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In her time as a model (and a style icon), Karlie Kloss has worn many, many outfits. So, it only makes sense that she would have discovered the perfect balance between chic, cute and casual—creating the ultimate look. Karlie Kloss’ suit and sneakers street style outfit proves that the model has uncovered the secret to creating this balance, and I am forever changed. Pulling off a suit can be hard on its own, but pulling off a suit with sneakers is even harder (at least for me). Karlie Kloss seems to have unlocked the code, though, showing her cute and casual fashion prowess with an Instagram outfit photo.

Posing in front of a California sunset, Karlie Kloss donned a simple two-piece suit, white tee and and white sneakers. Could it really be that easy? It seems that in all my efforts to figure out how to wear the right combination of boardroom-ready suiting and street style-approved sneakers, I got lost along the way. Well, Karlie Kloss is here to bring me (and all those with similar fashion quandaries) back to the street style promised land with this message: You’re overthinking it. Sometimes the best ensembles are the simplest ones—this suit and sneakers outfit included.

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That time of year when I fully consider moving to LA ☀️

A post shared by Karlie Kloss (@karliekloss) on Jan 28, 2020 at 8:51am PST

Basically, Karlie Kloss has given us all the ultimate formula to creating the ideal suit and sneakers look. Start simple and work your way up from there. It always helps to start with what you already have. Got a black suit hanging in your closet? Start by pairing it with a simple tee and sneakers you wear all the time. You’ll feel comfortable wearing items you already own, and can work up to playing it a little less safe. Wherever you are on the scale (of simple to maximalist, that is), Karlie Kloss’ street style look has proven that you’ll look great even in the simplest of ensembles.

Wide Leg Venice Crepe Trouser $89.95

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Kiki Double Breasted Blazer $95

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Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.l

If there’s one article of clothing my wardrobe must always have, no matter the season, it’s an oversized shirt. It could be a flannel, a button down, a band tee—Whatever it is, the only requirement is that it’s big. And while I thought I was good at pulling off this look, turns out Hailey Bieber’s oversized shirt street style outfit is here to knock me down a few pegs. Bieber seriously knows how to rock an oversized shirt, and I’m taking notes.

Leaving a dance class on Wednesday in Los Angeles, Hailey Bieber wore a simple cropped tank, rolled Champion sweatpants and a very, very cool orange plaid oversized flannel. The shirt hails from designer S.K. Manor, and is actually on sale for $162 right now. (It was originally $405.) So, go ahead and snag this oversized S.K. Manor flannel while you still can. The sunset hues in the shirt are perfect for any time of year—and orange is trending for 2020. It’s a win/win oversized situation.

Broadimage/Shutterstock.

Look—I know it isn’t necessarily difficult to pull off an oversized shirt look, but Hailey Bieber has it down to a science. Wearing a tank top or bralette under an unbuttoned top creates a cool contrast between the small shirt and the big shirt. And while adding sweatpants was a risky move (I’d usually go with something tighter like leggings or skinny jeans.), it paid off. The addition of the Nike sneakers that actually matched the colors in the oversized shirt plus the red Louis Vuitton bag just tied the whole ensemble together. This is no longer a workout look, but a seriously good street style outfit from Hailey Bieber. Color me impressed.

Broadimage/Shutterstock.

 

Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.l

As much as I love a good NYFW runway, I’m always most excited to see what people wear to the shows. Whether it’s celebrities, influencers or people lucky enough to snag an invite, these fashion show guests always know how to serve outfit inspiration for days. The New York Fashion Week Fall/Winter 2020 street style is yet another collection of impeccable ensembles that will have you questioning your own wardrobe—or at least trying to figure out how to use your own clothes to look that cool. From the latest trends to ensembles you’d never expect, the NYFW Fall/Winter 2020 street style is a delightful assortment of enviable looks.

I absolutely love to see what people wear to impress photographers, designers and the people at home (i.e. me!!!). Sometimes I think about what I might wear to fashion week, and the outfits I come up with are never as cool as those I see photographed. Maybe with some practice I could totally win the sartorial game, but until then, I’m happy just to get inspiration from those who are already at the top.

