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The Best and Worst Celeb Looks for Winter Will Have You Rethinking Your Coziest and Cutest ‘Fits
The seasons, trends and celebrity style. Those three elements tend to be the basis for creating the best wardrobe and maximizing your closet. Considering that, we figure it would be a great idea to round up winter’s best looks, as we start to find ourselves in snowier and chillier territory than just a few months ago. These celebs, like Hailey Baldwin, Rachel Bilson and more, will be sure to give you some serious fashion inspo as we transition from fall freshness to winter wonderful. But don’t forget: unfortunately, not every celeb has their fashion sense on point. So, we’ll be giving you some of the worst dressed folks, too. After all, we refuse to let your look flop on our watch. Scroll through the gallery to see the best and worst dressed celebs of winter, updated weekly.
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Hailey Baldwin, December 26
Look who’s back on the list! Hailey Baldwin, a.k.a. Mrs. Bieber, is a frequent guest of our Best and Worst Dressed lists — and she almost always slays. This cute and casual look is the epitome of, well, cute and casual. The jeans give the ‘fit a nice relaxed vibe and the 23-year-old’s adorable mohair sweater is perfect for a built-in winter snuggle. Plus, if you’re Los Angeles-based, you might not need a jacket, per se. Like Hails, if you accessorize with some black pieces (sunglasses, shoes, bag), you’re good to go. What an easy (and lovely) outfit to emulate this ~snow szn.~
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Julianne Hough, December 28
We totally get it — comfort is key. But Julianne Hough looked a little too shabby chic when she was spotted in this uber casual outfit while out and about. First off, the 31-year-old’s mock turtleneck cropped top is actually quite cute, but it would probably work better with a pair of loose jeans. Secondly, those palazzo pants are just NOT in this season, Jules. And please, please, whatever you do, don’t tuck them into your socks. If we were hanging out at the DWTS pro’s house for the evening, this would be the cutest chill sesh look. But we don’t suggest leaving in it … except to answer the door for pizza.
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Rachel Bilson, December 30
This outfit from the O.C. starlet was so cute, we had to show it with and without outerwear. As an on-the-go ‘fit, the stunning grey jacket goes excellently with Rachel Bilson‘s choice of dress and footwear. Her adorable square-neck dress gave a flexible vibe, like she could sit down for lunch at a high-end restaurant or go kicking around in the park with her daughter, whichever. Plus, the 38-year-old’s purse was a good neutral choice that still gave a little pop of color to the look — leather does go with everything, folks.
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Noah Cyrus, December 31
We all know Noah Cyrus likes to rage, but this New Year’s Eve ‘fit was just a little too much — and not cute enough. The acid wash jeans were actually a pretty cool choice, and they looked quite cute with the white open-toed pumps and her mini bag. And, to be fair, we get what the 19-year-old is trying to achieve with the style of her top … but the cut just doesn’t work for her. The halter sat way too high and puts her in dangerous nipple slip territory at any moment. While that was probably her intention, it’s definitely not a fun or functional ‘fit.
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Nikita Dragun and Erika Costell, January 1
Double trouble! It was tough for us to pick who did it better, YouTuber Nikita Dragun or fellow vlogger Erika Costell … so we figured we’d give them both credit for a job well done. Nikita, 23, rocked a super hot teal dress — and we just love when she matches her hair to her ‘fit. Erika, 27, opted for the sickest and most sparkly see-through pants, sporting a sexy thong underneath. Plus, that blazer jacket over the shoulders? Power move, y’all. Looks like these two YouTubers have been taking style notes from some of the trendiest A-listers.
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Joey King, January 7
All we can say is “wow.” Actress Joey King really stole the show in this gorgeous mini dress while attending Deadline’s The Act screening and panel in Los Angeles. The piece in question, by Olivia Rose The Label, complimented the starlet’s softness with a sweet pale blue. Plus, the brocade fabric brings such an old-school regal vibe to the ~lewk~. We all know embellished sleeves are in … but there’s a way to do it and still look like you live in the year 2020. Stunning!
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Jenny McCarthy, January 7
We get taking risks … but actress Jenny McCarthy should’ve weighed her options before taking this one. Her choice of dress for the Fox TCA Winter Press Tour All-Star party in Los Angeles was a bit of a misstep. Though it fit her like a glove, the acid wash/tie-dye feel of this bodycon ‘fit was just a little too messy for our liking. Neon colors have been all the rage lately … but this attempt is a bit too try-hard. And thus, try again!
