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

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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 also the sartorial world isn't the same as 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.

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It Bag: Balenciaga City Bag
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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.

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Overall Trend: Shrunken Leather Jackets
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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.

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It Item: Denim Miniskirts
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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.

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It Girl: Lauren Conrad
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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.

It Bag: Givenchy Nightingale Bag

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Most Watched TV Show: Gossip Girl
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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.

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It Couple: Angelina Jolie & Brad Pitt
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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.

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It Bag: Longchamp Le Pliage Tote
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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.

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It Shoes: Chloé Susanna Boots
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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.

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It Couple: Katie Holmes & Tom Cruise
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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?

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Overall Trend: Military-Inspired Jackets
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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.

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It Bag: Proenza Schouler PS1 Messenger Bag
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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.

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Must-Have Accessory: Alexander McQueen Skull Scarf
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Alexander McQueen's iconic skull scarf was released in 2003 but reached a fever pitch in popularity in the early 2010s.

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It Bag: Celine Luggage Bag
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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.

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Overall Trend: Skinny Jeans
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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.

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It Shoes: Jeffrey Campbell Lita Boots
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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.

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It Bag: Chanel Boy Bag
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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.

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Overall Trend: Flannel Shirts
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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.

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2013 It Bag: Mansur Gavriel Bucket Bag
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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.

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2013 Overall Trend: Normcore
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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.

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It Bag: Chloé Drew Bag
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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.

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Must-Have Accessory: Dylan Lex Necklace
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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.

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Most Loved Hairstyle: Ombré Hair
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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?)

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It Girl: Alexa Chung
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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.

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Overall Trend: Athleisure
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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.

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It Shoes: Gucci Fur-Lined Princetown Loafers
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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?

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It Bag: Gucci Dionysus Bag
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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.

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Must-Have Accessory: Off-White Industrial Belt
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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.

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Overall Trend: Bomber Jackets
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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.

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It Couple: Bella Hadid & The Weeknd
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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.)

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It Bag: Jacquemus Le Chiquito
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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. 

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Overall Trend: Dad Sneakers
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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.

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It Brand: Supreme
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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.

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Most Loved Hairstyle: High Ponytail
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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.

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It Bag: Dior Saddle Bag
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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.

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It Brand: Ganni
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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. 

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It Couple: Meghan Markle & Prince Harry
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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.

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It Bag: Bottega Veneta Pouch
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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.

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Overall Trend: Suiting
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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.