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These Stylish Headphones Are a Sound Way to Upgrade Your Street Style
Plus, top headphone accessories to personalize your pair.
By Olivia Cigliano Plus Icon
Commerce Writer and Producer for Footwear News and WWD
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October 10, 2023, 9:13am
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In this article
- Apple AirPods Max Wireless Over-Ear Headphones
- Apple AirPods Pro 2nd Gen Headphones
- Apple EarPods Headphones
- Koss Porta Pro On-Ear Headphones
- Beats Studio Pro Wireless Headphones
- Sony WF-1000XM5 Earbuds
- Bose QuietComfort Wireless Headphones
- Beats Studio Buds +
- Marshall Major IV On-Ear Headphones
- Sennheiser Momentum 4 Wireless Headphones
- Bang & Olufsen Beoplay EX Wireless Earphones
- Master Dynamic MW75 Wireless Headphones
- Jabra Elite 8 Active True Wireless Earbuds
- Bowers & Wilkins Px8 Over-Ear Wireless Headphones
- Top Stylish Headphone Accessories
- Why Trust WWD
- Meet the Author
- Apple AirPods Max Wireless Over-Ear Headphones
- Apple AirPods Pro 2nd Gen Headphones
- Apple EarPods Headphones
- Koss Porta Pro On-Ear Headphones
View More
Keys, wallet, headphones — it’s the modern commuter’s checklist before running out the door. Stylish headphones are as consistent in a day’s uniform as an everyday bag or carry-all tote and have quickly taken on a certain model-off-duty panache. Over the decades, headphones evolved from clunky headgear to minimal wired buds and barely-there bluetooth pods, and all of the above are worn as style accessories today. Whichever sonic style you choose, headphones have transcended mere function to communicate personality through tech, and are versatile enough to polish off any look, from an elevated ensemble to an airport-chic sweatsuit.
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Apple’s AirPods Max headphones are one of the most prominent pairs seen on street style stars and celebs. The burnished, boxy headphones have been styled by every fashion force that’s in-the-know, including Bella Hadid, Timothée Chalamet, Sarah Jessica Parker, Dua Lipa, Hailey Bieber, Ariana Grande, Chiara Ferragni — the list goes on. The fixation has inspired a new category of accessorizing, as myriad contemporary designs have flooded the market since AirPods Max’s December 2020 launch. Vintage-inspired tech has also flung to the forefront in a new context. See: The fashionable comeback of Apple’s wired EarPods or retro aesthetics iterations from Beats and Koss.
A New York Fashion Week guest seen wears AirPod Max headphones in September 2022. (Photo by Jeremy Moeller/Getty Images) Getty Images
While headphones are nothing new, the way we consume audible media definitely is. Streaming platforms have spurred the rise of highly personalized listening habits — whether it’s a curated playlist, podcast or audiobook you’re listening to on-the-go. Headphones not only signal your taste in music, but also your personal style. And, like any fashion accessory, you can curate your headphone rotation to fit all kinds of outfits and functions, like if you prefer wired EarPods for work calls, bluetooth earbuds for exercising, or over-ear headphones for traveling and running errands.
Whether you’re upgrading your tech game or on the hunt for a stylish gift for him or her that they’ll actually use, there are so many new fashionable headphones to shop that come with special features like total noise cancellation, high-quality microphones, luxurious leather lining, and plush cushioning. Ramp up the volume with these trendy It-headphones that come in a variety of shapes, sizes, and head-turning styles.
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Apple AirPods Max Wireless Over-Ear Headphones
Timothée Chalamet is seen in New York City wearing Apple AirPods Max headphones on July 26, 2023. (Photo by Gotham/GC Images) GC Images
Apple AirPods Max are undoubtedly fashion’s favorite over-ear headphones. Since their launch in 2020, the luxe-looking headphones have been seen slung around the necks of countless fashion week show-goers and the most style-savvy celebs. On top of their lustrous, sleek aesthetic, these headphones render immersive noise cancellation and spatial audio listening features, along with memory foam ear padding and a 20-hour battery life.
Price upon publish date of this article: $479
Courtesy of Amazon
$479 $549 13% off
Apple AirPods Pro 2nd Gen Headphones
A Paris Fashion Week guest is seen wearing Apple AirPods headphones on June 21, 2023. (Photo by Jeremy Moeller/Getty Images) Getty Images
Apple Airpods Pro are a subtle statement if wire-free listening is your jam. The 2nd Gen iteration comes in several size options for a custom fit and floats in the ears to deliver exceptional sound quality. And they come with a USB-C compatible charging case, so you can conveniently charge your laptop and headphones with the same cord. Take cues from Rosie Huntington-Whiteley or Camila Cabello, who’ve been seen in their AirPods Pro while running errands or on the way to a workout.