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Duchess Meghan, January 7
Royally radiant! Duchess Meghan (née Markle) stunned in this gorgeous brown monochrome look while visiting Canada House in London with husband Prince Harry. Her choice of a light brown turtleneck with a silken, deeper brown skirt is so pleasing to the eye — plus, her heels match her skirt. Pair the whole look with her deep beige coat and you’ve got yourself a winter outfit that is definitely fit for a queen (or duchess, or princess, whatever floats your boat).
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RuPaul, January 8
Usually, we love the ‘fits the legendary RuPaul serves us, but everyone has bad style days, y’all. This all-black outfit the famous drag queen wore to appear on Jimmy Kimmel Live would’ve given us just the right witchy vibes … if it weren’t for the ill-fitting jacket. We would’ve loved to see something a little more standard — maybe a satin single-breasted blazer instead. It really is a shame because the rest of the look is actually on point. You live, you learn.
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Rachel Brosnahan, January 7
This is how you do neon right. Actress Rachel Brosnahan showed up to Jimmy Kimmel Live in this stunning and sleek neon green dress by Alex Perry … and we fell right in love. The gown hugs her figure perfectly; It’s simple and unassuming, yet vibrant. Sometimes, less is more, and with that, more is just a pop of color away. Excellent look!
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Cody Simpson, January 11
Talk about a menswear look. Singer Cody Simpson really killed the suit game with this stunning Emporio Armani piece he wore to the Fall/Winter runway show during Milan Fashion Week. The cut of the suit — coupled with the daring choice to go shirtless underneath — really flattered his frame and gave the entire outfit a very finished feel. Plus, his usage of jewelry, light colored boots and his custom Prince Neptune bag (made for him for his birthday by Miley Cyrus) tied the entire ~lewk~ together. Very clean!
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Bella Hadid, January 15
This wouldn’t be the first time Bella Hadid has made our list — on either side of the spectrum. And, to be fair to the model, she definitely gave us a few great looks during her time at Paris Fashion Week. This extremely ’90s outfit was, unfortunately, not one of them. The snakeskin leather pants are incredible … but they lose their flare (no pun intended) when paired with such a casual top and jacket. A tailored, collared blouse or even a simple cropped T-shirt would be a much better choice to pair with such incredible trousers.
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Storm Reid, January 14
If this is what Euphoria star Storm Reid looks like while out and about in Los Angeles, we all need to step up our game. This cohesive and loud look is seriously magical — and definitely has a fall/winter feel to it. Also, those mesh panels in front cuts of the bell of the pants are absolutely delicious, giving us just enough of a look at her legs and strappy heels. Plus, since it is L.A. and everything, we actually really love the crop top choice rather than a longer blouse. Work, girl!
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Tyga, January 15
You know when your favorite jacket starts pilling and you’re super bummed out? That’s what rapper Tyga‘s Paris Fashion Week street style reminds us of. Honestly, this look would have been a solid, stylish yet casual street ‘fit if it weren’t for the stylized fraying of the denim used for the set. Look, he even matched his outfit with his shoes. He tried. We get it, we do. But next time, we suggest something a little less … messy.
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Yara Shahidi, January 15
OK, consider us thoroughly shook. Yara Shahidi really owned this look while appearing on Good Morning America — and despite the color being a little more spring than winter, the entire ‘fit really did its job. An entirely matching style moment can sometimes be hard to achieve, but each piece really seamlessly blended and supported each other with this one. Between those gorgeous long shorts, her cropped jacket and those light gray boots, we’re looking at a fully formed fashion queen. This Black-ish babe knows what she’s doing!
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Bella Hadid, January 21
She’s always on this list in one form or another, huh? Bella Hadid was spotted attending the Alexandre Vauthier runway show during Paris Fashion Week — and needless to say, her adorable ’90s-inspired style really struck gold with this ‘fit. Between the bucket hat, the square-toed boots and the turtleneck/leather jacket combo … we’re seriously inspired. This outfit takes us back in time without being too overt in its nostalgia and it’s definitely easily sourced when it comes to crafting your own copycat look. Excellent job, Bellz!
