Every Fashion Person Wears These Iconic $55 Sneakers, so I Bought Them Too

If you had to name one of the most iconic sneaker silhouettes out there, Converse Chuck Taylor All Stars would probably come to mind. The style (which was initially designed as a performance sneaker) has remained in the spotlight since the early 20th century. As we covered recently, the shoes continue to be a staple for many—including the fashion crowd—to complete their chic looks. Honestly, I feel like I see a smattering of outfits featuring Converse every single day as I scroll through IG.

While I recently invested in a pair from the JW Anderson collaboration, I felt inspired to go for a classic pair (those $55 black high-tops) because they honestly can go with pretty much everything and bring that cool, laid-back twist to an ensemble.

Do you live in Converse or want to follow my suit and stock your wardrobe with a fresh pair? Keep scrolling to uncover some of my favorite outfits featuring the iconic sneakers. If you’re interested, I also shopped out the looks in question, including a range of Converse sneakers that start at $55.


(Image credit: @_marisamartins_)

The black-and-white sneakers team flawlessly with the simple yet chic black and white-shirt–and-skirt combo.


(Image credit: @oliviafaeh)

An oversize blazer belted over a tee and skirt is modern and polished with those classic Converse high-tops.


(Image credit: @carodaur)

Can't beat an all-white look for a fresh summer vibe.


(Image credit: @anoukyve)

This ensemble is quite effortless with the relaxed white jeans and breezy blouse.


(Image credit: @kristengracelam)

This ensemble is where it's at with the straight-leg jeans, tee, and Converse. If it's chilly, toss on a leather jacket. If not, go without for an easy summer look.


(Image credit: @hannahfgale)

A pair of Converse high-tops feel slightly unexpected (and so right) with a floral maxi dress.


(Image credit: @fakerstrom)

Keep it sophisticated yet chill with a slouchy blazer, tee, white jeans, and trusty Converse.

Next, check out more cool sneakers to shop now.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.