In this particular group of street style ensembles, you can expect to see several 2020 fashion trends. Matching sets are, of course, a popular look amongst fashion week goers. You’ll also see a lot of maximalist coats and many, many instance of perfectly balanced pattern clashing. Is it the year of the over-the-knee boot or something? Because there have been so many amazing of these shoe looks on the streets. You’ll see all these cool AF trends and more below in our favorite New York Fashion Week street style picks.

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Guest, New York Fashion Week Fall/Winter 2020 Street Style

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Guest, New York Fashion Week Fall/Winter 2020 Street Style

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Natasha Lyonne, New York Fashion Week Fall/Winter 2020 Street Style

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Guest, New York Fashion Week Fall/Winter 2020 Street Style

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Guests, New York Fashion Week Fall/Winter 2020 Street Style

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Guest, New York Fashion Week Fall/Winter 2020 Street Style

Hi, it’s me, the new Fashion & Lifestyle Editor here at StyleCaster. As a longtime beauty writer, making the switch to working in capital-F Fashion was more than a little bit daunting. Especially when you factor in that my first week on the job just so happened to be New York Fashion Week. I had to look office-appropriate, feel comfortable enough to run from show to show, and still be on-trend enough to get stopped for a few street style snapshots. It wasn’t easy to create the perfect street style outfits that still worked well for my first week as an ~official~ fashion editor, but according to my Instagram likes, I did a pretty good job.

I’d be lying if I said I woke up every morning of Fashion Week and threw on whatever thrilled me. It’s my first Fashion Week as an editor, not my first Fashion Week ever, y’all. I knew the drill! In reality, NYFW requires a lot of prep, and I had four key references when styling my looks. First, a few brands very kindly lent me pieces to be styled, which made a few of my outfits no-brainers. Second, my subscription to Rent The Runway really came in clutch, as I was able to wear an outfit to an AM show, drop it off at the Rent The Runway store, and have a new look delivered to my apartment for the very next day. Third, I thrifted a LOT of fun accessories. When you can’t splurge on designer duds, jazzing up your current wardrobe with unique thrift finds can really change the game. Last but not least, I had my very own closet, of course. There’s no better time to explore your own wardrobe and get creative with what you’ve already got than while prepping some NYFW slays.

Bella Gerard

Day One:

Here I am posing with my far-more-stylish friend, Belle! Afaf Zahira, the genius Creative Director of Heurueh, blessed me this (very cold) Fashion Week by lending me a few beautiful faux fur coats from her company. This pink-and-brown fur situation is my fave, and I wore it not once, but twice this week. While I’m all for wearing my fave pieces often on the reg, it’s rare to repeat during NYFW, so that says a lot about how much I loved this coat!

Because it was rainy and gloomy outside, I stuck with cheery bright pink but kept my overall look comfortable, with basic black boots and the Topshop Rose Long Sleeve Shirtdress. I paired it all with a classic black Chanel bag and a matching (lol) black umbrella. Since the look was so low-key, I really didn’t expect to get my photo taken, but because my friend, Belle, was also wearing a pink faux fur Heurueh coat, the photogs couldn’t get enough of us together. Shout out Will from @collectiveframes, aka my all-time fave street style photographer! Pro tip: If you’re scared to get your photo taken solo, coordinate with a friend.

Bella Gerard

Day Two:

‘Twas on this day that I snapped with a full athleisure fit. My joggers, long-sleeved shirt, and yellow bomber are all by Pyer Moss, and I rented the trio using my trusty Rent The Runway subscription. Y’all, I wouldn’t have survived Fashion Week without it! (Use my code RTRFAM11C7505 for a discounted membership if you feel the urge!) I styled the $1,035 three-piece set with some rain boots I picked up at River Island during a recent London trip, and avoided any rain-ruined hair by throwing mine up in a basic pony.

To distract from the underwhelming hairdo, I whipped up this black-and-yellow graphic eye look. I felt VERY nervous with the dramatic makeup and updo, but almost everyone I saw agreed this was my best look of the week. Good makeup can really make or break a ‘fit, y’all. To think, sweatpants and rain boots were my top NYFW slay!