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Jonathan Cheban, January 22
Sometimes streetwear really hits … other times, it’s just sweats in the street. This, unfortunately for Kar-Jenner BFF Jonathan Cheban, is one of those times. The problem we have with this particular look is the lack of coordination — in fact, that’s what a good streetwear look usually does best. Though it might be just sweats and a good sneaker, usually the ‘fit is put together in such a way that it’s hard to ignore the thought process in the styling. This look is just a thrown together mess, not unlike what we might answer the door for Seamless in. Better luck next time, FoodGod.
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Christie Brinkley, January 22
Our hearts grew three sizes the second we saw legendary model Christie Brinkley in this monochrome look while appearing on Good Day NY. At first glance, we almost didn’t notice that those leather-style pants were deep green, either. Trust us, we were swooning. And it seems as though the 65-year-old knows she did good with this style choice. Let this be a lesson for anyone looking for a sweet yet slick ‘fit for a winter night out!
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Larsa Pippen, January 23
The Kar-Jenner adjacents are far from killing the fashion game this week. KUWTK pal Larsa Pippen was spotted out and about in this windbreaker-esque dress paired with patent leather knee-high boots — and while we get the trend here, we find it to be ill-executed. The dress just isn’t cute (there are certainly better sweater and jumper dresses to fit this whole Ariana Grande idea) and the boots don’t do her slim legs any favors. We don’t necessarily hate this style for you, girl, just … do it better.
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Gigi Hadid, January 22
This off-the-runway look from Isabel Marant finally gave Gigi Hadid that dreamy PFW feel we were hoping to see from her. We’re obsessed with the abstract patchwork on the jacket and how the model made sure her heeled boots complimented the coloring in her outerwear. All in all, the look was structured and made sense whilst still maintaining a simple chicness. She definitely didn’t come to play, y’all — and neither did this ‘fit. After all, it WAS fashion week!
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Taylor Swift, January 24
We’ll admit, she’s not always on the money when it comes to her fashion sense, but when this blonde babe gets it, she really gets it. Taylor Swift attended the premiere of her upcoming Netflix documentary, Miss Americana, at Sundance Film Festival — and as you can see, she owned the red carpet in this matching jumpsuit and jacket. There’s so much to love in this look: the fabric, the cut of the trousers, those shoulders. The silhouette is excellent here … and even more so paired with Tay’s confidence (and a good red lip). Excellent ‘fit!
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Blake Lively, January 28
While we recognize that this look is generally in line with Blake Lively‘s typical street and red carpet style, we do wish she’d jump outside the box just a bit. Prairie dresses and longer, Victorian-style skirts and necklines are super in at the moment — and we’d love to see the blonde beauty flirt with a few custom looks by Batsheva or even Christy Dawn. It’s starting to feel like the same ‘fit over and over, and for the former Gossip Girl, we hate to see that be her fashion fate.
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Tracee Ellis Ross, January 27
Making her mama proud! Actress Tracee Ellis Ross definitely gets her sass from mother Diana Ross — but her fashion sense? Who the heck knows, because it’s so legendary that no one can touch it. The Black-ish star rocked this super sexy blazer and tights combo with a pair of killer red boots and a neon purple Chanel bag on her Instagram and we’re honestly obsessed with the entire look. Literally, there’s not one thing amiss about it … except that, in her caption, Tracee revealed she’d only worn it out for five minutes. A travesty!
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Jessica Simpson, January 29
This outfit singer Jessica Simpson wore to Jimmy Kimmel Live has just about zero redeeming qualities, unfortunately. The hem on the pants is entirely too long for the songstress and the shoulder on the matching blouse are giving us football linebacker vibes. We definitely don’t hate a monochrome look but the tailoring does have to be on point. Plus, cuts that suit you will always fare better — try to nail that bit next time, girl.
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Jodie Turner-Smith. January 29
Talk about pregnancy style done right! Actress Jodie Turner-Smith was spotted in this stunning look (which seems to be head-to-toe Gucci, if we’re not mistaken) while out and about in London and we’re absolutely shook. One thing we see too often when it comes to pregnancy fashion: mama’s not willing to step out of their comfort zone. That doesn’t mean you can’t be cozy, but you can try something exciting and make a statement, just like Jodie. Every aspect of this ‘fit is one for the books, down to the embellished sunglasses. Just stunning (and fun)!
