An Ode To Iconic Street Style Outfits, Since This Year’s Fashion Month Has Gone Digital

Maggie Griswold
An Ode To Iconic Street Style Outfits, Since This Year’s Fashion Month Has Gone Digital
Photo: IMaxTree.

There are plenty of great places to search for fashion and outfit inspiration—Pinterest, Instagram, StyleCaster (wink, wink)—but sometimes you just want all of the best street style looks in one place for whenever you’re not feeling what’s in your closet. Even the most stylish folks occasionally need a little boost of inspo (After all, they weren’t just born knowing the latest trends and how to style them all.), so having a go-to list of outfit ideas is a must. Thankfully, you have us to supply it. You’re welcome!

Because of the sheer number of incredible looks from year to year, it’s nearly impossible to pick and choose the best street style outfits—but we’ve discovered some truly iconic ensembles. Though nearly every outfit from the streets of Paris Fashion Week, New York Fashion Week, Milan Fashion Week and beyond deserves a moment in the sun, there are always stand-outs. You truly never know what kind of looks you’ll get when Fashion Month starts, but you can always count on them being absolutely jaw-dropping.

There are plenty of different types of looks we typically see in street style collections, though, so let’s take a moment to unpack them, shall we? There are always—and we mean always—the folks who dress totally inappropriately for the temperatures outside. Pain in the name of fashion is a big trend, apparently. Whether that’s swearing a mini dress when it’s freezing or a giant coat when it’s sweltering outside, you can always expect some looks that don’t fit with the season. (They still look good, though.)

Then, there are those who go totally maximalist. Bold pattern mixing, bright makeup, wild hair—you name it. There’s nothing off-limits for these street style enthusiasts, and they always boast some of the best outfits. These ensembles aren’t usually the kinds you can recreate in-full for an average day on the town, but they’re definitely fun to peruse.

On the opposite end of the spectrum, you can always find quite a few minimalist outfits, too. These folks take current trends and keep them super simple. This could mean an oversized blazer paired with a turtleneck and maybe a pop-of-color bag or a trendy dress in a neutral hue paired with accessories of the same color. While these looks might not be the most exciting, they’re totally wearable—making for great everyday outfit inspiration.

You also have the wild cards. Sometimes, fashion show attendees will appear wearing the most outrageous ensembles that don’t necessarily hint at upcoming or current trends—or even past trends, TBH. They’re there to put on a show, and we will happily sit back and watch them do their thing.

Of course, what trends these folks might wear changes from year to year, but there are always fashionistas in these categories—so make sure to watch out for each. Knowing which outfits are more accessible and which will likely stay on your fashion Pinterest boards and not in your closet can be helpful when perusing the best street style. So without further ado, keep scrolling for an incredible amount of swoon-worthy street style inspiration.

 

STYLECASTER | Best Street Style

IMaxTree.

Sunset hues on sunset hues. Going with red and orange for a bold look is a great choice—and those ruffly sleeves don’t hurt, either.

 

STYLECASTER | Best Street Style

IMaxTree.

Play with mixing two of the same patterns in different colorways. This plaid-on-plaid outfit is truly masterful.

 

STYLECASTER | Best Street Style

IMaxTree.

A head-to-toe bright animal print suit? It’s chicer than we ever thought it could be. Keep your accessories simple with this one, though.

 

STYLECASTER | Best Street Style

IMaxTree.

Winnie Harlow can do no wrong, and she looks absolutely stunning in this neutral outfit. Don’t be afraid to go for a bold shoe choice—like these ridiculously tall boots Harlow wore.

 

STYLECASTER | Best Street Style

IMaxTree.

Colorful leather looks are always a good option. Try different colors together to see which you like best! This green, yellow and brown ensemble is gorgeous.

 

STYLECASTER | Best Street Style

IMaxTree.

You can’t go wrong with a maximalist fuzzy coat! Big Bird, but make it fashion.

 

STYLECASTER | Best Street Style

IMaxTree.

There are so many different ways to mix patterns, but wearing two bold prints together is typically a choice that pays off—at least during Fashion Week.

 

STYLECASTER | Best Street Style

IMaxTree.

If you’re unsure what accessories you can use to spice up your ensemble, try styling your favorite scarf different ways.

 

STYLECASTER | Best Street Style

IMaxTree.

