabashedly sweet perfume. 

To channel Rodrigo in this song about a homeschooled student trying to overcome feelings of social alienation, consider styling a modern, more mature version of a school uniform. That could mean pairing a cropped cardigan with a pleated mini skirt and Mary Jane flats. Or if this song evokes the feeling of wanting to crawl into a ball and stay at home, opt for a sweatsuit uniform of sorts in Rodrigo’s favorite color, purple.

No, this song isn’t literally about making a bed, but we’re going with that theme for an outfit option. Wear a luxe feather-trimmed pajama set to a club like Olivia and her “fair-weather friends.” But if the deeply saddening song has you wanting to stay indoors, cuddle up in a wearable blanket (similar to Rodrigo’s must-have weighted blanket), heart-printed boxers, and cuddly slippers (these ones are an R29-reader favorite style). 

As Rodrigo puts it, “Love is never logical.” With themes of confrontation, gaslighting, and heartbreak, your outfit should match the heart-versus-mind energy. And what’s better than a cheeky graphic T-shirt and a pair of cozy sweatpants to sulk in? Keep with this song’s message and cart up a heart- and brain-printed pendant to add to your favorite necklace chain. Then upgrade your Converse game with a Comme des Garçons collab sneaker that fittingly features the luxury brand’s heart logo.

Rodrigo loves wordplay, from her interpretation of “guts” (feeling gutsy, spilling your guts, hating your guts, etc.) to her single “Get Him Back!” Sure, she wants to get her ex back… but only to make him suffer like she did. Copy her music video look and throw on a white baby tee, floral mini skirt, and black platform boots for a soft-meets-hard outfit. And while we don’t condone violence, you can also take inspo from the lyric “I wanna kiss his face with an uppercut,” and slip on a brass knuckle-inspired ring. 

Wear your heart on your sleeve (literally) with a bold cut-out denim jacket to match the energy of this banger. If the line “I’m planning out my wedding with some guy I’m never marrying” sticks with you, perhaps you need a white mini dress. Pull casual bridal dresses from Revelry or Abercrombie’s new Wedding Shop. Then make your look a bit edgier (and less bridal) with Rodrigo’s signature fishnet tights.

If “The Grudge” is your cry-in-the-car song, welcome to the club. It has a combo of anger and betrayal and a blend of toughness and sadness. Replicate that juxtaposition with an outfit that plays with contrasting textures. Pair a sheer, romantic lace top with an edgy leather pant, or better yet, find yourself an asymmetric dress that combines black lace, satin, and velvet. And rather than holding your undying love like a grudge like Rodrigo, hold a celebrity-approved purse that’s too small to possibly hold all your heavy baggage in.

Do you also picture a sad pageant queen or Molly Ringwald's insecure Sixteen Candles character when listening to “Pretty Isn’t Pretty”? Struggling with her appearance and attempting to cover up her insecurities, Rodrigo discusses covering up her face with makeup. But rather than covering up, accentuate your beauty with a playful lip and cheek tint. Keeping with the Sixteen Candles vibes, consider slipping into a pink puff-sleeve mini dress that’s more modern than Samatha’s pink, poofy bridesmaid and prom dresses.

In “Teenage Dream,” Rodrigo, now 21, sings about her final year as a “teen.” We put together a birthday-appropriate outfit consisting of a denim dress, a personalized necklace that can be customized with your age or birth year, and a friendship bracelet. If you want to be on the nose, you can also wear a Katy Perry “Teenage Dream” album cover-inspired T-shirt. 

Never afraid of screaming out all the dark, embarrassing things we’ve all thought before, Rodrigo sings about comparing herself to her boyfriend’s ex-girlfriend. If you want an edgy outfit that mimics the music video’s costume, wear a black tulle dress paired with a heart-pendant choker, red crew socks, and chunky Mary Janes. But if instead you’re feeling like the ex-girlfriend that’s being obsessed over, cart up a kitschy “World’s Best Ex Girlfriend” baby tee that Rodrigo would definitely wear herself.

Feeling misunderstood? But also proud of your true self? Then this bop is likely your favorite new GUTS song. A tough cookie deserves a badass outfit to match their personality, and we think a retro-style boiler suit is the way to go. Balance it out with cat-eye sunglasses and a leather jacket. This song showcases Rodrigo’s twang and country vibe, so we suggest getting an interesting pair of cowboy boots to match.

Soft, delicate, and vulnerable, this song has a quietness that makes us conjure up a visual of Rodrigo strumming her guitar while wearing a sweet floral dress and warm-weather accessories like a crochet bandana or cap and sandals. If you don’t play the guitar, you could wear a guitar pick necklace that represents your love of music (and this song).

“Stranger” evokes the feeling of the weight of a past love coming off your chest, the realization that all your pain has made you stronger, and the hopefulness of a new beginning. Now, that’s pretty difficult to translate into an outfit, so we pulled from Rodrigo’s storytelling of waking up in bed to all of these feelings and reflecting on her past relationship over a cup of coffee. For this, you’ll want to throw your hair up in a messy bun while wearing a matching pajama set, dramatic floor-length robe, and comfy slippers.

We know and love Rodrigo for her relatable heartbreak bops, but the singer just released her first true love song in which she sounds happy and optimistic about her love life. Many have inferred that she’s singing about her current boyfriend, British actor Louis Partridge: “He says I'm so American.” For a literal interpretation, wear an American flag sweater, OG Americana Levi’s jeans, retro-inspired sneakers, and a belt bag.