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Heidi Klum, February 4
The legendary model gave us all the winter pastels we could possibly need in this adorable street style look while she was spotted out and about in NYC. Her baby blue coat by STAND is the, well, stand-out of the ‘fit, made even more cozy chic with the oversized sweater underneath. Plus, we love her choice of a casual jean and ankle boot to keep this classic and comfy. Good choices, Heidi Klum!
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Bella Hadid, February 4
Haven’t we seen this look before? The supermodel tends to rely on this type of pseudo-’90s styling in her day-to-day but … we can’t lie, we’re over it. It feels as though we keep seeing almost the same exact outfits on the starlet and we know she can do better. That being said, we do like the denim in this two-piece, especially the way it seems to be distressed or bleached. But until our girl Bella starts switching it up, we can’t praise this look in good conscience. Sorry, boo!
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Jessica Simpson, February 4
Talk about a look fit for NYC! The long-beloved singer definitely has her moments when it comes to slipping up on some style situations — but this incredible Barbie-esque outfit is everything and more. In a Saks Potts coat and a full look underneath by Staud, there isn’t one part of this that doesn’t work. She even paired the pieces with a great Alexander McQueen bag and bright pink sunglasses (most likely Gucci). When Jess gets it right, she really gets it right!
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Alicia Keys, February 6
We’re not a huge fan of Alicia Keys‘ street style while out and about in London, not going to lie. When we give it a second look, we realize that there’s one particular piece in the ‘fit that just doesn’t, well, fit. Had the R&B crooner opted out of the plaid shirt underneath and kept the tube top, we could’ve had a winner here. Sometimes less is truly more, y’all!
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Carly Rae Jepson, February 5
This is crazy but we need Carly Rae Jepsen‘s stylist to call us, maybe, because we’re absolutely obsessed with this suiting! The pastel green and pink is always a lovely color palette to work with and it allows her shoes and bag to pop in all the right ways. Plus, this is one outfit where we can prove that confidence is key — look at that strut. Excellent work, girl.
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Justine Skye, February 12
Well, hello, gorgeous. Singer Justine Skye totally turned our heads in this simple, yet stunning Michael Kors look while attending his runway presentation during New York Fashion Week on February 12. The amount of white in the print pairs perfectly with her heels — and her ash-colored blonde hair really seals the deal here. All in all, we stan an incredible coordinated look. Gorgeous!
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Emily Ratajkowski, February 10
Even models make mistakes, y’all. There’s a lot wrong with this look Emily Ratajkowski was spotted in while out and about during NYFW on February 10. We definitely get going for an oversized look, but the proportions on this suit are just a little to shabby for EmRata’s slim bod. Plus, her blouse doesn’t look like a blouse — it reads more like draped fabric. Finally, her square-toed heels, while cute, just serve to highlight all the flaws this ‘fit has. Definitely disappointing.
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Katy Perry, February 12
This incredible Dundas suit Katy Perry wore to Jimmy Kimmel Live is just too chic and adorable. The color looks excellent on her — especially with her lighter locks. It fits well and she also picked a very cute pair of heels to pair with the eye-catching ensemble. Instead of drawing attention to her feet with a pop of color, she opted for a clear vinyl shoe. Super smart and subtle move, Katy. We seriously love this one.
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Yolanda Hadid, February 12
There’s one big issue with Yolanda Hadid‘s NYFW look on February 12 — that print. The jacket she’s wearing is just not cute … but it would be in a different pattern or even a solid brown. Plus, we’re not into her leopard print mini bag. Sometimes clashing patterns and colors work, it’s true, but you need to know when to take that plunge. It doesn’t seem like Gigi Hadid‘s mom does.
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Zoey Deutch, February 12
This stunning structured suit, worn by actress Zoey Deutch during NYFW on February 12, totally blew us away. In fact, we might dream about it again tonight. The light blue looks just gorgeous on the brunette, but possibly our favorite part of the look is the gingham print blouse underneath. Interestingly enough, it’s not overkill as far as patterns or color is concerned — it ties the whole outfit together. Plus, it fits her like, well, a dream. Just beautiful!
