16 Years of Who What Wear: Every Iconic Fashion Moment From 2006 to Today

Sixteen years ago, Who What Wear was born out of a goal to make fashion and style accessible for all. It certainly has been a wild ride, starting as a little site in 2006 and growing into the brand you currently read (and shop from) today. We launched two brands (Who What Wear x Target and Who What Wear Collection) and are finding new ways every day to connect with our readers on a deeper level. Not only has a lot changed for us, but the sartorial world also isn’t the same it was in 2006. We thought we’d take a trip down memory lane and remind you of all the fashion moments we’ve reported on since WWW’s inception. Be prepared to be filled with nostalgia and have the desire to dig into your old stuff or have a laugh at some of the things you thought were très cool. Trust us—we felt the same way. We’ve rounded up our fashion favorites from 2006 to 2022, from hot-pink Motorola Razrs to sultry cutouts. This is not a comprehensive list of everything from the past 16 years, but it’s a pretty good summary. 

We don’t want to keep you waiting, so you can just go ahead and keep scrolling to step into our little time machine.

No handbag managed to have quite the grip on popular culture in the mid-2000s like Balenciaga’s City Bag did. The slouchy, convertible satchel featured the brand’s signature edgy hardware that served as its only identifiers, without a single logo in sight. Though the brand recently released a modern iteration, the original still continues to be a hot-ticket item on the resale market.

Fun fact: In 2006, Who What Wear’s co-founders Hillary Kerr and Katherine Power published their very first trend report entitled “Little Leather Jackets.” Although the story itself is now buried in the internet’s endless backlog, the trend lives on through the plethora of celebs like Rachel Bilson who ignited the look.

Nothing says 2006 quite like a denim cutoff miniskirt. Rihanna wore them in Hollywood. We wore them through the halls of our middle and high schools. It was truly a trend everyone was in on.

In Laguna Beach and The Hills, Lauren Conrad had us all glued to our TV screens to soak in her every (very stylish) move, with friends and co-stars Audrina Patridge and Whitney Port by her side. Chandelier earrings, tube tops, and plenty of stacked bangles became her style signatures.

Givenchy may have introduced the Nightingale bag in 2006, but the oversize leather carryall managed to remain a fixture on the arms of street style stars and celebs alike in the years following its launch. Notable fans of the satchel bag include Kendall Jenner and Keira Knightly.

The first episode of Gossip Girl aired on The CW this year, and the show promptly assumed its position as the cultural bellwether of the era. Nothing from the show’s wardrobe was more influential than Blair Waldorf’s collection of preppy headbands, we’d argue.

After the duo’s steamy on-screen romance in Mr. and Mrs. Smith, Angelina Jolie and Brad Pitt made things official IRL. The pair subsequently walked many red carpets together, and their understatedly cool style as a couple was simply unmatched.

Why yes, this is a photo of Kate Middleton carrying a Longchamp Le Pliage Bag to her college graduation. This image may have been snapped in 2005, but it’s safe to say the bag was a true cult piece in the mid-2000s. As a testament to its longevity, the classic bag is still popular to this day.

Chloé’s Susanna Boots, a pair of leather ankle boots adorned with a swirl of studs and metal buckles, were originally released in 2008. As anyone with a Pinterest account during this era would know, seemingly every celeb, model, blogger, and fashion person had these boots in their closets, and we have the street style shots to prove it.

Katie Holmes and Tom Cruise were the subjects of endless headlines this year and were crowned Hollywood’s unofficial It couple of the mid-2000s. Who could forget when their daughter Suri graced the cover of Vanity Fair alongside her famous parents?

When we say that this Balmain military-style jacket defined fashion this year, we don’t think that’s an exaggeration. Beloved by Beyoncé, Rihanna, and plenty more A-listers, the designer piece ignited the trend of structured and embroidered outerwear that would reign supreme for seasons to come.

Proenza Schouler’s PS1 messenger bag was the ultimate cool-girl carryall in 2009 that’s both polished and lived-in. The slouchy satchel shape features a top-handle and crossbody option that stars such as Nicky Hilton, Kate Bosworth, and Emma Roberts were fans of.

