Literally Just 101 of the Prettiest Fall Street Style Photos We’ve Ever Seen

Lindsey Lanquist
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Literally Just 101 of the Prettiest Fall Street Style Photos We’ve Ever Seen
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Photo: Christian Vierig/Getty Images.

Bidding adieu to warm weather is never easy. The tingle of summer heat is almost always preferable to the frigid bite of winter, and snuggling fall between the two leaves the transitional season feeling more dreadful than inviting for many.

Trading swimsuits for sweaters feels like a chore—one that suggests it’ll be six long months before your sandals, sunglasses and swim cover-ups have meaning again. (Or that you’ll be spending the next 182 days trapped indoors, lest you go outside and slip on the icy sidewalks surrounding your home.)

MORE: A Definitive Guide to Sweaters That Are as Cozy as They Look

This line of thinking makes sense—but it’s terribly misguided. Fall might be sandwiched between two extremes, but it offers the best of both of them. When else can you embrace cozy, cold-weather knits in a vibrant, warm-weather color palette? Or pair your snuggliest sweats with your comfiest slides? Or wear a scarf and boots with your sundress, because it’s too warm for pants but too cold for sandals?

Fall is a season of lighting candles, sipping beverages from kitschy mugs, taking warm baths and cozying up with your favorite blankets. For the first time in months, summer’s oppressive humidity lifts, and you’re able to snuggle with bae without working up a sweat.

And though winter looms near, the weather is actually incredibly moderate. Even in December (a month mostly in fall—mind you) often, you can step outside in a sweatshirt and leggings (read: not your heaviest coat) and feel totally fine.

MORE: The Easiest Way to Stock up on Hygge: Mix and Match Cute Mugs

If you’re not excited for fall, you’re doing it wrong. (I’m not totally sure what it is. Life, maybe?) But in case the images we’ve conjured of candle-lighting, tea-sipping, bath-taking and bae-snuggling haven’t gotten you on board, perhaps the following 101 fall photos will.

Ahead, you’ll find a gallery full of autumn street style inspiration. Because if you’re not looking forward to cooler weather, you’ve clearly forgotten the undeniable magic a fall wardrobe can work.

A version of this story was originally published in August 2014.

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STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Warm enough for patchwork skirts. Cool enough for fur-trimmed jackets.

Photo: Cladio Lavenia/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Can't choose between your long-line silky jacket and your boxy wool one? It's breezy out—wear both.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Winter tweed rendered in a summery palette.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

That statement coat you bought is too nice for actual snow. Whip it out now, instead.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

A quick reminder that statement sunnies have a place in fall fashion, too.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The only season when it's appropriate (and honestly, practical) to drape your trench over your shoulder—rather than, you know, wearing it.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Yellow won't skew "Easter brunch" when you wear it in October.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Denim on denim won't leave you sweating when it's 50 degrees out.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Proof maxi dresses and fall aren't mutually exclusive.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Why not pull sartorial inspiration from the pile of leaves you just jumped in?

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Is it just us, or does athleisure get way cozier when you throw a coat over it?

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Update: It's definitely not just us.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Can you think of another time of year when dressing like the high-fashion equivalent of a schoolgirl is encouraged?

Photo: Melodie Jeng/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

It's all-velvet-everything season.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because miniskirts pair best with thigh-high boots. And thigh-high boots are too hot for warm weather.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Outfit feels incomplete? Throw on a layer. Still feels incomplete? Throw on another.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Unpack those plaid shirts you retired during the summer, because it's their time to shine.

Photo: Mireya Acierto/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Fringe, leather, suede—let's go.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

If you own a kilt, now's probably the time to take it for a spin.

Photo: Claudio Lavenia/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Hope your leather jacket didn't get too dusty during those warmer months.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Power suits are more temperature-appropriate during the fall. It's a simple fact.

Photo: Mireya Acierto/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Office-appropriate outfits are easier to figure out when it's cold enough for pants.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Pair orange with black without worrying if it looks too Halloween. Because guess what—it's OK if it does.

Photo: Melodie Jeng/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

I'm sorry, can you wear sock boots during the summer? Didn't think so.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The time of year when snuggly coats are as cozy as your softest blanket.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Not sure what to wear? Your handy-dandy turtleneck will get you through the day.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Snakeskin coats: Too edgy for spring, too hot for summer, too lightweight for winter—just right for fall.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Bring on the puffer vests.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Throw a shearling coat over anything, and you'll be set.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Fall florals—it's a thing.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Animal print matching sets look better over turtlenecks. And turtlenecks look best when it's cold out.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

I mean, she's wearing a plaid coat. Can you think of anything more distinctly fall?

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Graphic fur coats and vinyl pants: the style star's method of staying warm on windy days.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

To paraphrase Spongebob: The best time to wear an oversized sweater is all the time.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because your go-to maxiskirt's a lot more fun when it's covered in preppy fall layers.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Autumn's favorite tailored coats will add instant polish to any look.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Did someone say achromatic ensemble season?

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The only time of year when it's actually advisable to pair puffy coats with open-toed shoes.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

If you don't dream up the avant-garde equestrian looks you plan to wear all season long, you're doing it wrong.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Suede, shearling and denim—oh my.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because coats are more badass when they graze the floor.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Work those jewel tones.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

High fashion's take on the fall sweatsuit is even cuter (and honestly, warmer) than you remember.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Take your favorite warm-weather look from summer to fall in one step: Add a trench.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Button-down, meet turtleneck. Turtleneck, meet button-down. You're a bona fide match made in heaven.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

If there's one time of year when camo doesn't feel costumey, it's fall.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

What's too heavy for summer, but too floor-draggy for winter snow? You guessed it—your favorite oversized pantsuit. Why not make Hillary Clinton proud and pull it out now?