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Harry Styles, February 18
Oh, we’re redefining menswear now? Sounds good to us. Former One Direction heartthrob Harry Styles took to the Brits red carpet in a head to toe Gucci runway look that was both effortless and dated in the best of ways. His signature style has taken a vintage turn and we’re a bit obsessed, especially with the subtle coloring in this ‘fit. The lace collar! The pearls! The menswear take on a classic Mary Jane! We think his smirk says it all — he knows he nailed this one. Excellent job, kid.
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Billy Porter, February 14
Though the Matty Bovan show at London Fashion Week took place on Valentine’s Day, we’re not in love with Billy Porter‘s look from the presentation. Either give that exciting jacket and pair of boots their own spotlight with a tamer pair of slacks or let that dress fly free on its own. We usually love how many risks the Pose actor is willing to take with his style choices — which is why we’re confused why he’s almost trying to hide the most exciting part of his ‘fit.
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Kendall Jenner, February 18
We all know Copenhagen brand Saks Potts is so in right now — but it feels like no one is wearing the label quite like the Kar-Jenner crew. Kendall Jenner brought out tons of smiles at the Sony Music afterparty post-Brit Awards in this cutesy two-piece with a ton of flair. Obviously, she has the bod for this type of look, but either way, she really nailed the sweet simplicity of the ‘fit. But she wouldn’t be the first. Niece North West rocked a similar ensemble from the fashion house back in December 2018.
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Bella Hadid, February 18
Ah, a case of ~too casual~. Bella’s outfits can be hit or miss … but at the Sony Music afterparty post-Brit Awards, she swung and clearly missed. While we don’t entirely hate this as a street style ‘fit, it’s entirely too dressed down for any awards show happenings. Because of its hyper-relaxed stylings, it reads as a big disappointment in that we all know the supermodel is no stranger to a serious, high-fashion ensemble. Come on, Bells!
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Kaia Gerber, February 19
While up-and-coming model Kaia Gerber was out and about in Milan, she gave us a taste of what a simple and elegant winter outfit might look like. Needless to say, we love her for it. This Celine jacket and bag really class up a plain jeans, T-shirt and boots ensemble — and definitely bring those cute cold weather vibes. Plus, we really dig the boxy cut of the cropped coat. Très chic!
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Emily Ratajkowski, February 21
There’s so much to love about this model’s stunning Versace mini suit dress worn to their runway presentation at Milan Fashion Week. Between the pop of cleavage and the bright red color, this is definitely one of EmRata’s best looks. Plus, we get a great look at her incredible legs — which come off extra sexy because of the long-sleeved detailing. We’re pretty impressed with the subtle sexuality of this ‘fit. Gotta hand it to you, girl … this one’s a keeper.
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Tyra Banks, February 25
This ‘fit … would not put Tyra Banks on top. The modeling legend rocked sweats and heels to the Build series in NYC — but totally missed the mark when it comes to classing up the style. There are really chic and exciting ways to make a comfy look go high-end (hello, Ariana Grande) but this look just seems more tired than triumphant in that regard. Just adding Louboutins to your sweats and jeans will not always fire up the ‘fit. We can’t believe we’re saying this, but … take notes, Tyra.
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Harry Styles, February 26
This kid just keeps knocking his looks out of the park lately. In this custom Gucci suit worn during his performance on the Today show, the former One Direction babe gave us all a serious lesson in color blocking. All of the hues work perfectly together, complimenting each other subtly. Topping the outfit off with the polka-dotted tie and white boots gave just the right pops of “color” in the best places. Oh, and that lilac nail polish. *Dreamy sigh*
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Alexa Chung, February 27
We definitely expect better from fashion It Girl Alexa Chung, who wore this mess of a look to sit front row at the Chloé runway presentation during Paris Fashion Week. While we actually like each piece of this puzzle separately, there’s something that really demotes the ‘fit when you put it all together. It might be the choice of combat boots, whereas a set of classic pumps would elevate and class up the leather and fit in well with the lace. Well, you win some, you lose some.
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Hailey Bieber, February 27
This stunning white outfit Mrs. Bieber wore while out and about during Paris Fashion Week is an absolute show-stealer. The pants are just baggy enough to work well with the slouch of her boots — and the matching shades of off-white in the jacket and shoes is totally *chef’s kiss.* And there’s something about the pure white of her turtleneck blouse popping out amongst the cream hue. Talk about a winter wonderland!
