What’s In Their Wardrobe? // Celebrity Couples Now & Then

With inspiration just a scroll away on Instagram, it’s quite simple to tell which celebrities and influencers have an eclectic fashion taste. And while it may seem like an art form that you’ve got down to a science, what are the odds that your significant other’s style equals your own? This week, we’ve compiled the varied styles of celebrities (currently together or that used to be together) who both excel at street style.

This selection of celebrity couples focuses on the style of then and now, showing the evolution of how much fashion has transformed in just a short time frame. Though the fashion choices of all these tastemakers could still be worn now and not look a stitch out of place, the difference in silhouette, color, and fit is stark in comparison. So who are the celebrity couples today and ten years ago that complement each other’s style so well?

Justin Bieber and Hailey Baldwin

After reconnecting just over a month ago, Justin Bieber and Haley Baldwin have decided to get married. And whether or not all their other similarities and life goals add up or not, their style sure does. In the past couple of years, their style has gone from good to how did you even get your hands on those brands? Oversized jackets, track pants, and plenty of loose fitting sweats, the couple is making the essentials look anything but basic. And what’s more is that their current style rotation seems to complement each other so well, especially when they’re out and about together.

Justin Bieber in the Fear of God New Era cap.
Justin Bieber in the Fear of God New Era cap.
Just kids.
Just kids.
Forget about tailored essentials, loose fitting sweats are in.
Forget about tailored essentials, loose fitting sweats are in.
JB wearing Yeezy Desert Rat 500s. HB wears the adidas Continentals.
JB wearing Yeezy Desert Rat 500s. HB wears the adidas Continentals.
Hailey Baldwin making a case for why the Louis Vuitton Archlight was in our top 20 for Best Releases of 2018 so far.
Hailey Baldwin making a case for why the Louis Vuitton Archlight was in our top 25 for Best Releases of 2018 so far.

His Style

Right after his Purpose album released back in 2015, there was something different about Justin Bieber, particularly his style. And there would be a major shift in his wardrobe when Fear of God announced they would be making all of Bieber’s tour merch apparel. Suddenly, destroyed jeans, cut-off flannels, elongated tees and a rotation between Vans and Ultra Boosts would be the look of LA. We’d eventually see street style savants like Scott Disick, Russell Westbrook, and Kanye adopt the look.

In more recent months, however, Bieber’s look has slightly evolved while maintaining his LA influence, having been seen wearing AMIRI jeans, vibrant Supreme hoodies, and an array of Yeezys – especially the Desert Rat 500.

Justin Bieber wearing Fear of God satin jacket, AMIRI jeans, and Vans Authentics.
Justin Bieber wearing Fear of God satin jacket, AMIRI jeans and Vans Authentics.
Justin Bieber wear OFF-WHITE tee, AMIRI jeans, and vintage Starter jacket with SF Air Force 1s.
Justin Bieber wears OFF-WHITE tee, AMIRI jeans, and vintage Starter jacket with SF Air Force 1s.
All black with a Fear of God Hat and checkered Vans is a no brainer.
All black with a Fear of God Hat and checkered Vans is a no-brainer.
Justin Bieber wears Fear of God Mesh tee, hat, and AMIRI jeans with FOG x Vans 47.
Justin Bieber wears Fear of God Mesh tee, hat, and AMIRI jeans with FOG x Vans 47.
Oakland A's inspired. JB wears Fear of God cap, jeans, and Flaneur hoodie.
Oakland A’s inspired. JB wears Fear of God cap, jeans, and Flaneur hoodie.
Nothing says it's summer like Fear of God mesh shorts and Vans Classic Slip-Ons.
Nothing says it’s summer like Fear of God mesh shorts and Vans Classic Slip-Ons.

Her Style

Hailey Baldwin’s style as of late has officially adopted the boyfriend look. And that’s a good thing because she has one who she’s also engaged to. This look has entailed anything oversized, especially jackets, sweatshirts, and even oversized flannels.

HB has appeared in numerous adidas ads, so it would make sense why her go-to footwear choices have been the Yeezy 700s and adidas Continentals and Stan Smith. The Yeezys allow for a simple option that pairs with loose essentials, like sweats and tees, while the Continental and Stan Smiths go with anything from dresses to cropped jeans and everything in between, thanks to their low-profile designs and neutral colorways.

Hailey Baldwin pairs an oversized flannel with the Balenciaga Triple-S.
Hailey Baldwin pairs an oversized flannel with the Balenciaga Triple-S.
Simplicity that can be met with a timeless icon.
Simplicity that can be met with a timeless icon.
Streetwear essentials that are Clima Cool.
Streetwear essentials that are Clima Cool.
HB wearing the Louis Vuitton Archlight.
HB wearing the Louis Vuitton Archlight.