Alexander McQueen’s iconic skull scarf was released in 2003 but reached a fever pitch in popularity in the early 2010s.

Of all the iconic accessories to emerge from Phoebe Philo’s stint at Celine, none had quite the impact that the Luggage Bag did. Twenty-ten was the year bags went from slouchy to structured, and Celine’s It bag marked this pivotal shift.

We could sit here and debate the trendiness of skinny jeans all day long, but there’s no denying that slim-fit denim reigned supreme during this era, and celebs were especially keen on styling them with patent pumps and flowy blouses.

From the pages of Tumblr to the streets of NYC and Paris, Jeffrey Campbell’s Lita Boots really took hold in the early 2010s. The platform lace-up boots were everyone’s must-have, and to our surprise, celebs even forewent their designer options for this more affordable pick.

It’s impossible to scroll through a street style gallery without spotting a Chanel bag, but the fashion set was particularly obsessed with the structured Boy Bag this year.

Flannel shirts (along with messy topknot hairstyles—hi, Miley!) absolutely dominated 2012. Flannels had a big moment thanks in part to Rails, whose super-soft Hunter shirts were loved by celebs and, quite frankly, still are.

Mansur Gavriel has since created a roster of lust-worthy bags, but this was the year when the brand’s first creation, a sleek leather bucket bag, really took off and put the minimalistic accessory brand on the map.

The term “normcore” started swirling in fashion circles this year to describe a bubbling aesthetic that can only be categorized as anti-fashion. Ordinary basics like plain T-shirts, “dad” sneakers, and non-fitted jeans conveyed a carefully cultivated style.

Chloé has had many of its bags become It bags, but we remember when the Drew Bag was the only accessory street style stars had to have.

When Dylan Lex released her collection of silver jewelry, her statement necklaces were quick to trend. The pieces were spotted on the likes of Beyoncé and Rihanna, and everyone tried to get their hands on a pair or use their DIY skills to create their own.

Don’t you remember saving a variety of ombré hairstyles to your Pinterest board? We sure do. Kylie Jenner’s locks were a part of the edgy aesthetic she had during this era. (Remember Msfts?)

Ah, the world of Tumblr and Alexa Chung’s minimal yet chic style taking the world by storm. Her book was released this year, and we remember rereading each page and bookmarking her looks to copy immediately. Overalls, striped tops, and easy denim were her staples.

Before the rise of athleisure, workout wear was made just for the gym. Comfort became a top priority of the fashion set, and mixing elevated pieces with track pants or sneakers quickly became the norm.

Loafers were always seen as a polished piece in the wardrobe, but when Gucci added a fur lining, the brand brought a trendy element to the shoe style. Dare we say this was the beginning of fur linings being used popularly as an eccentric touch in footwear?

When Alessandro Michele took the reigns of Gucci in 2015, he quickly became known for mixing elements of the brand’s heritage with modern touches. The bag comes in a classic print or with lively embellishments and artwork.

Off-White was founded in 2012, but the industrial belt has become Virgil Abloh’s most iconic design. Inspired by workwear, it added a utilitarian touch to the street style scene.

According to Google’s 2016 report, bomber jackets were the number one trend of the year. The outerwear item was worn by a variety of style icons, from Kanye West and David Beckham to Gigi Hadid and Kendall Jenner. Although the piece has military roots, it became about style as well as utility.

Although they are not still together, Bella Hadid and The Weeknd are still the über-cool celebrity couple on people’s minds. When they took to the Met Gala red carpet together, people were in awe. (We still are.)

Tiny bags have come and gone out of style, but you can thank Jacqeumus for truly putting the style on the map in the past few years. 

Balenciaga’s Triple S sneakers and Fila’s Disruptors truly had a chokehold on fashionable people everywhere. Although controversial and considered “ugly,” their popularity showed otherwise.

Do you remember walking past the Supreme store and seeing a line that stretched for blocks and being shocked? Us too. People were stalking the brand’s site to get their hands on anything that had the simple logo, from lighters to bricks.

Although the high ponytail was a favorite hairstyle among many for its easy styling, we have to admit that it did come with some added headaches.

