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How Can I Shop My Boyfriend’s Closet and Look Like Carolyn Bessette in Love Story?

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Photo-Illustration: by The Cut; Photos: Allison Bornstein, Getty Images, Shuttestock

Dear Allison,

All of my parasocial crushes are dressing so well right now. I can’t get enough of Jacob Elordi’s Wuthering Heights press-tour looks, I loved Harry Styles’s blazer-and-jeans outfit at the Grammys, and I want everything Paul Anthony Kelly wears as JFK Jr. in Love Story. How can I incorporate the best menswear trends into my own wardrobe?

Sincerely,
A girl who shops in her boyfriend’s closet

Hi, fashion friend,

Wait, did you read my mind? Because Hollywood’s leading men are all over my mood board right now, and I love using their outfits as inspiration. Menswear can be intimidating. But if you take the time to break down each look, you’ll find so many styling nuggets to incorporate into your own wardrobe. It’s a treasure trove! Plus you don’t have to copy the look exactly; style inspiration can be more abstract than that. Just ask yourself what you like about the look and why it’s speaking to you, then build your own interpretation of it from there.

Let’s go through a few looks together.

Jacob Elordi in Chanel and Cartier jewelry at a photo call for Wuthering Heights

Photo: David Jon/Getty Images to Warner Bros. Pictures

Remember: Matching can be cool.

People are often scared of being too “matchy-matchy,” but this photo proves there is a way to do it right. From the black accents on the top, middle, and bottom, to the gold hardware, to the white cuffed sleeves that match the pants, the look is cohesive, intentional, and well thought out. Try it out next time you wear white and black by adding pops of both colors throughout the outfit from head to toe.

Roll up the sleeves of your cropped blazer.

I love the idea of a slightly cropped, boxy jacket. It’s a menswear-inspired silhouette that also happens to be very prevalent in womenswear these days— in fact, Elordi is technically wearing a womenswear jacket since Chanel famously does not make menswear. It’s a great choice for those who love menswear but are intimidated by the thought of actually shopping in the men’s section. Rolling up the blazer to show the white undershirt was also an excellent styling choice because it helps balance out the pants and makes the whole “matchy-matchy” vibe look intentional.

Embrace a cropped white jean year-round. 

I also really like these white jeans. His stylists, sisters Wendi and Nicole Ferreira, made them look appropriate for fall and winter by adding black shoes, a black belt, and a black undershirt. It gives the look nice balance and color symmetry. I love the length of them, too. If I were styling this look, I might have wrongly told the tailor to make the pants an inch longer, but I actually love the crop because it shows off his slim Celine loafers. Shoes that good deserve to be seen!

Paul Anthony Kelly as JFK Jr. in Love Story

Photo: FX

For being an ungodly handsome nepo baby, JFK Jr.’s style was always surprisingly functional, and the Love Story costumers have done a great job of capturing that. Most of his looks had a utilitarian factor I really respond to. Sure, he might’ve worn high-end designer pieces, but none of his clothes were stuffy or prim. He wore hats for warmth, comfortable sneakers when walking around the city, and rolled-up trousers when riding his bike. He was a New Yorker at the end of the day! If you’re watching the show, let it be a reminder that your style is a reflection of you and your life. It’s not a bad idea to think like a man when getting dressed: Prioritize ease, functionality, and practicality.

Harry Styles in Dior at the 2026 Grammy Awards

Photo: JC Olivera/WireImage

Wear a jacket as a going-out top. 

To me, this look is all about wearing a jacket as a going-out top. I love that there’s nothing underneath the jacket. I have a few collarless jackets and little blazers that I have put to the side because I’m not really wearing them right now. They feel a little grim. But wearing them with nothing underneath as a going-out top? That’s a whole new vibe! In my styling sessions, people are always asking me what to wear when you go out in your 30s. The answer is a jacket.

Go for the dainty shoe.

All of the internet boyfriends have been wearing tiny little shoes this year, and I’m into it. Both Elordi and Styles could have chosen heavier shoes to balance out their structured blazers, but I love that they both opted for dainty, slender flats. It’s whimsical and unexpected. It’s also comfortable and practical — great concepts to have on your mood board.

Colman Domingo carrying a Valentino Nellcôte tote on the streets of New York City

Photo: Jason Howard/Bauer-Griffin/GC Images

Swap your leather jacket for a leather bag. 

As millennials, we tend to rely on black leather jackets to give our looks some edge. But this photo proves that a black leather bag has the same effect. The look is so simple and kind of soft, but the bag adds a little hardness. Give your go-to leather jacket a break and try an oversize leather bag instead.

Let the accessories be the outfit.

This is such a simple jeans-and-tank look, but the thoughtful accessories make it inspo-worthy. I love how he incorporated a few different shades of brown in the shoes and the belt, even though the star of the show (the tote) is black. This is also a great example of mixing hardware. The chunky watch and the studs on the bag are silver, but the belt and chain are gold. If mixing hardware feels challenging to you, trying the technique with an otherwise simple outfit (like jeans and a white tee or tank) is a great place to start.

A$AP Rocky in Chanel on the cover of Esquire

Try layering with an extra-long shirt.

It feels counterintuitive for the bottom layer of an outfit to be longer than the top one, but Rocky is making it work. This entire look is so easy to re-create with pieces you already own: Tuck a T-shirt into your favorite pair of trousers, then layer on an extra-long button-up and your favorite blazer. Complete the look with — you guessed it — flat little shoes.

Saint Laurent men’s spring 2026 collection, looks 34 and 40

PARIS: Runway - Saint Laurent Menswear Fall/Winter 2026-2027, France - 27 Jan 2026
Saint Laurent - Runway - Paris Fashion Week - Menswear Fall/Winter 2026-2027
From left: Photo: Cyril Pecquenard/SIPA/ShutterstockPhoto: Victor VIRGILE/Gamma-Rapho via Getty Images
From top: Photo: Cyril Pecquenard/SIPA/ShutterstockPhoto: Victor VIRGILE/Gamma-Rapho via Getty Images

Style your printed scarf with a printed shirt.

Not photos of your celebrity crushes but still worth paying attention to! Both are expert examples of print-mixing — and you can easily re-create the look using a silk scarf. Instead of styling your striped scarf with the obvious choice, a solid-color shirt, try pairing it with a striped button-up. Make sure both pieces have similar color schemes and that the stripes are slightly different sizes.

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