The Most Outdated Outfits Blake Lively Has Ever Worn

From her stint as "Gossip Girl" fashionista Serena van der Woodsen to navigating her real life as a high-profile celebrity mom, Blake Lively has undergone a dramatic style transformation. This isn't unusual for a celebrity with more than a few years in the spotlight, but what is unusual is that Lively acts as her own personal stylist.

Lively once explained this surprising and labor-intensive decision during an interview with Glamour, jesting that it's "probably because I have control issues and a big ego." More than that, the actor sees it as another avenue for artistry. "I love design and I love fashion, and it's a way to be creative," Lively told the outlet. "In my job, I get to be creative, but it's over a period of time and so many other people are involved." In contrast, curating her wardrobe gives Lively an independent project that delivers near-immediate satisfaction.

Really, it's no surprise that such an imaginative personality would need more than one creative outlet, but this means that Lively is taking on all the risk of success or failure when an outfit hits the public eye — and, occasionally, those ensembles end up on the wrong side of style. From outfits that seemed on-target only to age poorly to those that were regrettably passé from the start, Lively has showcased more than her fair share of outdated styles.

Look, 2005 wasn't easy on anybody's fashion sense, including young stars just trying to find a friendly audience — case in point, Blake Lively's ensemble at the Nickelodeon Kids' Choice Awards that year. The actor was riding a wave of success following her breakout role as Bridget in "The Sisterhood of the Traveling Pants," and her award-show appearance was a painfully accurate representation of the era's tween trends.

Let's talk it out from head to toe. First, there was the layered top, which consisted of a baby-blue camisole beneath a sheer and sparkly pink crop top. The cami even had a mandala-esque design printed in gold and black ink, evoking every pseudo-bohemian design that cluttered our early-noughties closets. Skipping over the obligatory 2005 stripe of bare midriff, we can take in Lively's ripped and low-slung jeans, which were, of course, accented with a pastel and bedazzled belt slung loosely over the actor's denim-clad hips (rather than pulled through the belt loops).

Beneath the jeans' thickly cuffed hems, Lively finished the ensemble with a pair of sparkly pink pumps that could have come straight from Elle Woods' closet in "Legally Blonde." The total effect was a perfect snapshot of 2000-era fashions, so while it may make us cringe now, it was at least in line with trends at the time.

We give credit where credit is due: Blake Lively quickly stepped up her red-carpet style after that über-casual first showing in 2005, but it still hasn't been smooth sailing for the "A Simple Favor" actor. Even some dresses that passed muster at their debut — like her overly detailed look for the 2011 Elle Style Awards — now seem dated in retrospect. Lively arrived at the event in a tiered Emilio Pucci gown constructed of diaphanous, cobalt-blue layers. This vivid, electric hue was trendy that year, so the look gets points for relevance, but that iconic color choice also planted the dress thoroughly in its era.

The gown's excessive detailing further dated the ensemble, succumbing to a distinct more-is-more mentality that wouldn't even fly with today's dopamine-dressing maximalists. Consider the whole look: the high-low hem, the dance-ready layers, the half-hidden under-bust cutout, the Y2K-worthy bandeau neckline, the gold chain accents, and the apropos-of-nothing magenta peep-toe heels. It's a lot to take in.

From a modern perspective, we'd argue that the dress could have looked elegant with half as many features — and probably would have maintained a more timeless aesthetic in the process. As it stands, though, this dress represented its time period a little too well, resting on the cusp between noughties bling and 2010s quirkiness.

If fans thought the 2012 conclusion to "Gossip Girl" would slow down Blake Lively's fashion experimentation, they had another thing coming, as the actor has continued to take style risks. For instance, her 2015 press tour for "The Age of Adaline" included a stop at an Apple Store in New York City, where the retailer was hosting a series of celeb events called "Meet the Filmmaker." Lively was one of the special guests, and the actor couldn't have styled herself any further from Apple's futuristic aesthetic than with her rustic, lace-trimmed minidress.

Unfortunately, this risk didn't pay off. We don't hate Lively's bohemian approach, but the dress itself came off as clumsy. The frock incorporated a patchwork of different colors and boho prints that made its pattern inherently busy, even before the addition of chunky lace trim in burgundy, white, and faded sea foam. This lace formed a high neckline and a square, capelet-like shape around the shoulders, creating a boxy silhouette. The dress also bunched around the belly when Lively sat down, disrupting the garment's design, though, to be clear, this is no fault of Lively's body and all to do with the dress' material.

Ultimately, this dress was simply too much. Its aesthetic seemed unsure of its destination, wrestling between a Victorian parlor and "Little House on the Prairie." Sadly, none of these vibes were particularly on-trend in 2015, making Lively's lace minidress an outdated look on all fronts.

As the years go by, Blake Lively's interest in vintage-adjacent fashions only seems to grow. Time and time again, the "Green Lantern" star has surprised onlookers with a curiously old-fashioned sensibility — sometimes with great success, and sometimes not so much. Unfortunately, her look at the 2017 Time 100 Gala was one of her missteps.

We'll admit that the quality of work on her Marchesa dress was stunning, but there were too many competing elements. Between the plunging scalloped neckline, the sheer sleeves, the extensive floral embroidery, and the thick fringe of rainbow tassels, even an appreciative eye hardly knew where to look at this intricate piece. Was it giving sexy dancer, brocade grandma couch, or even tasseled silk lampshade? If we can't decide, that's a bad sign.

And this dress was not a one-off stumble. In the years since, we've also seen other floral outfits flop from Lively. On the one hand, it seems like she's not taking notes from her less-than-successful outfits, but on the other, we love that she's still willing to push boundaries with unusual fashion. We'd rather see the "It Ends with Us" actor continue dressing in bold, eccentric pieces that don't always work than get discouraged and play it safe.

Blake Lively knows how to have fun with fashion — there's a reason she acts as her own stylist, after all — and we'll confess that we still kind of like most of the outdated outfits she's worn. But if there's one item on this list that made us hide our faces in our hands, it's the bamboozling Prabal Gurung gown Lively wore to the "Free Guy" premiere in 2021.

The dress' eye-catching metallic pink fabric was enough to turn heads on its own, but it wasn't left to do the heavy lifting in a simple silhouette. Instead, it was twisted into a tortured, skin-baring design that would have looked more at home on Christina Aguilera circa 2000. It's true that Y2K fashion has trended again in the past few years, but execution still makes a difference. Here, the huge cutouts did nothing to help the dress' shape or elegance, and the bulky, off-kilter bust coverage failed to create a good shape or flow.

Worse still, Lively can't hide behind the passage of time as an excuse — 2021 is still recent enough that she should have known better. We love Lively for both her talent and adventurous spirit, but this undeniably outmoded throwback look should have literally been thrown back instead of trotted onto the red carpet.