Hailey Baldwin is the name on everyone’s lips recently, and it’s not just due to the fact that she’s about to be wed in the holiest of matrimonial ceremonies to Canada’s arguably unfortunate claim to fame, Justin Bieber. Hailey Baldwin’s career is basically turning into the 100 emoji: 100% amazing.
According to Billboard, Hailey Baldwin rose to fame with a few good contracts for companies like French Connection and Guess and has walked for a number of popular designers, as well worked as a Hollywood actress. Is there anything this woman can’t do? We don’t think so.
Now her name's been on everyone’s lips with her engagement to one of the most well-known celebrities in the world. We’re so incredibly glad, as it means there are going to be even more photos of Hailey Baldwin’s incredible style.
From her signature look of oversized sweaters and baggy pants to fashion-forward duster jackets and sleek crop tops, there’s nothing Baldwin can’t pull off. Her confidence makes it possible to wear anything, but then again, that doesn’t mean she should. Sometimes her outfits are more misses than hits, even though we respect her bold experimentation with fashion. Here are 15 of her most inspiring styles and 5 that she should put away forever.
20 Her Cute And Casual Courtside Look Gets Us Excited, Too
This style is one that we absolutely love. Not only has Hailey embraced the current trends in this outfit, but she’s also kept her own quirky flare. The colored stripes up the side of the pants are an homage to her usually bright outfits while the scrunchy adds a touch of youthfulness. Those shoes are familiar, as we’ll see later on in this list.
Hailey certainly has a favorite type of heel, and it's these slip-on, chunky-heeled boot-like shoes.
They look comfortable and are so versatile. Not only do they match with this casual style she’s wearing, but they match other styles too. Also, can we gush about this jacket?! Talk about the most adorably sporty-chic choice.
19 Bold Pattern Choices Make Hailey Baldwin Stand Out From Other Celebs
Hailey Baldwin is certainly not one to hide from attention. While Billboard points out that she was homeschooled as a kid in order to retain her privacy, that hasn’t quite extended into her personal life. The way she dresses tells the world that Hailey is HERE! She’s bold, outgoing, and so genuinely creative that we can’t help but be inspired. We love the way she uses bold patterns in order to make a statement.
Blake Lively might be the queen of patterned suits right now, but Hailey Baldwin has been embracing them for ages now. This is rare in someone so young as well; it’s a good sign for the future, knowing that she’s going to be our style icon for many years to come.
18 Only She Can Make Oversized Athleisure Look So Cool
Athleisure is a trend that by now everyone has heard of. It’s been around for a few years and has been embraced by many stars, celebrities, and busy moms. Athleisure basically means wearing athletic clothes out and about during day to day life.
This could mean pieces like leggings or it could be something like cycling shorts - not to mention the jackets!
Bomber jackets and windbreakers are commonly reserved for running or cycling. Not anymore, according to Hailey Baldwin. She’s wearing them slightly oversized and looking oh so cool doing it. It’s enough to make us want to invest in cycling shorts and bright orange jackets too!
17 We're Pretty Sure Red Carpet Goes On The Ground, Not On Your Legs
This is one of the styles that we’re actually not a fan of, surprise surprise. Hailey Baldwin has had so many amazing red carpet styles, but this is definitely not one of them. We hate to say it, but red thigh-high boots should never make their way onto the red carpet. This is especially true when the boots are roughly the same texture as the carpet.
It looks like one long carpet piece has wrapped its way around Hailey Baldwin’s legs, and we’re not here for it. The dress itself is fine, but the shoes are just one of those statement pieces that really didn’t work out.
16 Though Her Glamour Looks Are Usually Red Carpet Rockstars
This is more like it. Hailey Baldwin normally has red carpet luxury down pat, as evidenced by this outfit. The bodysuit gives the illusion of her being clothed in black sparkly palm fronds. We’re super into it, even though it’s an outfit that we would never be able to pull off.
The style itself is quintessentially Hailey: it’s a little cheeky with a unique pattern and some sparkle to draw the eye to it.
It fits snugly in all the right places while still having a classy pant leg and cut. All in all, this red carpet version of a quirky Hailey Baldwin outfit is our total style inspiration for our next fancy party.
15 She's The Only One Who Can Pull Off This Print-Patterned Pantsuit
If Gucci is such a popular brand for celebs to show off, we see nothing wrong with Versace throwing their name all over a denim pantsuit. So why not just wear the Versace brand as a pattern? It certainly can’t be pulled off by just anyone, however, as the look is so bold that most wouldn’t be able to stand up to its attention-grabbing power.