John Galliano may have debuted the Saddle Bag on the runway for his 2000 collection, but the style made a return in 2018 as if nothing had changed in 18 years. After many design reiterations, the bag is still a staple.

While Ganni may be recognizable by every fashion insider now, that wasn’t always the case. The brand took to Copenhagen runways and blew everyone away, and it’s only gone up from there. 

We’d be lying if we said we didn’t wake up early in the morning to watch the live stream of Prince Harry and Meghan Markle’s wedding. We’ve loved every bit of their royal romance, from their engagement to the births of Archie and Lilibet.

When Daniel Lee took the hold of Bottega Veneta, he skyrocketed the brand into cult status. Although the bags weren’t branded like most designer handbags, that didn’t change the fact that everyone wanted one and could recognize Lee’s design instantly.

Remember when everyone wore fitted suiting? Good times. In the past few years, oversize suiting has become the go-to ensemble for looking forward and cool.

We still remember when everyone was wondering whether Hailey and Justin Bieber were secretly married or not. Their wedding pictures were a dream, and we’re always taking notes from their street style looks together.

We’ve been obsessed with Zendaya since her Disney days, but when Euphoria and Spider-Man: Homecoming came out, we wanted more of her on our screens. Her red carpet style just keeps getting better—as do her projects. (We currently have scheduled a day to watch Dune.)

Telfar Clemens founded his brand in 2005 and became a success when his shopper bag—also known as the “Bushwick Birkin”—gained popularity. Clemens aims to make luxury accessible, keeping the bag at a relatively low price point and scheduling “Bag Security Program” days, where dedicated customers can secure their bags.

Quarantine in 2020 meant staying home. Thus, comfort became the number one priority in fashion. Sweatpants, slippers, and socks were the only clothing items anyone wanted to wear. (If we’re being honest, that is still a lot of what we wear right now.)

Raise your hand if you also tried to chop your own curtain bangs in quarantine, because our hands are up. They may be tricky to style, but when they are done right, they look phenomenal.

Bridgerton may have been released toward the end of 2020, but it was exactly what everyone needed as a little bit of escapism. The romance, costumes, and scandal, what was not to love about it? We’re still dreaming about the duke—sorry not sorry.

It seems like there’s a trend of designers rereleasing new versions of old cult bags for them to be cult bags yet again. The new Gucci Jackie is more modern and sleek, with a leather sheen and fun colors, but if you prefer the vintage version, you can easily find one secondhand.

As restrictions were lifted and people became willing to go out again, the fashion trends became a little less about comfort and more about making a vivid statement. Revenge dresses, cutouts, and loud colors galore.

Olivia Rodrigo has come a long way from the girl who sang “Drivers License.” Since then, she’s released her debut album and singlehandedly become the ultimate pop princess for Generation Z.

We’re still coming off the high we got from the Kravis engagement announcement. Can you blame us? Although the couple confused everyone at first, we’re completely on board.

This was an easy one: The Balenciaga Cagole Bag in all of its Y2K glory dominated everyone’s attention in 2022. Fun fact: The Balenciaga City Bag, which the Cagole is inspired by, was the It bag in 2006, the year Who What Wear first came to be.

After years and years of high-rise everything, low-rise is a thing again in 2022—so much so that it actually became mainstream. As trends this massive and significant often do, the low-rise trend is one that’s likely to stick around for some time.

Miu Miu generated many It items this year, but it’s the delicate satin ballet flats that took the fashion world by storm. Not only that, it’s safe to say that Miu Miu played the biggest hand in the overall ballet flats trend. Despite being nearly $1k, they’re sold out practically everywhere. 

What a year Sydney Sweeney has had. Aside from being one of the best parts of Euphoria and riveting viewers in the wildly popular White Lotus, it was announced earlier this year that she’s joining the Marvel Universe in Madame Web. She’s also become a darling of the fashion world, starring in campaigns for Miu Miu and Tory Burch.

Thanks to head womenswear designer Olympia Gayot (who joined the brand in 2020), J.Crew is cool again. And if you need any more validation of something being cool in 2022, Gayot and her effortless J.Crew styling regularly go viral on TikTok.

Next, The Who What Wear Fall Issue: Your Guide to What Matters in Fashion.

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