By Megan Riedlinger
8:13am PST, Dec 27, 2021
_
We love checking out what the stars wear when they're off duty! From adorable athleisure to disastrous denim moments, Wonderwall.com is rounding up the best and worst of 2021 celebrity street style… Socks with sandals? Hailey Bieber pulled off this controversial trend flawlessly in Los Angeles on Oct. 5. The star rocked her black athleisure wear with a bomber jacket, white socks and black sandals for an impossibly cool streetwear look.
Keep reading for more of the best and worst street style fashion moments of 2021…
RELATED: Best movies and TV shows about the fashion industry
_
We loved this purple plaid Vivienne Westwood moment from Irina Shayk on April 28. The model stepped out in matching coordinates that she paired with a low-cut black tee and knee-high boots to complete her look.
RELATED: Best celeb floral fashion moments
_
Obsessed! While Kim Kardashian West was in New York City on Oct. 7 to host "Saturday Night Live," she stepped out in this iconic hot pink Balenciaga number. The reality star's neon crushed velvet blazer paired perfectly with matching satin pants and boots, and she took things to the next level with matching gloves.
RELATED: Zendaya's wildest and best looks
_
Vanessa Hudgens showed off some questionable street style — that top hat! — while stepping out in West Hollywood on Nov. 30. The star rocked the odd headwear with a cropped white sweatshirt, green leggings and the controversial combo of socks and sandals.
_
A stylish Canadian tuxedo? Emily Ratajkowski stunned in an all-denim look in New York City on Nov. 8, rocking a long-sleeved button-down with flared jeans in a matching deep blue shade. When it came time to accessorize, she wisely added a belt and matching boots.
_
Gabrielle Union stepped out in New York City on Sept. 15 in this very unfortunate getup — a fuzzy blue cropped hoodie and a white miniskirt covered in sequins and lace. Adding insult to injury? She finished off the fashion faux pas with white pointy-toe pumps.
_
Cardi B certainly made a statement while stepping out during Paris Fashion Week on Oct. 3. The rapper donned this wild Richard Quinn design — all in a bold Kelly green — that included a ruffled bonnet, a long-sleeved and gloved top and high-waisted pleated pantashoes all in the same shade. And though we appreciated the fashion risk, it still ended up among the worst (and wildest!) street style moments of the year.
_
The chic split top that Kendall Jenner wore in New York City on Oct. 15 marked one of our favorite streetwear fashion moments this year. The sleeveless floral-print piece paired perfectly with her high-waisted and belted black trousers. And we love the way she finished off her cool-girl look with chunky black shoes.
_
That's a whole lot of blue, Gigi Hadid! The beauty stepped out during New York Fashion Week on Sept. 9 in this crazy sleeveless buttoned-up jumpsuit in this very bold color. Making matters worse? She added black sneakers with white shoelaces to finish off the funky look.
_
Not all Chloe is created equal! Bella Hadid stepped out in London on Aug. 19 in this very funky Chloe top, showing off a little skin as she paired it with low-waisted baggy black trousers. She completed her messy look with sneakers and drop earrings.
_
Leave it to a supermodel to stun us with her street style! Alessandra Ambrosio rocked this cool lime green minidress — complete with a collar and ruching at the waist — and paired it with killer tan sandals on the streets of New York City on Sept. 8.
_
Social media star Addison Rae stepped out in Venice, California, on June 19 in this underwhelming ensemble. The TikTok star rocked a black cropped tank top with a net detail along the bottom paired with some baggy cropped trousers and purple sneakers — a look we hope doesn't become a trend anytime soon!
_
Kaia Gerber rocked this darling floral minidress while out in Los Angeles on Sept. 22. The beauty added black boots to the mix, marking this look as the perfect foray into fall fashion.
_
Camila Cabello stepped out in Coral Gables, Florida, on April 29 in this… head-scratching look. It started with a crocheted halter top and gave way to what might be wide-legged trousers or just a disastrous blue skirt. Then she finished things off with white sneakers and a brightly colored crossover bag, leading to one big street style miss.
_
That's amore! Kim Kardashian was dressed for summer as she headed to dinner in Rome on June 29 wearing a silk Galliano minidress covered in cherries and butterflies. While her gladiator-inspired sandals were a nice nod to the city's history, we're not so sure about that cannabis leaf trucker hat.