Ben Simmons and Kendall Jenner

Officially dating? Not officially dating? No comment, but what is official is the fact that Kendall Jenner and Ben Simmons have really good style.

Straight from the 90s.
Straight from the 90s.

His Style

Ben Simmons’ style is the definition of simplicity, usually incorporating some iteration of the upscale athleisure look into his wardrobe. Simmons elevates the sweats and tee combo by upgrading his look with tailored Gucci joggers and fitted tees that are enhanced with OFF-WHITE Air Force 1s. He’s also got the minimal layering look down to a tee by his usual pairings of dark slim jeans with premium flannels and Converse CT 70s.

Ben Simmons wearing Gucci joggers and OFF-WHITE AF1s.
Ben Simmons wearing Gucci joggers and OFF-WHITE AF1s.
Basics that can be elevated with a timeless sneaker pairing.
Basics that can be elevated with a timeless sneaker pairing.
Black and Bred.
Black and Bred.

Her Style

Not only is she one of the most well-known models in the world right now, Kendall Jenner is also making a name for her sense of street style. She’s been on a bit of a 90’s kick as of late, wearing yoga pants with graphic tees. Beyond that, she’s also embracing the trend of cycling shorts with 90’s inspired runners. Her casual style also embraces the LA look from several decades ago that’s now come full-circle, consisting of loose-fitting jeans, crop tops, oversized crewnecks. And having close ties with Yeezy, you know her footwear game consists of A LOT of adidas. Aside from the Three Stripes, there’s plenty of other 90’s inspiration in her footwear rotation, like Vans Old Skools and chunky Balenciaga runners.

Pirate perfection. Kendall Jenner wears the "Pirate Black" Yeezy 350's with cropped jeans.
Pirate perfection. Kendall Jenner wears the “Pirate Black” Yeezy 350s with cropped jeans.
Give your look a boost with some 90s inspiration.
Give your look a boost with some ’90s inspiration.
Kendall Jenner wears Balenciaga coat with Yeezy 700's.
Kendall Jenner wears Balenciaga coat with Yeezy 700’s.

Kanye West and Amber Rose

Back to the days of Pastelle, Bape, and even a Nike deal, Kanye West was dating Amber Rose when their sneaker rotations were unparalleled. Before splitting almost a decade ago, the duo could constantly be seen out in public with the most heat for that particular era. Kanye was pioneering the fashion world beyond everyday sneaker brands and exploring the world of luxury that has now become a mainstay.

Another reason to buy the White Cement Jordan 4s.
Another reason to buy the White Cement Jordan 4s.
Air Yeezy.
Air Yeezy.
The varsity look was as much alive then as it is now.
The varsity look was as much alive then as it is now.
Cementing a legacy in style.
Cementing a legacy in style.

His Style

Revisiting a time where every night was Louis Vuitton Don night, Kanye had broken into the luxury fashion scene with a Louis Vuitton deal. Not only could he be spotted wearing some of the most iconic pieces to have ever released from the brand, he also had several of his own shoes with the LV label, known as the Don and the Jasper, which have released in colorways that have appeared on the resale market, reaching north of five figures.

Near the same time as the Louis Vuttion partnership, his influence landed him his own deal with the Swoosh, where his signature sneakers would also become some of the most coveted to ever hit the footwear market. Soon after this deal came into place, he would form another partnership with minimalist fashion label A.P.C., where he would again find himself designing some of the most iconic pieces to hit the streetwear scene. This would only become the beginning of “The Kanye Effect” that would eventually follow suit.

The Louis Vuitton Don.
The Louis Vuitton Don.
When the look of luxury was a fur coat, leather pants, and Jordan 3's.
When the look of luxury was a fur coat, leather pants, and Jordan 3s.
Kanye recognized the versatility and how timeless New Balance 997's are.
Kanye recognized the versatility and how timeless New Balance 997.5s are.
Defining a new meaning for the term "grails."
Defining a new meaning for the term “grails.”
The clothing brand that started it all.
The clothing brand that started it all.
Bananas for BAPE.
Bananas for BAPE.

Her Style

Much like Kanye, Amber Rose’s style at the time was also very minimal, making it easy for her footwear rotation, usually consisting of Jordans to pop. Whether that be black yoga pants and a leather jacket, it’s pairings like these that set up the perfect pairing to incorporate “Black Cement” Jordan 3s into the mix. And at the time, she had also been seen matching Kanye’s footwear choice on several occasions. Even if it wasn’t the same shoe, it begs the question of if Ye was curating Amber Rose’s style like he is with Kim.

Amber Rose wears all-over paisley print with the Jordan 8's.
Amber Rose wears all-over paisley print with the Fusion Jordan 8s.
When your Jordans have the right accent of black and red to upgrade your kit.
When your Jordans have the right accent of black and red to upgrade your kit.