Sometimes the clothes wear us, just due to how outgoing the print or fashion is. Luckily, Hailey Baldwin is a style goddess, which is why she’s able to pull off this bold and outgoing outfit. Matching patterns? Now that’s something we can definitely wear (even if they’re not Versace).
14 Baldwin Is Bold With Her Blazer Choices (And It Always Pays Off)
Seriously, is this an outfit or an amazing piece of wearable art? The blazer itself is what’s making our jaws drop, as the structure of this piece is amazing. The high shoulders and the bold lapels are perfectly balanced by the small buttons and clean lines.
Pairing it with a Baldwin signature hoodie underneath was an excellent choice, as it provides a great contrast to those shiny, leather-esque pants and puffy white heels.
It’s cozy, it’s bold, and it’s so undeniably Hailey that we can’t help but fall in love with it. She truly is iconic when it comes to mixing and matching pieces.
13 Not To Mention Those Baggy Pants And Tight T's She Rocks!
There are those same shoes again! These are the heels that seem to be Hailey Baldwin’s go-to shoe. They’re classic, clean, and match with simply everything. Here, she’s paired them with a neutral crop top, which is offset by a pair of baggy and distressed boyfriend jeans. It’s an outfit that’s so simple any of us could pull it off, though Hailey Baldwin certainly might pull it off the best.
This is a great example of her classic hair and makeup style, which is clean, simple, and straightforward. While she’s normally hidden behind sunglasses, the outfit doesn’t lose anything by not including them. It would be a cute addition, however, if it happens to be sunny out.
12 Her Slouchy Style Does Go Too Far Sometimes
Sometimes her crop top and baggy pant style can get a little out of hand. We hate to say it, but this is one Hailey Baldwin style that we’re just not into. It’s too casual, too baggy, and doesn’t have enough contrast to really work as a look.
It’s bold, for sure, but bold is only worth it if you can pull it off.
Unfortunately, Hailey Baldwin just hasn’t pulled this off. We’re hoping Justin Bieber’s style isn’t rubbing off on her too much; while it would be great for some of her style sensibilities to work their way into his wardrobe, we’ve had enough of the oversized pants.
11 With Cold Weather Coming, This Is A Look Almost Anyone Can Rock
This outfit is so normal and tame it hardly looks like Hailey under that hat! Believe it or not, that is a Hailey Baldwin style. The pant and jacket pairing is a strong choice. Both are earthy, and both really scream autumn.
We probably would choose a darker color of the hat, but only so it matches our shoes; which, by the way, seem to be a similar kind of heeled boots that she was wearing in some of the other photos. Hailey’s wardrobe isn’t just about the unique, bold styles. She’s also into the versatility and comfort of an outfit, which we can totally relate to.
10 Even Her Socks Are Coordinated - Now That's High Fashion
The edgier the better, apparently. This boss lady style features the perfect pairing of a slouchy, oversized graphic shirt and a leather rocker skirt. The accessories are totally on point, which is something we truly respect about Hailey Baldwin’s style.
She treats an outfit like the cohesive thing it is, utilizing those details to really pull off a look.
That’s the case in this style, at least, where she’s gone so far as to match her socks to her shirt, skirt, and other accessories. Details are a great way to tie a look together, and one that we’ll certainly be using on our next style adventure.
9 This Yellow Thing Has Us Yelling No, Though
Wait, what’s happening here? Why is everything yellow? What was Hailey Baldwin thinking when she put this on? While the color is a great summer style, there’s just so much of it. Some celebrities, like Kylie Jenner, are able to pull off the mono-color style. While we’re sure that Hailey Baldwin would be able to pull off the right kind of mono-color style, it’s certainly not this outfit.
The yellow basketball style shorts are just so in our face, and the yellow hoodie hides any and all shape. Keeping the hood up might be okay for privacy, but it’s definitely not great for style. We’d rather the outfit be styled differently, with a little less yellow and a little more… Fashion.
8 Mixing And Matching Might Be The Secret To Her Unique Looks
Mixing styles is part of the reason we look up to Hailey Baldwin so much. She’s not afraid to layer a blazer over top of a hooded sweatshirt and match it with some faux leather pants. The result is something that sounds scary but is actually incredibly flattering.
This is a great example of Hailey’s mix-and-match items style.