_
This getup from Kendall Jenner underwhelmed. The stunning supermodel stepped out in New York City on March 21 in this puzzling business-casual look — a white collared shirt underneath a striped sweater vest paired with baggy green trousers and chunky loafers — and we have just one question: Why?!
_
Plaid gone wrong? Here's an example from the usually stylish Hailey Bieber, who stepped out in Beverly Hills on July 6 in this funky fit. The model donned an unflattering cap-sleeved crop top and high-waisted plaid trousers with sneakers while running errands, scoring a fashion miss.
_
Heidi Klum nailed street style in 2021! The model and "America's Got Talent" judge stepped out in Los Angeles on March 29 wearing this sweet floral Zimmermann jumpsuit, accessorizing with the perfect pink strappy sandals and hot pink Hermes bag, delivering one of our favorite looks this year.
_
Another day, another killer jumpsuit! Heidi Klum wore this white long-sleeved jumpsuit with white boots and matching white-rimmed shades out in Los Angeles on April 12.
_
What's happening here? Izabel Goulart stepped out during the Cannes Film Festival on July 8 wearing this puzzling ensemble — low-slung baggy jeans, a matching tiny bralette and jacket combo, bizarre sandals, a chunky gold necklace and pale sunnies.
_
Lady Gaga's sleek white pantsuit by Max Mara was one of the sharpest street style moments so far in 2021! The superstar styled the coordinates, which she wore out in Rome on March 4, with a black top and sky-high platform boots plus a matching white bag by Valentino.
_
Camila Morrone donned a disappointing sweater dress on April 17 while out in Los Angeles. The model-actress rocked the frock, which was unbuttoned at the top and bottom, with white sneakers.
_
Showing how to transition from spring to summer style flawlessly? Alessandra Ambrosio, who stepped out in Los Angeles on May 18 in a white cropped tank top with an unbuttoned white blouse paired with wide-legged, high-waisted jeans, an Hermes belt and white sandals.
_
Zoey Deutch showed off subpar street style in Los Angeles on Feb. 9, stepping out in this intense Canadian tuxedo with chunky black boots.
_
Jessica Alba looked laid back yet super stylish while running errands in Los Angeles on March 30. The actress-turned-business mogul wore a black-and-white striped tee with wide-legged trousers and simple black sandals — a sharp yet casual ensemble.
_
Is it a skirt? Super baggy pants? Katie Holmes stepped out in New York City on June 14 in these jeans that were so wide they were easily mistaken for a floor-length denim skirt. The actress added a simple white tank, brown crossbody bag and white sneakers to finish off her underwhelming ensemble.
_
On June 16, Irina Shayk stepped out in New York City in this unfortunate look — an ill-fitting black corset and low-rise jeans. She finished off the flagrant miss with a pair of chunky boots.
_
Alessandra Ambrosio stepped out in Santa Monica, California, on April 2 in this cute chevron-striped sweater and cuffed jeans. Our favorite part of this look? The way she perfectly matched her sneakers to her sweater.
_
Emily Ratajkowski stepped out in New York City on June 3 in a mismatched and underwhelming getup — a pink and green patterned jacket atop a graphic tee, leggings, sneakers and a green dad hat.
_
Athleisure was a big part of 2021 street style, and Eiza Gonzalez showed us how to do it! The actress left a Los Angeles gym on May 12 in this cute pink workout set that she sported with complementary multicolored sneakers.
Another weird business-casual getup from Kendall Jenner! This time the model stepped out in Los Angeles on May 26 in a buttoned-up vest with baggy black trousers and chunky sandals.
Heidi Klum showed off another awesome floral outfit on April 10 as she arrived for a taping of "America's Got Talent" in Los Angeles. She smartly paired an oversized matching yellow bag and simple sandals with her long-sleeved floral minidress.
Ashley Greene scored a miss in this sloppy (though cozy!) long cardigan. The star wore it over a brown sweater, jeans and boots while out in Los Angeles on May 10.
This pretty white blouse paired with cute cropped fringed-hem denim was a fabulous combo for Sofia Vergara! The star rocked this springy look in Los Angeles on April 11, adding brown peep-toe sandals and a tan bag to finish the ensemble.
On May 6, Miley Cyrus stepped out in New York City in this very bold dress. The one-shouldered floral-print knee-length vintage frock by John Galliano was busy enough on its own, but she also added an equally busy purse to the mix, rounding things out with strappy black sandals.