Price upon publish date of this article: $189
Courtesy of Amazon
$189 $249 24% off
Apple EarPods Headphones
A London Fashion Week guest wears Apple EarPods headphones in September 2022. (Photo by Jeremy Moeller/Getty Images) Getty Images
Believe it or not, wired EarPods are in. Perhaps it was Lily-Rose Depp who started the trend when she was routinely spotted tethered to her tech in 2022, or it was the work of Instagram account @wireditgirls that fixed the headphone style into It-girl status. Or maybe enough style stars lost a mate in their earbud pair so they reverted to a tried-and-true option. Whatever the case, Apple’s EarPods are a favorite celebrity headphone style, as seen on Emily Ratajkowski, Bella Hadid, Adriana Lima, Justin Timberlake, Hunter Schafer, and countless off-duty models at fashion week.
Price upon publish date of this article: $16.99
Courtesy of Amazon
$16.99 $29 41% off
Koss Porta Pro On-Ear Headphones
The viral Koss Porta Pro headphones have over 35 million views on TikTok, with approval from Gen Z fashion influencers like Emma Chamberlain. They’re surprisingly affordable for their ultra-retro aesthetic and high sound quality, along with an in-line wire microphone and convenient collapsable design.
Price upon publish date of this article: $34.99
Courtesy of Amazon
$34.99 $59.99 42% off
Beats Studio Pro Wireless Headphones
Sarah Jessica Parker sports Beats headphones on a stroll in New York City. (Photo by Jose Perez/Bauer-Griffin/GC Images) GC Images
Beats Studio Pro Wireless headphones have been around for over 15 years, but their newest upgrade offers satin-finish, neutral colorways that are sported by celebs like Sarah Jessica Parker, Bella Hadid, and Selena Gomez. With wireless bluetooth connectivity, two listening modes, a USB-C port, and up to 40 hours of battery life, these headphones are ideal for chic travel gear or for sophisticated listening on the go.
Price upon publish date of this article: $349.95
Courtesy of Amazon
$349
Sony WF-1000XM5 Earbuds
These brand new silver earbuds from Sony practically double as earrings. They shine for their metallic detailing, high-resolution audio, AI noise reduction, built-in Amazon Alexa function, and water-resistant protection. Plus, they’re made with recycled plastic and come delivered in sustainable packaging.
Price upon publish date of this article: $278
Courtesy of Amazon
$278 $298 7% off
Bose QuietComfort Wireless Headphones
NEW YORK, NEW YORK – FEBRUARY 12: A guest wears black headphones from Bose, black sunglasses , a white hoodie sweater, a black long coat, outside Ulla Johnson, during New York Fashion Week, on February 12, 2023 in New York City. (Photo by Edward Berthelot/Getty Images) Getty Images
When Lily-Rose Depp isn’t plugged into wired headphones on the streets of New York City, she’s posting selfies at home of her blocking out the buzz in Bose’s new QuietComfort Wireless Headphones. She can still opt for a cord with the included microphone audio cable, while sinking her ears into cushioned ear cups that feature total noise cancellation and high-quality audio.
Price upon publish date of this article: $349
Courtesy of Amazon
$349
Beats Studio Buds +
The Beats Studio Buds + will give you Y2K flashbacks. You can match your retro dad shoes (à la Steve Jobs) with these transparent tech-core buds that offer in-ear surround sound, bluetooth connectivity, and a variety of silicone tip sizes to fit your ears.
Price upon publish date of this article: $169.95
Courtesy of Amazon
$169.95
Marshall Major IV On-Ear Headphones
Model Dana Smith is seen wearing Marshall headphones outside the Louis Vuitton show during Paris Fashion Week in March 2023. (Photo by Daniel Zuchnik/Getty Images) Getty Images
Marshall’s popular Major IV headphones are wrapped with textured vinyl for a distinct vintage flair, and have been embraced by tastemakers like Zoë Kravitz, who often wears hers with a city-chic street style look. These on-ear headphones feature updating ear cushioning and an ergonomic design for long-wear comfort, with new fold clips for easy storage in your go-to shoulder bag. There’s even a bonus jack, so a friend can tune into your sound with you.