Bella Gerard

Night Two:

When Day Two was winding down, a surprise landed on my desk. Okay, in my email inbox: a ticket to Christian Siriano’s Fall/Winter 2020 show. I was over the moon! I knew right away that I needed something a little more glam than my Pyer Moss athleisure look, so I ran home and threw on a look Victoria’s Secret had gifted me for just such an occasion. I paired one of their bustiers (The Lightly Lined Bustier is the most similar style currently available) with the stunning Button Midi Skirt in “Bronzed Olive” and grabbed one of my go-to thrift finds, a small black beaded evening bag. Was I cold? Yes. Did I slay? Yes. Zero regrets.

While I usually snag a second-row seat (Sometimes, for smaller shows, even front row!), I found myself fourth row for Siriano, a seat I was still thrilled to have. In fact, it gave me the perfect view of the star-studded front row across the way. I watched Heidi Klum, Alicia Silverstone, and Leslie Jones as closely as I watched the actual models—I even snapped this video of Leslie cheering on Coco Rocha, which then went viral, getting posted by Saint Hoax, InStyle, and even Christian Siriano himself. No big deal!!! (It was a very big deal.)

Bella Gerard

Day Three:

This outfit is brought to you by SKIMS Body Tape. Not really, but it should be, because I relied on it heavily to achieve this, um, perky look. Atop my tape I wore a Proenza Schuller Wildflower V-Neck Dress, which typically costs a cool $1650, but you guessed it, I scored it using Rent The Runway. I also rented the Diane Von Furstenberg Navy Soiree Top Handle Bag, thereby saving myself $548 bucks. I topped off my look with the Lele Sadoughi Sugar Petite Padded Candy Jeweled Headband, which got me approached by many a hair blog photographer whilst posing for street style photos. For a little contrast, I threw on the Steve Madden Kinga Boot in “Blue Snake.” I wouldn’t normally clash like this in my daily life, but at Fashion Week, anything goes!

It was in this outfit that I answered some questions for a Jimmy Kimmel segment, in which I knew I would most likely get made fun of, because, well, that’s what Jimmy Kimmel segments are all about. He asked questions about baseball scandals and my friend (Belle again!) and I could only respond with “Huh?!” on repeat. Looking back at the clip now, though, the most embarrassing part was my not-so-TV-appropriate cleavage. I loved this look, but will not be wearing it again, LOL.

Bella Gerard

Day Four:

On this day, I was generously gifted a look by Petite Studio, a brand that caters specifically to petite bodies. This was especially cool as someone who doesn’t have the tall-and-skinny model body type so often seen at fashion-related events (Do better, NYFW!). As a 5’1 curvy gal, I was beyond excited to give their stuff a go, and I was ultimately quite pleased with my picks. I snagged this blue-and-stone-colored set from the brand’s coming-soon Spring collection, and inspired by the color-blocking, I paired one of my Steve Madden blue Kingas with one stone-colored boot from the depths of my closet. I cinched my waist with a white fur Moschino belt I gifted myself for my birthday last year from Nordstrom Rack.

This look is not my usual style, and I admit, I was a little nervous to see what people would think. Especially because of the boots! I did a poll on my Instagram Stories asking how people felt about the mismatched shoes (So very Carrie Bradshaw, if I do say so myself!) and 73% of voters were in favor. I doubt I’d try it again, but I’m glad it was a hit.

Bella Gerard

Day Five:

Five days in, my incredible hot pink Heurueh coat made its second appearance. Get a load of that lining! This time around, I paired it with the Topshop Floral Ditsy Flounce Midi Skirt and the Marissa Webb Emmerson Oxford Shirt. Another rainy day, I kept my shoes simple with comfortable black boots and saved my hair from frizz with the Lele Sadoughi Jet Mixed Crystal Headband.

This look was so low-key, but it ended up being a great lesson in accessories: making my basic button-down and skirt Fashion Week ready was easy with a bold coat and hair accessory! If there were two standout staples for me this fashion week, they were faux fur and funky headbands. I was mostly backstage checking out the shows’ beauty looks for StyleCaster on this day, but when a last-minute change allowed me to stay for the Libertine show, I still felt glam enough to attend.

Bella Gerard

Night Five:

Is it obvious that I went to Topshop before Fashion Week began? Here I am in yet another Topshop piece, the Smudge Mesh Long Sleeve Midi Dress, which gave me serious Fuzzi vibes. I reached for my classic black Chanel bag yet again, plus the Steve Madden Dakota boots in “Black Suede,” and bam! A look was born! As you can tell by the photo, I was really feeling myself.