She’s got the sultry and silky yellow dress on underneath her cool, patterned bomber jacket. The result is something that’s got a lot of different textures, patterns, and styles to it. Need we point out the boots, also? It shouldn’t work, but it actually does. Really, really well.
7 She Certainly Isn't Afraid Of Real And Edgy
The shoes aren’t our favorite with this look, but we’re absolutely living for everything else. Not only does she have on the most adorable sweater dress, but she’s got this real and edgy jean jacket on. We’ve seen unique jean jackets on a couple celebs this season, and we’re expecting to see even more of them as we head into fall.
Hailey Baldwin is certainly doing it up right with these unfinished edges and distressed patches on her jacket. She effortlessly switches from sleek and polished blazers to edgy and distressed jean jackets. That’s just one of the reasons we’re such big fans of her style!
6 We're All For Bold, But This Mono-Color Combo Is Iconic For The Wrong Reasons
Remember when that yellow outfit popped up on the screen? This is an even bolder choice which we’re also not super into. While it’s a little more muted than the yellow that we saw above, the outfit itself is much more questionable. Yes, those sequin-styled skirts were popular for a while. Yes, oversized sweaters are a Hailey Baldwin signature style.
We get that she likes to be comfortable, but what happens when that comfort doesn’t quite align with the fashion statement it’s trying to make?
We love her baggy sweatshirts because they’re often a point of contrast; it provides dynamic visual interest to the outfit as a whole. This is one we’re just not seeing the dynamics of.
5 And This Abundance Of Fringe Isn't Any Better
Putting Gucci on it doesn’t make it okay. This outfit looks like a Coachella choice that accidentally made its way back into the real world. The bag is bubblegum pink while the rest of the ensemble is muted tones. It pops, but somehow just not in the right way. The shoes are another question mark, as we always thought jeans were meant to be worn as pants rather than as accessories.
We could definitely see her rocking that fringed sweater, but in a much different outfit than this. This doesn’t do any justice to Hailey Baldwin’s normal quirky fashion sense.
4 Her Always Defined Lines Give Us Style Envy In The Best Way
This is the Hailey Baldwin we know and love! It’s not just the clothes that can create dramatic shapes in an outfit: Baldwin knows the power of skin.
She artfully chooses which pieces to show and which pieces to hide and creates dynamics in her outfits depending on what parts she’s covering up.
The lines of her clothes are often very clean and sleek, like with this shirt. The collar is intense, but it shows off her collarbones well. While we don’t know if we’d be able to pull it off, the off-the-shoulder style is popular right now. It’s easily accessible and is definitely a style that we’d steal from Hailey.
3 She Owns A Million Amazing Jackets
Don’t believe us? Check out any photo from the last couple months. Hailey Baldwin has been rocking a strong jacket game, pulling off everything from oversized army jackets to athleisure articles. She’s got silky and sweet jackets as well as these dramatic, thick coats.
The designs on this one are unique and intricate and add a ton of visual interest to the outfit. It also makes it easy to match the rest of the outfit with, as there’s already a given color palette. We spotted those same shoes again, as well. Maybe we should pick up a pair, given how versatile they are.
2 She Makes Every Trend Match Her Own Style
Those cycling shorts have been a big hit or miss trend recently, which is why we’re so in awe of this outfit worn by the fabulous Hailey Baldwin. Not only has she decided to embrace the trend, but she’s made it her own.
She chose shorts in a jean material and paired them with a comfortable fisherman’s knit sweater.
The chunky top is the perfect match for this mid-length bottom, which looks perfect when paired with everyone’s favorite shoes. Her accessories tie the outfit together, making it a truly unique take on the recent cycling short trend. We don’t even miss the athleisure aspect!
1 At The End Of The Day, She's Definitely Had More Hits Than Misses
Sultry, quirky, and oh-so-stylish, Hailey Baldwin is constantly impressing us with her fashion choices. While her style isn’t everyone’s cup of tea, no one can deny the fact that she isn’t afraid to take style risks. We’re the first ones to admit that some risks turn out better than others.
Style is a funny thing, as it’s so personal it’s hard to say what’s right and wrong. We look up to Hailey Baldwin because she’s always true to her own style. She takes the current fashions and turns them into something she wants to wear, impressing us all with her creativity in the meantime. The one question we have for her: where does she buy her shoes? They’re consistently amazing.
References: Billboard, Teen Vogue, Elle
