Every Iconic Fashion Moment From 2006 to Today

15 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 from a little site in 2006 to the brand you currently read (and shop from) today. We’ve 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 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 we started. 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 was très cool. Trust us, we felt the same way. From hot pink Motorola Razrs to sultry cut-outs, we’ve rounded up our fashion favorites from 2006 to 2021. By no means this is not a comprehensive list of everything in the past 15 years—but it’s a pretty good summary.

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

As a side note: to celebrate our big 15th birthday we’re offering a 15% discount on WWWC as well as a gift with purchase. You can choose from the scarf spotted on the fashion set, Merit’s cult-favorite lip oil, or Versed’s Dew Point moisturizer. We hope you will join us in celebrating our birthday and share the news of our birthday promo.

No single handbag managed to have quite the grip on popular culture in the mid-2000s as Balenciaga’s Moto Bag did. The slouchy convertible satchel featured its 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.

Balenciaga City Classic Metallic Edge Bag ($1250)

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.

Simone Rocha Puff Sleeve Biker Detail Jacket ($1995)

Nothing said 2006 quite like a denim cutoff mini skirt. Rihanna wore them in Hollywood. I wore them through the halls of my middle school. It was truly a trend everyone was in on.

Zara Mid Rise Denim Skirt ($36)

From Laguna Beach to 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 Nightingale Satchel Waxed Leather Small ($885)

Givenchy may have introduced the Nightingale bag in 2006, but the oversized 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 everyone from Kendall Jenner to Keira Knightly.

The first episode of Gossip Girl aired on the CW this year and 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.

Shashi Satin Knot Headband ($55)

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 in fact Kate Middleton carrying a Longchamp Le Pilage 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 in general. As a testament to its longevity, the classic bag is still popular to this day.

Longchamp Large Le Pliage Tote ($145)

Chloe’s Susanna Boots, a pair of leather ankle boots adorned with a swirl of studs and metal buckles, was 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 to show for it.

Chloé Susanna Stud Buckle Bootie ($1380)

When I say that this Balmain military-style jacket defined fashion this year, I don’t think it would be 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.

Etro Braid-Detail Military Jacket ($2670)

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 like Nicky Hilton, Kate Bosworth, and Emma Roberts were fans of.

Proenza Schouler PS1 Satchel Suede Medium ($520)

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

Alexander McQueen Classic Skull Print Silk Scarf ($345)

Of all the iconic accessories to emerge from Phoebe Philo’s stint at Celine, none had quite the impact that the Luggage Bag did. 2010 was the year bags went from slouchy to structured and Celine’s It bag marked this pivotal shift.

Celine Luggage Bag Smooth Leather Medium ($1365)

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

Madewell Roadtripper Skinny Jeans ($75)

From the pages of Tumblr to the streets of NYC and Paris, Jeffrey Campbell’s Lita Boots really took hold in 2012. 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.

Jeffrey Campbell Lita Boots ($160)

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.

Chanel Boy Flap Bag Chevron Nubuck New Medium ($5355)

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 celebs were particularly keen on at the time and, quite frankly, still are.

Rails Hunter Shirt in Sky White Daffodil ($158)

Who could forget the 2013 Met Gala at which “Kimye” first walked the red carpet as a couple, at the time expecting their first North West.

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

Mansur Gavriel Bucket Bag ($695)

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 their bags become their “it bags” but we remember when the Drew bag was the only accessory street-style stars had to have.

Chloé Drew Crossbody Bag ($1360)

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

Dylan Lex Falkor ($1050)

Don’t you remember saving a variety of ombre hairstyles to your Pinterest board? Because we sure do. Jenner’s locks were all a part of the edgy aesthetic she lead 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 re-reading each page and bookmarking her looks to copy immediately. Overalls, striped tops, and easy denim were her expertise.

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.

Adidas Originals Relaxed Track Pants ($70)

Loafers were always seen as a polished piece in the wardrobe, but when Gucci added a fur lining it 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 to footwear?

Gucci Princetown Genuine Shearling Loafer Mule ($995)

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

Gucci Dionysus Suede Shoulder Bag ($2550)

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.

Off-White Industrial Belt ($260)

According to Google’s 2016 report, bomber jackets were the #1 trend of the year. The outerwear item was worn by a variety of style icons from Kanye West and Devid Beckham to Gigi Hadid and Kendall Jenner. Although the piece has military roots, it became about style just as much as utility.

Free People Duvet Bomber Jacket ($148)

Although they may not be together, Bella Hadid and The Weeknd are still the uber-cool celebrity couple 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.

Jacquemus Le Chiquito Bag ($550)

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

Topshop Cherry Trainer Sneaker ($58)

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

Supreme Big Arc Crewneck ($287)

Although the high-ponytail was a favorite hairstyle among style many for its easy styling, we have to admit, 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.

Ganni Wool Mix Knit Cardigan ($285)

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’s Wedding. From their engagement to the birth of Archie and Lilibet, we’ve loved every bit of their royal romance.

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, it didn’t change the fact that everyone wanted one and could recognize Lee’s design instantly.

Bottega Veneta The Pouch Large Gathered Leather Clutch ($2790)

Remember when everyone wore fitted suiting? Good times. In the past few years, oversized suiting became the go-to ensemble to look forward and cool.

H&M Gathered-Sleeve Jacket ($50)

We still remember when everyone was wondering whether Hailey and Justin 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 Spiderman: 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” took popularity. Clemens aims to make luxury accessible, keeping the bag at a relatively low price point and scheduling “bag security” days where dedicated customers can secure their bags.

Telfar Medium Puff Shopper ($260)

Quarantine in 2020 meant staying home so thus comfort became the #1 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.)

Ugg Classic Mini Ii Genuine Shearling Lined Boot ($150)

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, they look phenomenal.

Bridgerton may have been released at the near 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 re-releasing new versions of old cult bags for them to be cult bags yet again. The new Gucci Jackie is more modern and sleek with the leather sheen and fun colors, but if you prefer the vintage version you can easily find one secondhand.

Gucci Jackie 1961 Small Leather Shoulder Bag ($2500)

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, cut-outs, and loud colors galore.

Superdown Kory Choker Dress ($66)

Olivia Rodrigo has come a long way from the girl who sang “Driver’s License”. She’s since then 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.

Next, The Who What Wear Fall Guide Is Here With Every Fashion-Insider Thing to Know

This article originally appeared on Who What Wear

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