That said…At this point in the week, my friends and Insta followers were hardcore gassing me up, and I had over 200 DMs praising my cool new job, my stylish outfits, and my “super fun life.” A reality check for anyone who felt that way: My feet were KILLING me, I was majorly stressing about if I was over-posting, and after being surrounded by models and fashion’s elite all week, I did not feel very cute. Instagram is a very fun highlight reel, but don’t be fooled. I love Fashion Week, but there’s more (stress) than meets the eye!

Bella Gerard

Day Six:

Ah, the final day. I woke up with shin splints after a week of running around! Because of this, I paired my nautical-business-casual look with my Puma Rise Sneakers, and while I was worried I’d be judged for not wearing heels or boots, I actually received a ton of compliments. Who would’ve thought! Up top, I had on two Rent The Runway gems I paired together: this Tory Sport Breton Stripe Knit Skirt, originally $248, and the Victoria / Tomas Green Striped Blazer, originally $155. I’m also wearing a graphic tee from Anthropologie that I found in the sale section, which features drawings of Oprah Winfrey and Anna Wintour with the phrase “Win-Win.” How iconic is that? I also wore a simple, braided black headband, because if you haven’t been able to tell, I wasn’t in the mood to wash my hair this week. What can I say, Fashion Week is exhausting!

Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale and the retailer may receive certain auditable data for accounting purposes.

Bella Hadid may wear some ridiculously good ensembles on the runway, but her street style is arguably just as chic. After an incredibly successful time strutting in both New York Fashion Week and London Fashion Week, the model has moved on to Milan Fashion Week—where she has (once again) become our sartorial queen. Bella Hadid’s Milan Fashion Week 2020 street style has been the perfect mix of trendy and mind-boggling. It’s everything a gal looking for some outfit inspiration could want—and so much more.

I’ve been watching Bella Hadid tear up the Milan Fashion Week runways, but she’s also been tearing up my heart (Was that too cheesy? Get over it.) with these incredible street style ensembles. I rounded up all of her drool-worthy looks (and added some commentary, because who do you think I am?), so you can see just exactly how good these outfits are. I’m not sure what kind of power the Hadid gals have over me (Because we can’t forget Gigi!), but I might actually be into the tiny sunnies trend now. These Milan Fashion Week Fall/Winter 2020 street style looks are too powerful, you guys.

Laurent Vu/SIPA/Shutterstock.
Bella Hadid leaving a Versace fitting
Bella Hadid out and about, Milan Fashion Week, Italy – 20 Feb 2020

Leaving a Versace fitting — February 20

Let me just talk about this argyle sweater, y’all. Typically, when I think of argyle, I think of a grandpa rolling around town with his walker. I do not think supermodel street style. Yet here we are, and Bella Hadid has made an argyle sweater look cooler than I could have ever imagined. With giant gold hoops and ombre brown pants, I’d say this one surprisingly successful look.

Laurent Vu/SIPA/Shutterstock.
Fendi show, Departures, Fall Winter 2020, Milan Fashion Week, Italy – 20 Feb 2020

Leaving Fendi Show — February 20

Look, I know we already saw part of this ensemble, but it’s always important to take a second look. After all, this time we get to see that the argyle sweater is actually a sweater vest. And frankly, it looks just as good on Bella Hadid without a jacket as it does with one.

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Bella Hadid out and about, Milan Fashion Week, Italy – 21 Feb 2020

Out and About — February 21

What’s a street style round-up without an oversized blazer or two? Bella Hadid stepped out in Milan in what may be my new go-to ensemble. You truly can’t go wrong when you pair a chic graphic tee (In the case of Bella Hadid, a tee with a children’s storybook character? I’m unsure what’s going on here, but I like it.) with a huge blazer. It’s just a classic look, and the statement earrings definitely amp it up.

Laurent Vu/SIPA/Shutterstock.
Versace show, Arrivals, Fall Winter 2020, Milan Fashion Week, Italy – 21 Feb 2020

Arriving at Versace Show — February 21

We love a good quick change. Bella Hadid wore two different outfits today, and this embroidered sweater look is drastically different from her previous oversized blazer outfit. Once again, Hadid seems to be rocking the sweater your grandparents might wear, but she makes it absolutely cool as hell.