Leopard and studs! Nicky Hilton Rothschild showed that leopard print can work in the summer when she stepped out in New York City on June 7 wearing this sweet short-sleeved animal-print Ulla Johnson frock. We loved the way she contrasted the delicate print with those embellished pointy-toe flats by Valentino.
Singer Camila Cabello had quite a puzzling street style moment in Beverly Hills on May 12 as she stepped out in beige overalls atop a green striped polo shirt all paired with white platform sneakers.
Pretty in pink! Emma Bunton stepped out in London on June 8 in this bright pink pantsuit with a white blouse underneath and added green platform heels to complete her killer street style moment.
A beanie and cropped separates? Alessandra Ambrosio sported a questionable look while out and about in Los Angeles on March 18 — a crop top and cropped pants combo accessorized with a winter hat and sneakers.
Candice Swanepoel is a model, so it's no surprise she showed off some killer street style in 2021. The beauty donned a ruffled white crop top with high-waisted jeans and white sneakers while out in New York City on June 10.
Hailey Bieber sported a seriously dramatic black floor-length coat while out in Los Angeles on March 9. The model paired the over-the-top piece with a tied-up white T-shirt, baggy cuffed jeans and loafers.
Jessica Alba proved how chic orange and green can look together while out in Los Angeles on April 9. She rocked green cuffed pants and a muted orange blazer — a surprisingly cool color palette — and added a gray tee and brown boots to finish off the funky fit.
Eiza Gonzalez proved that mixing yellows is a fashion disaster. The actress donned a bright gold sweatshirt with mustard leggings as she left a Los Angeles gym on May 5 then added some equally confusing shoes — gray and yellow sneakers with pink laces — to finish off her miss.
Hailey Bieber left a West Hollywood gym on June 10 in this very simple and chic athleisure look — a long-sleeved cropped tee and bike shorts ensemble that she completed with chunky black sandals, an updo and dark shades.
It's way too soon for Halloween, Addison Rae! On Feb. 10, the TikTok star stepped out in Los Angeles en route to the gym in sweatpants emblazoned with bone details, a black tank, a black hat and white sneakers.
On April 11, Heidi Klum continued her stellar street style streak while strolling to a taping of "America's Got Talent." The model donned a cheery lime green blazer over a white top and added light denim jeans and white ankle boots to complete her spring-ready look.
Conflicting stripes score an instant miss! Nicky Hilton Rothschild sported a striped sweater with jeans and a tan coat while out in New York City on April 7, but things went south when she added funky striped sneakers.
Irina Shayk paid homage to queen Britney Spears in New York City on June 3! The model rocked a tee with the singer's image emblazoned on it along with cropped light denim and black boots.
Socks over leggings with Uggs? Even though model Kaia Gerber seemingly pulled off this disastrous combo in Los Angeles on March 9, we're hoping it doesn't catch on.
Sofia Vergara arrived for an "America's Got Talent" taping in Los Angeles on March 30 in this darling leopard-print dress. From the short sleeves to the button detail to the way she paired it with those peep-toe heels and black bag, we loved everything about this getup.
Amelia Gray Hamlin rocked mismatched tie-dye sweats while out in West Hollywood on June 9. While sweatsuits have certainly become a fashion staple post-2020, it doesn't mean this messy look — with a trucker hat to top things off! — gets a pass.
Back on April 26, Kendall Jenner hit the streets of New York City in leather trousers. She styled the super-cool staple with a white crop top and an oversized jacket, adding a tan bag and black boots to finish off her off-duty-model look.
Who doesn't love a wild Rihanna street style moment? Unfortunately, this look she wore to dinner in Santa Monica on May 5 was just a little too over-the-top between the blue feathered jacket and belted lime green tie-dye pants.
Want to wear a sweater in the hotter months? Alessandra Ambrosio showed how, rocking her cute varsity-style knit with short denim cut-offs and adding slouchy socks and loafers to keep the look preppy.
Kim Kardashian's Roman holiday over the summer featured a lot of great fashion — but this look wasn't part of that. She wore a black leather trench coat in Italy on June 30, pairing the dramatic piece with a black tank top, camo pants and sneakers.
A pale green pantsuit made for an unexpectedly chic street style moment from Heidi Klum as she stepped out in Los Angeles on April 23. The model paired the coordinates with a white sweater underneath and — the best part of all — white and green platform sneakers.