Photo: Vanni Bassetti/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Heavy layers demand heavy jewelry. (So give yourself the excuse to go shopping.)

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Draw inspiration from the pumpkins adorning your living room—we won't judge.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Consider this the corduroy version of the Canadian tuxedo. While you're at it, consider how great it looks, too.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The easiest way to dress during those it's-cold-but-not-so-cold days? Your favorite sweater, paired with your favorite maxiskirt.

Photo: Claudio Lavenia/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Mixing prints gets a lot easier when your tried-and-true coat features a tight plaid.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Berets, leather skirts and studded boots—embrace it all.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The next time you want to look straight off the runway, wear half your trench coat, and tie the other half around your waist like a belt. Now that's something you definitely couldn't do in the summer.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because your feathers would get wet (with sweat or snow) during any other season.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Why retire your sunnies until spring break when you could wear them all fall long, instead?

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

If it doesn't make us look like the high-fashion version of the Michelin man, we don't want to wear it.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Wear a hat without worrying about your head overheating. Because you can.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

In fall, even the most I-just-rolled-out-of-bed looks skew trendy.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

All-black-everything is the unofficial uniform of the season—embrace it.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

A Lucite trench over a camel trench? Can you think of anything more fall/winter 2018?

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Animal prints and plaid are both huge this season—take advantage of the opportunity to mix and match them without looking like you got dressed in the dark.

Photo: Claudio Lavenia/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Heavy dressed and open-toed shoes don't have to be oxymoronic when combined—at least, not in autumn.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Basically your favorite seasonal trench coat transformed into a power suit. Who's complaining? (We're not.)

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because some days you want to wear a trench coat with shorts. And in fall, you can.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Navies and plums are in high demand, and we're not mad about it.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

PSLs are in full force. Might as well derive a little outfit inspo from them.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

As the leaves begin to turn, so, too, do the colors of our outfits.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The only season where a broutfit (brown-outfit—keep up) doesn't feel blasé.

Photo: Vanni Bassetti/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

In the summer, jumpsuits are your one-stop shop for style. In the fall, coats are.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Pairing a sweatshirt with your favorite heeled booties isn't ill-advised when it's cool out. It's sensible.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Pops of color are way more fun when your entire world is rendered in autumnal shades of brown.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Something about the blazer/crossbody combo just works.

Photo: Kirstin Sinclair/Getty Images.

Dress down your favorite faux fur with sneakers. Alternatively, dress up your favorite sneakers with a little faux fur.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Whoever said crop tops were off the table once jacket season began clearly didn't know what they were talking about.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

How to wear white after Labor Day (and look good doing it).

Photo: Melodie Jeng/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because it's fun to break up black-on-black with a pop of color. Even if that pop of color is gray.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Repeat after me: Clunky footwear—specifically, clunky footwear with good traction—is your friend.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Sweaters, leather pencil skirts and block heels are a class combination you can turn to whenever you find yourself sartorially stumped.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Leggings aren't just for warm weather wear. Slip into your favorite trench and keep the legging train going all season long.

Photo: Edward Berthelot/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Give your retro shearling coat an updated feel with mod accessories. Or don't. It's pretty hard to go wrong with something so classically comfy.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Your printed pants aren't exclusively reserved for warm weather. Throw on a jacket and make them breezy-day-appropriate, too.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Officially convinced we need an animal-print blazer and matching trousers. Is this the new power suit?

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Proof your outfit doesn't have to be colorful to look interesting.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Baker boy caps look even better when paired with fuzzy outerwear. (Trust us, summer only gave you a mere glimpse at their potential.)

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Why stress about combining saturated shades when you could pair neutrals and look this good?

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Beret-wearing isn't just permitted this fall. It's hip.

Photo: Matthew Sperzel/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

A going-out ensemble that walks the line of cooling you down and warming you up.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Power suits look great with turtlenecks, and don't you forget it.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

All-slouchy-everything looks put-together when you're wearing a coat (and sunglasses).

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The only fall basics you need.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Tired of wearing a scarf around your neck? Drape it over your shoulder. It's warm enough that you can afford to.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The easiest (and comfiest) way to dress like a model.

Photo: Melodie Jeng/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

When dressed in gold, you'll look opulent 24/7.

Photo: Vanni Bassetti/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

A colorless outfit doesn't have to be boring. Play with the silhouettes of your pieces, instead.

Photo: Timur Emek/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

A jet-set look so trendy you'll never want to change out of it.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Your coat can double as a dress if you really want it to.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

The easiest way to dress up cargos: Throw on a leather jacket.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Because pumpkin-colored shoes are almost more fun than actual pumpkins.

Photo: Kirstin Sinclair/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Snow boots can be your more statement-making accessory if you work at it a little.

Photo: Christian Vierig/Getty Images.
STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

Soft tees. Fur coats. Velvet pants. Can you think of anything cozier? We can't.

Photo: Christian Vierig/Getty Images.

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  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
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  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
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  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen
  • STYLECASTER | 101 of the Best Fall Street Style Photos We've Ever Seen

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