Once again, sunset hues are always so good. If you’re not sure how to style them, try an easy color-blocked look.

 

STYLECASTER | Best Street Style

IMaxTree.

Take your sheerest pieces to the next level by wearing them without a slip. Instead, pair a long sheer skirt with a shorter skirt underneath for a cool peek-a-boo vibe.

 

STYLECASTER | Best Street Style

IMaxTree.

Don’t be afraid to play with colors! We wouldn’t typically put mustard yellow and red together, but done well—like in the ‘fit above—it’s seriously stunning.

 

STYLECASTER | Best Street Style

IMaxTree.

When in doubt, throw on your favorite long trench coat with a sleek turtleneck and trousers look for an effortless ensemble that’s perfect for fall and winter.

 

STYLECASTER | Best Street Style

IMaxTree.

Think you can’t make pajamas into a street style look? Think again. Choose a cute silky set, then add a pair of white sneakers and oversized sunnies.

 

STYLECASTER | Best Street Style

IMaxTree.

Going monochrome is always a fun choice. Make it bold by choosing to wear a bright color—like neon orange or green.

 

STYLECASTER | Best Street Style

IMaxTree.

If you don’t want to go full monochrome, you can still opt for a matchy-matchy vibe. Coordinate all the colors in your ensemble for an outfit that’s ridiculously cool.

 

STYLECASTER | Best Street Style

IMaxTree.

Yes, pregnant street style looks exist—and they’re so cute. Just because you’re expecting doesn’t mean you can’t rock something incredibly chic.

 

STYLECASTER | Best Street Style

IMaxTree.

Mixing two animal prints is a bold move, and we’re so into it. Most animal prints actually go well together, so take the risk and try it out with your own wardrobe.

 

STYLECASTER | Best Street Style

IMaxTree.

Even if you don’t have a lot of bold footwear, you can still spice things up by wearing chic sheer socks with your favorite heels.

 

STYLECASTER | Best Street Style

IMaxTree.

Go for a vintage vibe by tying a scarf around your head and adding a pair of oversized sunglasses. It’s very old-school convertible chic.

 

STYLECASTER | Best Street Style

IMaxTree.

In street style, anything goes—which means you can even get away with wearing fuzzy slippers out and about. Yes, please.

 

STYLECASTER | Best Street Style

IMaxTree.

Neutral monochrome looks don’t have to be minimalist or boring. Find exaggerated and cool pieces in neutral colors and watch as they create a totally unique ensemble.

 

STYLECASTER | Best Street Style

IMaxTree.

You can always keep things simple (like an all-black look), then add a neon coat for a pop of color. You’ll stand out without overdoing it.

 

STYLECASTER | Best Street Style

IMaxTree.

Yes, cardigans can work for street style looks. Wear a patterned cardigan as a top with some fun trousers, and you’ve got a gorgeous outfit on your hands.

 

STYLECASTER | Best Street Style

IMaxTree.

Don’t sleep on tights, folks! Especially during fall and winter, colorful tights can take a “meh” outfit and turn it into a street style dream.

 

STYLECASTER | Best Street Style

IMaxTree.

Street style is all about attitude, so even a classic black jeans and boots look can be turned into a can’t-miss ensemble with the help of a neon top and a little confidence.

 

STYLECASTER | Best Street Style

IMaxTree.

Warmth, but make it street style-appropriate. Big puffer coats are a great way to stay warm while also looking cool AF. Try a bold color for an even sleeker look!

 

STYLECASTER | Best Street Style

IMaxTree.

A graphic tee is something that can easily be turned into a street style look as well. Try wearing your favorite with a cool skirt, fun shoes and unique sunglasses. (Accessories are important, people!)

 

STYLECASTER | Best Street Style

IMaxTree.

You can never go wrong with a cool oversized blazer. Keep it open or button it up, then add fun accessories to top it all off.

 

STYLECASTER | Best Street Style

IMaxTree.

If you find an article of clothing you think might be too maximalist, wear it anyway. With a street style mindset, you can pull off just about anything.

 

STYLECASTER | Best Street Style

IMaxTree.

Don’t ask us why, but this giant bag is a mood. Maybe it’s not an everyday look, but it’s certainly the amount of storage we wish we had in our purses.

 

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