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Janelle Monae, March 3
We all know Janelle Monae is a risk-taker when it comes to fashion … so it’s lovely to see her put her own spin on this adorable Chanel suit look while attending their runway presentation during Paris Fashion Week. Between her long braids and the decision to go blouse-less underneath the jacket, we’re super into the crazy edge the singer gave to this otherwise conventionally Chanel ‘fit. It’s definitely not as wild as some of her past outfit choices … but it’s clear she can handle both ends of the style spectrum.
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Ashley Benson, March 2
It’s usually all frills when it comes to Giambattista Valli, we get that. But this look from actress Ashley Benson really misuses the subtle sweetness that comes from the flared fabric. If we could liken this top to anything, it would have to be a bride’s garter belt — because it seems like the Pretty Little Liars alum slipped one around herself and decided it was a good fit. Without that particular accoutrement, we might actually dig this outfit, especially with the tailored slacks. After all, every fashion fail is a learning lesson, people.
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Hilary Duff, March 4
We love a casual queen! Singer Hilary Duff looked too chic in this cute blouse and jeans combo while out and about in Los Angeles. Needless to say, jeans and a solid pair of knee-high boots are always a pretty safe bet when it comes to looking cute and relaxed — but the blonde beauty really amped up the trendiness when she added the long-sleeved patterned shirt. We hope to see more fun, informal looks from the Lizzie McGuire starlet as we start approaching spring!
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Camila Cabello, March 5
Considering Camila Cabello‘s worldwide recognition, you’d think she would have a little bit more style prowess. The brunette beauty walked the carpet at the Global Awards in London — and her look wasn’t exactly a global success. While we would love to see her rock a bustier and a tailored shirt (a classically great and sexy combo), the rose patches really cheapened the ‘fit, as did the black lace skirt peeking out from below. Had she shed those elements of the outfit, we’d be inclined to give it an A+.
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Celine Dion, March 5
Let the style maven do her thing, y’all. Singer Celine Dion was spotted out and about in NYC — and she was serving looks, as usual. This adorable dress and cape combo totally screams Troop Beverly Hills, especially with the knee-high boots and matching hat. Plus, we even love how the Canadian legend styled her hair to give the ‘fit a little extra flair. Not only is this entire outfit a total win, but now we want the songstress to be our Girl Scouts leader.
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Sofia Vergara, March 11
This Modern Family star knows a good winter hue when she sees one, clearly. En route to America’s Got Talent, Sofia Vergara rocked the cutest complementary grey outfit, complete with the perfect accessory: a Chanel bag. Between the jeans, jacket and sky-high heels, it’s clear the Colombia native was going for an icy look with this color-blocking. Simple, yet effective!
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Chloë Sevigny, March 9
Pregnancy style isn’t the easiest to master … and actress Chloë Sevigny has some work ahead of her. Attending the New Group’s 25th Annual Gala in NYC, she was spotted in a ruched floral dress by Preen by Thornton Bregazzi and paired the ‘fit with stark white high socks and loafers. Unfortunately, the look doesn’t really highlight her growing baby bump like we’d like it to — and the choice of sock comes off a little too frat boy for the delicacy of the dress’ print. You’ll get there, girl!
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Emily Ratajkowski, March 11
This Givenchy look from the “Blurred Lines” babe is definitely one of her finer fashion moments. We really love the way she is able to mix casual and business with this cream blazer and white turtleneck paired with a slouchy sweatpant and sneakers. Plus, her puppy, Colombo, isn’t a bad accessory to take with you on a stroll in NYC. Subtle and sexy!
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Rita Ora, March 11
We all know Rita Ora is a style risk-taker … but risks don’t always have the best results. After all, that’s why they’re risks. This white Symonds Pearmain jumpsuit would actually be a pretty cute and casual ‘fit for the singer … but the accent fabric around the neck definitely gives us napkin-in-your-collar vibes. You know, like when you go out to dinner for a messy meal. We just can’t get over it — anyone have scissors?
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Katy Perry, March 11
During a free show in Bright, Australia, the pregnant songstress continued her reign as pregnancy style queen with this adorable neon yellow Givenchy mini dress. The fluff of the sleeves and skirt work perfectly for her growing baby bump and give a little bit of magical flair to the outfit. Plus, those cute blue sneakers add another punch of color. Is it just us or is Katy really killing the pregnancy game? Cute look, love!
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