Price upon publish date of this article: $113
Courtesy of Amazon
$113 $149 24% off
Sennheiser Momentum 4 Wireless Headphones
The Sennheiser Momentum 4 Wireless Headphones will add a touch of shine to any outfit with the new black and copper colorway. Music lovers will relish in the ability to customize listening preferences in the paired app, along with optimal audio resolution and adaptive noise cancellation features. You’ll never be caught in dead air with these women’s and men’s headphones, as they hold a charge for up to 60 hours of playback time.
Price upon publish date of this article: $299.95
Courtesy of Amazon
$299.95 $399.95 25% off
Bang & Olufsen Beoplay EX Wireless Earphones
Best for those who love dressing in buttery beige tones, Bang & Olufsen Beoplay EX Wireless Earphones are minimal and chic, while still providing a stellar sound experience. Their clean design, coupled with noise cancellation technology and finely tuned acoustics, make these stylish earbuds a sonic standout.
Price upon publish date of this article: $378.81
Courtesy of Amazon
$378.81 $399 5% off
Master Dynamic MW75 Wireless Headphones
The new colorways of Master Dynamic’s MW75 Wireless Headphones fit right in with your morning commute — their design was inspired by urban architecture. The ear pads and headband are crafted with soft lamb leather, so they’re comfortable whether on your head or resting on your neck, and the ear cups feature aluminum and ornate tempered glass.
Price upon publish date of this article: $599
Courtesy of Master Dynamic
$599
Jabra Elite 8 Active True Wireless Earbuds
Whether you’re heading to pilates, the gym, or scaling the city blocks, Jabra Elite 8 Active Earbuds are a sleek style for a sweat sesh’. They come in four matte colorways to match your workout clothes and are waterproof, drop-resistant, and designed to cling to the ears no matter the intensity of your activity.
Price upon publish date of this article: $199.99
Courtesy of Amazon
$199.99
Bowers & Wilkins Px8 Over-Ear Wireless Headphones
These Nappa leather headphones from Bowers & Wilkens will rival even your most luxe designer handbags in quality and feel. They feature an updated acoustic system for sharp sound clarity, two external microphones for amazing call and audio recording quality, and innovative cushioning that’s designed to mold to your head shape without digging in.
Price upon publish date of this article: $519
Courtesy of Amazon
$519 $699 26% off
Top Stylish Headphone Accessories
Beyond the built-in aesthetics of the coolest headphones, you can customize your tech with fashionable accessories, too. There’s always a room for added flair, and there are so many ways to deck out over-ear stylish headphones, wireless buds, and even wired EarPods. You can stock up on printed AirPods Max covers to diversify their outfit impact, add a necklace or earring chain to earbuds that also prevents them from getting lost, or cop a designer case to match your favorite handbag.
Earring Clip For AirPods Pro
Price upon publish date of this article: $6.99
Courtesy of Amazon
$6.99
Wildflower Airpods Max Case
Price upon publish date of this article: $19.99
Courtesy of Amazon
$19.99 $24.99 20% off
Bottega Veneta Intreccio Airpods Pro Case
Price upon publish date of this article: $181.19
Courtesy of Bottega Veneta
$250
Airpods White Pearl Chain Necklace
Price upon publish date of this article: $13.99
Courtesy of Amazon
$13.99
Geekria Flex Fabric Headphones Ear Covers
Price upon publish date of this article: $10.95
Courtesy of Amazon
$10.95 $11.88 8% off
Why Trust WWD
Since 1910, WWD — often referred to as “the fashion bible” — has been the leading industry voice of authority for senior executives in the global women’s and men’s fashion, retail and beauty communities, while also informing the consumer media that cover the market. Today, WWD’s breaking news and trend coverage continues to be a trustworthy resource for both fashion insiders and consumers alike. Our shopping editors continue to uphold WWD’s editorial standards and values with quality, expert-backed product selections. Learn more about us here.
Meet the Author
Olivia Cigliano is a Commerce Writer & Producer at Footwear News and WWD where she writes shopping content across fashion, beauty, footwear, TikTok style trends, and more. Cigliano received her bachelor’s degree in journalism from Emerson College, and her byline can be found in publications including Elite Daily and CR Fashion Book. She is currently based in New York City. On her commute to WWD’s office, she can be seen plugged into to her favorite playlists and podcasts on her reliable wired Apple EarPods Headphones or heading to a workout class in her Beats Studio Pro Wireless Headphones.
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